diff --git a/core/src/main/java/org/jruby/RubyComplex.java b/core/src/main/java/org/jruby/RubyComplex.java
index 19e05a48580..691bf783570 100644
--- a/core/src/main/java/org/jruby/RubyComplex.java
+++ b/core/src/main/java/org/jruby/RubyComplex.java
@@ -1289,8 +1289,8 @@ static IRubyObject[] str_to_c_internal(ThreadContext context, RubyString str) {
 
         if (m != nil) {
             RubyMatchData match = (RubyMatchData)m;
-            sr = match.at(1);
-            si = match.at(2);
+            sr = match.at(context, 1);
+            si = match.at(context, 2);
             re = match.post_match(context);
             po = true;
         }
@@ -1301,9 +1301,9 @@ static IRubyObject[] str_to_c_internal(ThreadContext context, RubyString str) {
             if (m != nil) {
                 RubyMatchData match = (RubyMatchData)m;
                 sr = nil;
-                si = match.at(1);
+                si = match.at(context, 1);
                 if (si == nil) si = runtime.newString();
-                IRubyObject t = match.at(2);
+                IRubyObject t = match.at(context, 2);
                 if (t == nil) t = runtime.newString(RubyInteger.singleCharByteList((byte) '1'));
                 ((RubyString) (si = si.convertToString())).cat(t.convertToString());
                 re = match.post_match(context);
@@ -1315,12 +1315,12 @@ static IRubyObject[] str_to_c_internal(ThreadContext context, RubyString str) {
             m = RubyRegexp.newDummyRegexp(runtime, Numeric.ComplexPatterns.comp_pat2).match_m(context, str, false);
             if (m == nil) return new IRubyObject[] { context.nil, str };
             RubyMatchData match = (RubyMatchData) m;
-            sr = match.at(1);
-            if (match.at(2) == nil) {
+            sr = match.at(context, 1);
+            if (match.at(context, 2) == nil) {
                 si = context.nil;
             } else {
-                si = match.at(3);
-                IRubyObject t = match.at(4);
+                si = match.at(context, 3);
+                IRubyObject t = match.at(context, 4);
                 if (t == nil) t = runtime.newString(RubyInteger.singleCharByteList((byte) '1'));
                 ((RubyString) (si = si.convertToString())).cat(t.convertToString());
             }
diff --git a/core/src/main/java/org/jruby/RubyGlobal.java b/core/src/main/java/org/jruby/RubyGlobal.java
index c1db1859d2f..fae5d88b7e6 100644
--- a/core/src/main/java/org/jruby/RubyGlobal.java
+++ b/core/src/main/java/org/jruby/RubyGlobal.java
@@ -918,7 +918,8 @@ public PreMatchGlobalVariable(Ruby runtime, String name) {
 
         @Override
         public IRubyObject get() {
-            return RubyRegexp.match_pre(runtime.getCurrentContext().getBackRef());
+            var context = runtime.getCurrentContext();
+            return RubyRegexp.match_pre(context, context.getBackRef());
         }
     }
 
@@ -940,7 +941,8 @@ public LastMatchGlobalVariable(Ruby runtime, String name) {
 
         @Override
         public IRubyObject get() {
-            return RubyRegexp.match_last(runtime.getCurrentContext().getBackRef());
+            var context = runtime.getCurrentContext();
+            return RubyRegexp.match_last(context, context.getBackRef());
         }
     }
 
diff --git a/core/src/main/java/org/jruby/RubyMatchData.java b/core/src/main/java/org/jruby/RubyMatchData.java
index a249c1a22ee..57ef9f804c9 100644
--- a/core/src/main/java/org/jruby/RubyMatchData.java
+++ b/core/src/main/java/org/jruby/RubyMatchData.java
@@ -34,11 +34,6 @@
 
 package org.jruby;
 
-import java.util.Arrays;
-import java.util.Iterator;
-import java.util.stream.Stream;
-import java.util.stream.StreamSupport;
-
 import org.jcodings.Encoding;
 import org.joni.Matcher;
 import org.joni.NameEntry;
@@ -46,8 +41,8 @@
 import org.joni.Region;
 import org.joni.exception.JOniException;
 import org.joni.exception.ValueException;
-import org.jruby.anno.JRubyMethod;
 import org.jruby.anno.JRubyClass;
+import org.jruby.anno.JRubyMethod;
 import org.jruby.ast.util.ArgsUtil;
 import org.jruby.runtime.Arity;
 import org.jruby.runtime.Block;
@@ -60,11 +55,22 @@
 import org.jruby.util.RegexpOptions;
 import org.jruby.util.StringSupport;
 
+import java.util.Arrays;
+import java.util.Iterator;
+import java.util.stream.Stream;
+import java.util.stream.StreamSupport;
+
 import static org.jruby.api.Convert.asFixnum;
 import static org.jruby.api.Convert.asSymbol;
-import static org.jruby.api.Create.*;
+import static org.jruby.api.Create.newArray;
+import static org.jruby.api.Create.newEmptyArray;
+import static org.jruby.api.Create.newEmptyString;
+import static org.jruby.api.Create.newRawArray;
+import static org.jruby.api.Create.newSmallHash;
+import static org.jruby.api.Create.newString;
 import static org.jruby.api.Define.defineClass;
 import static org.jruby.api.Error.argumentError;
+import static org.jruby.api.Error.indexError;
 import static org.jruby.api.Error.typeError;
 import static org.jruby.util.RubyStringBuilder.str;
 
@@ -281,29 +287,29 @@ public final boolean used() {
         return (flags & MATCH_BUSY) != 0;
     }
 
-    final void check() {
-        if (str == null) throw typeError(getRuntime().getCurrentContext(), "uninitialized Match");
+    final void check(ThreadContext context) {
+        if (str == null) throw typeError(context, "uninitialized Match");
     }
 
-    final Regex getPattern() {
+    final Regex getPattern(ThreadContext context) {
         final Object pattern = this.pattern;
-        if (pattern instanceof Regex) return (Regex) pattern;
-        if (pattern == null) throw typeError(getRuntime().getCurrentContext(), "uninitialized Match (missing pattern)");
+        if (pattern instanceof Regex regex) return regex;
+        if (pattern == null) throw typeError(context, "uninitialized Match (missing pattern)");
         // when a regexp is avoided for matching we lazily instantiate one from the unquoted string :
-        Regex regexPattern = RubyRegexp.getQuotedRegexpFromCache(metaClass.runtime, (RubyString) pattern, RegexpOptions.NULL_OPTIONS);
+        Regex regexPattern = RubyRegexp.getQuotedRegexpFromCache(context, (RubyString) pattern, RegexpOptions.NULL_OPTIONS);
         this.pattern = regexPattern;
         return regexPattern;
     }
 
-    private RubyRegexp getRegexp() {
+    private RubyRegexp getRegexp(ThreadContext context) {
         RubyRegexp regexp = this.regexp;
         if (regexp != null) return regexp;
-        final Regex pattern = getPattern();
-        return this.regexp = RubyRegexp.newRegexp(metaClass.runtime, (ByteList) pattern.getUserObject(), pattern);
+        final Regex pattern = getPattern(context);
+        return this.regexp = RubyRegexp.newRegexp(context.runtime, (ByteList) pattern.getUserObject(), pattern);
     }
 
     private RubyArray<?> match_array(ThreadContext context, int start) {
-        check();
+        check(context);
 
         if (regs == null) {
             if (start != 0) return newEmptyArray(context);
@@ -323,27 +329,40 @@ private RubyArray<?> match_array(ThreadContext context, int start) {
         return arr.finishRawArray(context);
     }
 
+    @Deprecated(since = "10.0")
     public IRubyObject group(long n) {
-        return RubyRegexp.nth_match((int)n, this);
+        return group(getCurrentContext(), (int) n);
     }
 
+    @Deprecated(since = "10.0")
     public IRubyObject group(int n) {
-        return RubyRegexp.nth_match(n, this);
+        return group(getCurrentContext(), n);
     }
 
+    public IRubyObject group(ThreadContext context, int n) {
+        return RubyRegexp.nth_match(context, n, this);
+    }
+
+    @Deprecated(since = "10.0")
     public int getNameToBackrefNumber(String name) {
+        return getNameToBackrefNumber(getCurrentContext(), name);
+    }
+
+    public int getNameToBackrefNumber(ThreadContext context, String name) {
         try {
             byte[] bytes = name.getBytes();
-            return getPattern().nameToBackrefNumber(bytes, 0, bytes.length, regs);
+            return getPattern(context).nameToBackrefNumber(bytes, 0, bytes.length, regs);
         } catch (JOniException je) {
-            throw metaClass.runtime.newIndexError(je.getMessage());
+            throw indexError(context, je.getMessage());
         }
     }
 
     // This returns a list of values in the order the names are defined (named capture local var
     // feature uses this).
+    @Deprecated(since = "10.0")
     public IRubyObject[] getNamedBackrefValues(Ruby runtime) {
-        final Regex pattern = getPattern();
+        var context = runtime.getCurrentContext();
+        final Regex pattern = getPattern(context);
         if (pattern.numberOfNames() == 0) return NULL_ARRAY;
 
         IRubyObject[] values = new IRubyObject[pattern.numberOfNames()];
@@ -353,7 +372,7 @@ public IRubyObject[] getNamedBackrefValues(Ruby runtime) {
             NameEntry e = i.next();
 
             int nth = pattern.nameToBackrefNumber(e.name, e.nameP, e.nameEnd, regs);
-            values[j++] = RubyRegexp.nth_match(nth, this);
+            values[j++] = RubyRegexp.nth_match(context, nth, this);
         }
 
         return values;
@@ -361,7 +380,7 @@ public IRubyObject[] getNamedBackrefValues(Ruby runtime) {
 
     @JRubyMethod
     public IRubyObject byteoffset(ThreadContext context, IRubyObject group) {
-        int index = backrefNumber(context.runtime, group);
+        int index = backrefNumber(context, group);
         Region regs = this.regs;
 
         backrefNumberCheck(context, index);
@@ -382,7 +401,7 @@ public RubyString inspect(ThreadContext context) {
 
         NameEntry[] names = new NameEntry[regs == null ? 1 : regs.getNumRegs()];
 
-        final Regex pattern = getPattern();
+        final Regex pattern = getPattern(context);
         for (Iterator<NameEntry> i = pattern.namedBackrefIterator(); i.hasNext();) {
             NameEntry e = i.next();
             for (int num : e.getBackRefs()) names[num] = e;
@@ -399,7 +418,7 @@ public RubyString inspect(ThreadContext context) {
                 }
                 result.cat((byte)':');
             }
-            IRubyObject v = RubyRegexp.nth_match(i, this);
+            IRubyObject v = RubyRegexp.nth_match(context, i, this);
             if (v.isNil()) {
                 result.cat(RubyNil.nilBytes); // "nil"
             } else {
@@ -412,14 +431,14 @@ public RubyString inspect(ThreadContext context) {
 
     @JRubyMethod
     public RubyRegexp regexp(ThreadContext context, Block block) {
-        check();
-        return getRegexp();
+        check(context);
+        return getRegexp(context);
     }
 
     @JRubyMethod
     public IRubyObject names(ThreadContext context, Block block) {
-        check();
-        return getRegexp().names(context);
+        check(context);
+        return getRegexp(context).names(context);
     }
 
     /** match_to_a
@@ -433,17 +452,17 @@ public RubyArray to_a(ThreadContext context) {
 
     @JRubyMethod(rest = true)
     public IRubyObject values_at(ThreadContext context, IRubyObject[] args) {
-        check();
+        check(context);
 
         var result = newRawArray(context, args.length);
 
         for (IRubyObject arg : args) {
-            if (arg instanceof RubyFixnum) {
-                result.append(context, RubyRegexp.nth_match(arg.convertToInteger().getIntValue(), this));
+            if (arg instanceof RubyFixnum fix) {
+                result.append(context, RubyRegexp.nth_match(context, fix.getIntValue(), this));
             } else {
                 int num = namevToBackrefNumber(context, arg);
                 if (num >= 0) {
-                    result.append(context, RubyRegexp.nth_match(num, this));
+                    result.append(context, RubyRegexp.nth_match(context, num, this));
                 } else {
                     matchAryAref(context, arg, result);
                 }
@@ -453,8 +472,9 @@ public IRubyObject values_at(ThreadContext context, IRubyObject[] args) {
         return result.finishRawArray(context);
     }
 
+    @Deprecated(since = "10.0")
     public IRubyObject values_at(IRubyObject[] args) {
-        return values_at(metaClass.runtime.getCurrentContext(), args);
+        return values_at(getCurrentContext(), args);
     }
 
     /** match_captures
@@ -465,22 +485,22 @@ public IRubyObject captures(ThreadContext context) {
         return match_array(context, 1);
     }
 
-    private int nameToBackrefNumber(RubyString str) {
-        check();
-        return nameToBackrefNumber(metaClass.runtime, getPattern(), regs, str);
+    private int nameToBackrefNumber(ThreadContext context, RubyString str) {
+        check(context);
+        return nameToBackrefNumber(context, getPattern(context), regs, str);
     }
 
-    private static int nameToBackrefNumber(Ruby runtime, Regex pattern, Region regs, ByteListHolder str) {
+    private static int nameToBackrefNumber(ThreadContext context, Regex pattern, Region regs, ByteListHolder str) {
         assert pattern != null;
         ByteList value = str.getByteList();
         try {
             return pattern.nameToBackrefNumber(value.getUnsafeBytes(), value.getBegin(), value.getBegin() + value.getRealSize(), regs);
         } catch (JOniException je) {
             if (je instanceof ValueException) {
-                throw runtime.newIndexError(str(runtime, "undefined group name reference: ", runtime.newString(value)));
+                throw context.runtime.newIndexError(str(context.runtime, "undefined group name reference: ", newString(context, value)));
             }
             // FIXME: I think we could only catch ValueException here, but someone needs to audit that.
-            throw runtime.newIndexError(je.getMessage());
+            throw context.runtime.newIndexError(je.getMessage());
         }
     }
 
@@ -492,16 +512,24 @@ private static int nameToBackrefNumber(Regex pattern, Region regs, ByteList name
         }
     }
 
+    @Deprecated(since = "10.0")
     public final int backrefNumber(Ruby runtime, IRubyObject obj) {
-        check();
-        return backrefNumber(runtime, getPattern(), regs, obj);
+        return backrefNumber(runtime.getCurrentContext(), obj);
     }
 
+    public final int backrefNumber(ThreadContext context, IRubyObject obj) {
+        check(context);
+        return backrefNumber(context, getPattern(context), regs, obj);
+    }
+
+    @Deprecated(since = "10.0")
     public static int backrefNumber(Ruby runtime, Regex pattern, Region regs, IRubyObject obj) {
-        if (obj instanceof RubySymbol sym) {
-            return nameToBackrefNumber(runtime, pattern, regs, (RubyString) sym.to_s(runtime.getCurrentContext()));
-        }
-        if (obj instanceof RubyString str) return nameToBackrefNumber(runtime, pattern, regs, str);
+        return backrefNumber(runtime.getCurrentContext(), pattern, regs, obj);
+    }
+
+    public static int backrefNumber(ThreadContext context, Regex pattern, Region regs, IRubyObject obj) {
+        if (obj instanceof RubySymbol sym) return nameToBackrefNumber(context, pattern, regs, (RubyString) sym.to_s(context));
+        if (obj instanceof RubyString str) return nameToBackrefNumber(context, pattern, regs, str);
         return RubyNumeric.num2int(obj);
     }
 
@@ -516,8 +544,8 @@ private int namevToBackrefNumber(ThreadContext context, IRubyObject name) {
             case STRING:
                 Ruby runtime = context.runtime;
                 if (regexp.isNil() || RubyEncoding.areCompatible(regexp, name) == null ||
-                        (num = nameToBackrefNumber(runtime, regexp.getPattern(), regs, name.convertToString())) < 1) {
-                    nameToBackrefError(runtime, name.toString());
+                        (num = nameToBackrefNumber(context, regexp.getPattern(context), regs, name.convertToString())) < 1) {
+                    nameToBackrefError(context, name.toString());
                 }
                 return num;
 
@@ -526,8 +554,8 @@ private int namevToBackrefNumber(ThreadContext context, IRubyObject name) {
         }
     }
 
-    private int nameToBackrefError(Ruby runtime, String name) {
-        throw runtime.newIndexError("undefined group name reference " + name);
+    private int nameToBackrefError(ThreadContext context, String name) {
+        throw context.runtime.newIndexError("undefined group name reference " + name);
     }
 
     // MRI: match_ary_subseq
@@ -541,7 +569,7 @@ private IRubyObject matchArySubseq(ThreadContext context, int beg, int len, Ruby
         if (len == 0) return result;
 
         for (j = beg; j < end; j++) {
-            result.append(context, RubyRegexp.nth_match(j, this));
+            result.append(context, RubyRegexp.nth_match(context, j, this));
         }
 
         // if not enough groups, force length to be as wide as desired by setting last value to nil
@@ -564,7 +592,7 @@ private IRubyObject matchAryAref(ThreadContext context, IRubyObject index, RubyA
         if (isRange.isNil()) return context.nil;
 
         if (!isRange.isTrue()) {
-            IRubyObject nthMatch = RubyRegexp.nth_match(index.convertToInteger().getIntValue(), this);
+            IRubyObject nthMatch = RubyRegexp.nth_match(context, index.convertToInteger().getIntValue(), this);
 
             // this should never happen here, but MRI allows any VALUE for result
             // if (result.isNil()) return nthMatch;
@@ -580,7 +608,7 @@ private IRubyObject matchAryAref(ThreadContext context, IRubyObject index, RubyA
      */
     @JRubyMethod(name = "[]")
     public IRubyObject op_aref(ThreadContext context, IRubyObject idx) {
-        check();
+        check(context);
         IRubyObject result = op_arefCommon(context, idx);
         return result == null ? to_a(context).aref(context, idx) : result;
     }
@@ -598,20 +626,22 @@ public IRubyObject op_aref(ThreadContext context, IRubyObject idx, IRubyObject r
     private IRubyObject op_arefCommon(ThreadContext context, IRubyObject idx) {
         if (idx instanceof RubyFixnum) {
             int num = RubyNumeric.fix2int(idx);
-            if (num >= 0) return RubyRegexp.nth_match(num, this);
-        } else {
-            if (idx instanceof RubySymbol) {
-                return RubyRegexp.nth_match(nameToBackrefNumber((RubyString) ((RubySymbol) idx).to_s(context)), this);
-            }
-            if (idx instanceof RubyString) {
-                return RubyRegexp.nth_match(nameToBackrefNumber((RubyString) idx), this);
-            }
+            if (num >= 0) return RubyRegexp.nth_match(context, num, this);
+        } else if (idx instanceof RubySymbol index) {
+            return RubyRegexp.nth_match(context, nameToBackrefNumber(context, (RubyString) index.to_s(context)), this);
+        } else if (idx instanceof RubyString index) {
+            return RubyRegexp.nth_match(context, nameToBackrefNumber(context, index), this);
         }
         return null;
     }
 
+    @Deprecated(since = "10.0")
     public final IRubyObject at(final int nth) {
-        return RubyRegexp.nth_match(nth, this);
+        return at(getCurrentContext(), nth);
+    }
+
+    public final IRubyObject at(ThreadContext context, final int nth) {
+        return RubyRegexp.nth_match(context, nth, this);
     }
 
     /** match_size
@@ -619,7 +649,7 @@ public final IRubyObject at(final int nth) {
      */
     @JRubyMethod(name = {"size", "length"})
     public IRubyObject size(ThreadContext context) {
-        check();
+        check(context);
         return regs == null ? RubyFixnum.one(context.runtime) : asFixnum(context, regs.getNumRegs());
     }
 
@@ -628,8 +658,8 @@ public IRubyObject size(ThreadContext context) {
      */
     @JRubyMethod
     public IRubyObject begin(ThreadContext context, IRubyObject index) {
-        check();
-        final int i = backrefNumber(context.runtime, index);
+        check(context);
+        final int i = backrefNumber(context, index);
 
         backrefNumberCheck(context, i);
 
@@ -646,9 +676,9 @@ public IRubyObject begin(ThreadContext context, IRubyObject index) {
      */
     @JRubyMethod
     public IRubyObject end(ThreadContext context, IRubyObject index) {
-        check();
+        check(context);
 
-        final int i = backrefNumber(context.runtime, index);
+        final int i = backrefNumber(context, index);
 
         backrefNumberCheck(context, i);
 
@@ -673,9 +703,9 @@ public IRubyObject offset19(ThreadContext context, IRubyObject index) {
      */
     @JRubyMethod(name = "offset")
     public IRubyObject offset(ThreadContext context, IRubyObject index) {
-        check();
+        check(context);
 
-        final int i = backrefNumber(context.runtime, index);
+        final int i = backrefNumber(context, index);
         backrefNumberCheck(context, i);
 
         int b, e;
@@ -703,10 +733,8 @@ public IRubyObject offset(ThreadContext context, IRubyObject index) {
      */
     @JRubyMethod
     public IRubyObject pre_match(ThreadContext context) {
-        check();
-        if (begin == -1) return context.nil;
-
-        return str.makeSharedString(context.runtime, 0, begin);
+        check(context);
+        return begin == -1 ? context.nil : str.makeSharedString(context.runtime, 0, begin);
     }
 
     @JRubyMethod
@@ -768,11 +796,10 @@ private void backrefNumberCheck(ThreadContext context, int i) {
      */
     @JRubyMethod
     public IRubyObject post_match(ThreadContext context) {
-        check();
-        if (begin == -1) return context.nil;
+        check(context);
 
-        final int strLen = str.getByteList().length();
-        return str.makeSharedString(context.runtime, end, strLen - end);
+        return begin == -1 ?
+                context.nil : str.makeSharedString(context.runtime, end, str.getByteList().length() - end);
     }
 
     /** match_to_s
@@ -781,17 +808,21 @@ public IRubyObject post_match(ThreadContext context) {
     @JRubyMethod
     @Override
     public IRubyObject to_s(ThreadContext context) {
-        check();
+        check(context);
         IRubyObject ss = RubyRegexp.last_match(this);
         return ss.isNil() ? newEmptyString(context) : ss;
     }
 
+    @Deprecated(since = "10.0")
+    public IRubyObject string() {
+        return string(getCurrentContext());
+    }
     /** match_string
      *
      */
     @JRubyMethod
-    public IRubyObject string() {
-        check();
+    public IRubyObject string(ThreadContext context) {
+        check(context);
         return str; //str is frozen
     }
 
@@ -813,8 +844,10 @@ public boolean equals(Object other) {
         if (this == other) return true;
         if (!(other instanceof RubyMatchData that)) return false;
 
+        var context = getRuntime().getCurrentContext();
+
         return (this.str == that.str || (this.str != null && this.str.equals(that.str))) &&
-               (this.regexp == that.regexp || (this.getRegexp().equals(that.getRegexp()))) &&
+               (this.regexp == that.regexp || (this.getRegexp(context).equals(that.getRegexp(context)))) &&
                (this.charOffsets == that.charOffsets || (this.charOffsets != null && this.charOffsets.equals(that.charOffsets))) &&
                this.charOffsetUpdated == that.charOffsetUpdated &&
                this.begin == that.begin && this.end == that.end;
@@ -827,8 +860,9 @@ public IRubyObject eql_p(ThreadContext context, IRubyObject obj) {
 
     @Override
     public int hashCode() {
-        check();
-        return getPattern().hashCode() ^ str.hashCode();
+        var context = getRuntime().getCurrentContext();
+        check(context);
+        return getPattern(context).hashCode() ^ str.hashCode();
     }
 
     @JRubyMethod
@@ -838,7 +872,7 @@ public RubyFixnum hash(ThreadContext context) {
 
     @JRubyMethod(keywords = true, optional = 1)
     public RubyHash named_captures(ThreadContext context, IRubyObject[] args) {
-        check();
+        check(context);
 
         int argc = Arity.checkArgumentCount(context, args.length, 0, 0, true);
         RubyHash hash = newSmallHash(context);
@@ -846,8 +880,8 @@ public RubyHash named_captures(ThreadContext context, IRubyObject[] args) {
 
         final boolean symbolizeNames;
         if (argc == 1) {
-            if (!(args[0] instanceof RubyHash)) throw argumentError(context, 1, 0);
-            IRubyObject value = ArgsUtil.extractKeywordArg(context, (RubyHash) args[0], "symbolize_names");
+            if (!(args[0] instanceof RubyHash opts)) throw argumentError(context, 1, 0);
+            IRubyObject value = ArgsUtil.extractKeywordArg(context, opts, "symbolize_names");
             symbolizeNames = value != null && value.isTrue();
         } else {
             symbolizeNames = false;
@@ -858,7 +892,7 @@ public RubyHash named_captures(ThreadContext context, IRubyObject[] args) {
             boolean found = false;
 
             for (int b : entry.getBackRefs()) {
-                IRubyObject value = RubyRegexp.nth_match(b, this);
+                IRubyObject value = RubyRegexp.nth_match(context, b, this);
 
                 if (value.isTrue()) {
                     hash.op_aset(context, key, value);
@@ -886,12 +920,12 @@ public IRubyObject deconstruct_keys(ThreadContext context, IRubyObject what) {
                 RubySymbol key = symbolFromNameEntry(context, entry);
 
                 for (int b : entry.getBackRefs()) {
-                    IRubyObject value = RubyRegexp.nth_match(b, this);
+                    IRubyObject value = RubyRegexp.nth_match(context, b, this);
                     if (value.isTrue()) hash.op_aset(context, key, value);
                 }
             });
         } else if (what instanceof RubyArray arr) {
-            if (getPattern().numberOfNames() < arr.size()) return hash;
+            if (getPattern(context).numberOfNames() < arr.size()) return hash;
 
             Iterable<IRubyObject> iterable = () -> arr.rubyStream().iterator();
             for (IRubyObject obj : iterable) {
@@ -899,10 +933,10 @@ public IRubyObject deconstruct_keys(ThreadContext context, IRubyObject what) {
                     throw typeError(context, str(context.runtime, "wrong argument type ", obj.getMetaClass(), " (expected Symbol)"));
                 }
 
-                int index = nameToBackrefNumber(getPattern(), regs, requestedKey.getBytes());
+                int index = nameToBackrefNumber(getPattern(context), regs, requestedKey.getBytes());
                 if (index == -1) break;
 
-                IRubyObject value = RubyRegexp.nth_match(index, this);
+                IRubyObject value = RubyRegexp.nth_match(context, index, this);
                 if (!value.isTrue()) break;
 
                 hash.op_aset(context, requestedKey, value);
@@ -914,7 +948,7 @@ public IRubyObject deconstruct_keys(ThreadContext context, IRubyObject what) {
     }
 
     private Stream<NameEntry> getNamedBackrefKeys(ThreadContext context) {
-        Iterable<NameEntry> iterable = () -> getPattern().namedBackrefIterator();
+        Iterable<NameEntry> iterable = () -> getPattern(context).namedBackrefIterator();
         return StreamSupport.stream(iterable.spliterator(), false);
     }
 
@@ -972,17 +1006,17 @@ public int numRegs() {
     @Deprecated
     @Override
     public RubyArray to_a() {
-        return match_array(getRuntime().getCurrentContext(), 0);
+        return match_array(getCurrentContext(), 0);
     }
 
     @Deprecated
     public IRubyObject op_aref(IRubyObject idx) {
-        return op_aref(getRuntime().getCurrentContext(), idx);
+        return op_aref(getCurrentContext(), idx);
     }
 
     @Deprecated
     public IRubyObject op_aref(IRubyObject idx, IRubyObject rest) {
-        return op_aref(getRuntime().getCurrentContext(), idx, rest);
+        return op_aref(getCurrentContext(), idx, rest);
     }
 
 }
diff --git a/core/src/main/java/org/jruby/RubyRational.java b/core/src/main/java/org/jruby/RubyRational.java
index f61da07a417..0725478dc66 100644
--- a/core/src/main/java/org/jruby/RubyRational.java
+++ b/core/src/main/java/org/jruby/RubyRational.java
@@ -1422,9 +1422,9 @@ static IRubyObject[] str_to_r_internal(final ThreadContext context, final RubySt
         }
         if (m != nil) {
             RubyMatchData match = (RubyMatchData) m;
-            IRubyObject si = match.at(1);
-            RubyString nu = (RubyString) match.at(2);
-            IRubyObject de = match.at(3);
+            IRubyObject si = match.at(context, 1);
+            RubyString nu = (RubyString) match.at(context, 2);
+            IRubyObject de = match.at(context, 3);
             IRubyObject re = match.post_match(context);
             
             var a = nu.split(context, RubyRegexp.newDummyRegexp(context.runtime, Numeric.RationalPatterns.an_e_pat));
diff --git a/core/src/main/java/org/jruby/RubyRegexp.java b/core/src/main/java/org/jruby/RubyRegexp.java
index 2e2ca4ea47a..632bdf7f4e2 100755
--- a/core/src/main/java/org/jruby/RubyRegexp.java
+++ b/core/src/main/java/org/jruby/RubyRegexp.java
@@ -37,10 +37,6 @@
 
 package org.jruby;
 
-import static org.jruby.RubyNumeric.fix2int;
-import static org.jruby.anno.FrameField.BACKREF;
-import static org.jruby.anno.FrameField.LASTLINE;
-
 import org.jcodings.Encoding;
 import org.jcodings.specific.ASCIIEncoding;
 import org.jcodings.specific.USASCIIEncoding;
@@ -56,7 +52,6 @@
 import org.jruby.anno.JRubyClass;
 import org.jruby.anno.JRubyMethod;
 import org.jruby.api.Convert;
-import org.jruby.common.IRubyWarnings.ID;
 import org.jruby.exceptions.RaiseException;
 import org.jruby.parser.ReOptions;
 import org.jruby.runtime.Block;
@@ -76,14 +71,27 @@
 import org.jruby.util.StringSupport;
 import org.jruby.util.TypeConverter;
 import org.jruby.util.cli.Options;
-import org.jruby.util.io.EncodingUtils;
 import org.jruby.util.collections.WeakValuedMap;
+import org.jruby.util.io.EncodingUtils;
+
+import java.util.Iterator;
 
+import static org.jruby.RubyNumeric.fix2int;
+import static org.jruby.anno.FrameField.BACKREF;
+import static org.jruby.anno.FrameField.LASTLINE;
 import static org.jruby.api.Access.instanceConfig;
-import static org.jruby.api.Convert.*;
-import static org.jruby.api.Create.*;
+import static org.jruby.api.Convert.asBoolean;
+import static org.jruby.api.Convert.asFixnum;
+import static org.jruby.api.Convert.asFloat;
+import static org.jruby.api.Convert.asSymbol;
+import static org.jruby.api.Create.dupString;
+import static org.jruby.api.Create.newEmptyArray;
+import static org.jruby.api.Create.newHash;
+import static org.jruby.api.Create.newString;
 import static org.jruby.api.Define.defineClass;
-import static org.jruby.api.Error.*;
+import static org.jruby.api.Error.argumentError;
+import static org.jruby.api.Error.runtimeError;
+import static org.jruby.api.Error.typeError;
 import static org.jruby.api.Warn.warn;
 import static org.jruby.api.Warn.warning;
 import static org.jruby.runtime.ThreadContext.resetCallInfo;
@@ -91,8 +99,6 @@
 import static org.jruby.util.StringSupport.CR_7BIT;
 import static org.jruby.util.StringSupport.EMPTY_STRING_ARRAY;
 
-import java.util.Iterator;
-
 @JRubyClass(name="Regexp")
 public class RubyRegexp extends RubyObject implements ReOptions, EncodingCapable, MarshalEncoding {
     Regex pattern;
@@ -184,13 +190,13 @@ public static Regex getRegexpFromCache(Ruby runtime, ByteList bytes, Encoding en
         return regex;
     }
 
-    static Regex getQuotedRegexpFromCache(Ruby runtime, RubyString str, RegexpOptions options) {
+    static Regex getQuotedRegexpFromCache(ThreadContext context, RubyString str, RegexpOptions options) {
         final ByteList bytes = str.getByteList();
         Regex regex = quotedPatternCache.get(bytes);
         Encoding enc = str.isAsciiOnly() ? USASCIIEncoding.INSTANCE : bytes.getEncoding();
         if (regex != null && regex.getEncoding() == enc && regex.getOptions() == options.toJoniOptions()) return regex;
         final ByteList quoted = quote(str);
-        regex = makeRegexp(runtime, quoted, options, quoted.getEncoding());
+        regex = makeRegexp(context.runtime, quoted, options, quoted.getEncoding());
         regex.setUserObject(quoted);
         quotedPatternCache.put(bytes, regex);
         return regex;
@@ -376,26 +382,36 @@ public static RubyRegexp newRegexpFromStr(Ruby runtime, RubyString s, int option
         return re;
     }
 
+    @Deprecated(since = "10.0")
+    public final RegexpOptions getOptions() {
+        return getOptions(getCurrentContext());
+    }
+
     /** rb_reg_options
      */
-    public final RegexpOptions getOptions() {
-        check();
+    public final RegexpOptions getOptions(ThreadContext context) {
+        check(context);
         return options;
     }
 
+    @Deprecated(since = "10.0")
     public final Regex getPattern() {
-        check();
+        return getPattern(getCurrentContext());
+    }
+
+    public final Regex getPattern(ThreadContext context) {
+        check(context);
         return pattern;
     }
 
-    final Encoding checkEncoding(RubyString other) {
+    Encoding checkEncoding(ThreadContext context, RubyString other) {
         Encoding enc = other.isCompatibleWith(this);
-        if (enc == null) encodingMatchError(getRuntime(), pattern, other.getEncoding());
+        if (enc == null) encodingMatchError(context, pattern, other.getEncoding());
         return enc;
     }
 
-    private static void encodingMatchError(Ruby runtime, Regex pattern, Encoding strEnc) {
-        throw runtime.newEncodingCompatibilityError("incompatible encoding regexp match (" +
+    private static void encodingMatchError(ThreadContext context, Regex pattern, Encoding strEnc) {
+        throw context.runtime.newEncodingCompatibilityError("incompatible encoding regexp match (" +
                 pattern.getEncoding() + " regexp with " + strEnc + " string)");
     }
 
@@ -404,17 +420,17 @@ private Encoding prepareEncoding(ThreadContext context, RubyString str, boolean
         int cr = str.scanForCodeRange();
         if (cr == StringSupport.CR_BROKEN) throw argumentError(context, "invalid byte sequence in " + enc);
 
-        check();
+        check(context);
         Encoding patternEnc = pattern.getEncoding();
         if (patternEnc == enc) {
         } else if (cr == StringSupport.CR_7BIT && patternEnc == USASCIIEncoding.INSTANCE) {
             enc = patternEnc;
         } else if (!enc.isAsciiCompatible()) {
-            encodingMatchError(getRuntime(), pattern, enc);
+            encodingMatchError(context, pattern, enc);
         } else if (options.isFixed()) {
             if (enc != patternEnc &&
                (!patternEnc.isAsciiCompatible() ||
-               cr != StringSupport.CR_7BIT)) encodingMatchError(getRuntime(), pattern, enc);
+               cr != StringSupport.CR_7BIT)) encodingMatchError(context, pattern, enc);
             enc = patternEnc;
         }
         if (warn && isEncodingNone() && enc != ASCIIEncoding.INSTANCE && cr != StringSupport.CR_7BIT) {
@@ -630,8 +646,8 @@ private static Encoding processDRegexpElement(ThreadContext context, RegexpOptio
         return regexpEnc;
     }
 
-    private void check() {
-        if (pattern == null) throw typeError(getRuntime().getCurrentContext(),"uninitialized Regexp");
+    private void check(ThreadContext context) {
+        if (pattern == null) throw typeError(context, "uninitialized Regexp");
     }
 
     @JRubyMethod(meta = true)
@@ -781,12 +797,9 @@ public static IRubyObject last_match_s(ThreadContext context, IRubyObject recv)
     */
     @JRubyMethod(name = "last_match", meta = true, reads = BACKREF)
     public static IRubyObject last_match_s(ThreadContext context, IRubyObject recv, IRubyObject nth) {
-        IRubyObject backref = context.getBackRef();
-        if (backref instanceof RubyMatchData) {
-            RubyMatchData match = ((RubyMatchData) backref);
-            return nth_match(match.backrefNumber(context.runtime, nth), match);
-        }
-        return backref; // nil
+        return context.getBackRef() instanceof RubyMatchData match ?
+                nth_match(context, match.backrefNumber(context, nth), match) :
+                context.nil;
     }
 
     /** rb_reg_s_union
@@ -829,7 +842,7 @@ public static IRubyObject union(ThreadContext context, IRubyObject recv, IRubyOb
                         } else if (hasAsciiIncompat != enc) { // n kcode doesn't match first one
                             throw argumentError(context, "incompatible encodings: " + hasAsciiIncompat + " and " + enc);
                         }
-                    } else if (regex.getOptions().isFixed()) {
+                    } else if (regex.getOptions(context).isFixed()) {
                         if (hasAsciiCompatFixed == null) { // First regexp of union sets kcode.
                             hasAsciiCompatFixed = enc;
                         } else if (hasAsciiCompatFixed != enc) { // n kcode doesn't match first one
@@ -897,23 +910,18 @@ public IRubyObject initialize_copy(ThreadContext context, IRubyObject re) {
         }
 
         RubyRegexp regexp = (RubyRegexp)re;
-        regexp.check();
+        regexp.check(context);
 
-        return regexpInitialize(regexp.str, regexp.str.getEncoding(), regexp.getOptions(), regexp.timeout);
+        return regexpInitialize(regexp.str, regexp.str.getEncoding(), regexp.getOptions(context), regexp.timeout);
     }
 
     private static int objectAsJoniOptions(ThreadContext context, IRubyObject arg) {
-        Ruby runtime = arg.getRuntime();
         if (arg instanceof RubyFixnum) return fix2int(arg);
-        if (arg instanceof RubyString) return RegexpOptions.fromByteList(runtime, ((RubyString) arg).getByteList()).toJoniOptions();
-        if (arg instanceof RubyBoolean) {
-            if (arg.isTrue()) return RE_OPTION_IGNORECASE;
-
-            return 0;
-        }
+        if (arg instanceof RubyString str) return RegexpOptions.fromByteList(context, str.getByteList()).toJoniOptions();
+        if (arg instanceof RubyBoolean) return arg.isTrue() ? RE_OPTION_IGNORECASE : 0;
         if (arg.isNil()) return 0;
 
-        warning(context, str(runtime, "expected true or false as ignorecase: ", arg));
+        warning(context, str(context.runtime, "expected true or false as ignorecase: ", arg));
 
         return RE_OPTION_IGNORECASE;
     }
@@ -926,7 +934,7 @@ public IRubyObject initialize_m(IRubyObject arg) {
     @JRubyMethod(name = "initialize", visibility = Visibility.PRIVATE)
     public IRubyObject initialize_m(ThreadContext context, IRubyObject arg) {
         return arg instanceof RubyRegexp regexp ?
-                initializeByRegexp(regexp, null) :
+                initializeByRegexp(context, regexp, null) :
                 regexpInitializeString(context, arg.convertToString(), new RegexpOptions(), null);
     }
 
@@ -944,11 +952,11 @@ public IRubyObject initialize_m(ThreadContext context, IRubyObject arg0, IRubyOb
         if (keywords) {
             regexpOptions = new RegexpOptions();
             timeout = timeoutFromArg(context, arg1);
-            if (arg0 instanceof RubyRegexp regexp) return initializeByRegexp(regexp, timeout);
+            if (arg0 instanceof RubyRegexp regexp) return initializeByRegexp(context, regexp, timeout);
         } else {
             if (arg0 instanceof RubyRegexp && Options.PARSER_WARN_FLAGS_IGNORED.load()) {
                 warn(context, "flags ignored");
-                return initializeByRegexp((RubyRegexp)arg0, null);
+                return initializeByRegexp(context, (RubyRegexp)arg0, null);
             }
             regexpOptions = RegexpOptions.fromJoniOptions(objectAsJoniOptions(context, arg1));
             timeout = null;
@@ -975,7 +983,7 @@ public IRubyObject initialize_m(ThreadContext context, IRubyObject arg0, IRubyOb
 
         if (arg0 instanceof RubyRegexp && Options.PARSER_WARN_FLAGS_IGNORED.load()) {
             warn(context, "flags ignored");
-            return initializeByRegexp((RubyRegexp)arg0, timeoutFromArg(context, arg2));
+            return initializeByRegexp(context, (RubyRegexp)arg0, timeoutFromArg(context, arg2));
         }
 
         RegexpOptions newOptions = RegexpOptions.fromJoniOptions(objectAsJoniOptions(context, arg1));
@@ -988,10 +996,10 @@ private IRubyObject timeoutFromArg(ThreadContext context, IRubyObject arg) {
         return Convert.castAsHash(context, arg).fastARef(asSymbol(context, "timeout"));
     }
 
-    private IRubyObject initializeByRegexp(RubyRegexp regexp, IRubyObject timeoutProvided) {
+    private IRubyObject initializeByRegexp(ThreadContext context, RubyRegexp regexp, IRubyObject timeoutProvided) {
         // Clone and toggle flags since this is no longer a literal regular expression
         // but it did come from one.
-        RegexpOptions newOptions = regexp.getOptions().clone();
+        RegexpOptions newOptions = regexp.getOptions(context).clone();
         newOptions.setLiteral(false);
         return regexpInitialize(regexp.str, regexp.getEncoding(), newOptions, timeoutProvided != null ? timeoutProvided : regexp.timeout);
     }
@@ -1054,7 +1062,7 @@ public final RubyRegexp regexpInitialize(ByteList bytes, Encoding enc, RegexpOpt
 
     @JRubyMethod
     public RubyFixnum hash(ThreadContext context) {
-        check();
+        check(context);
         int hash = pattern.getOptions();
         int len = str.getRealSize();
         int p = str.getBegin();
@@ -1069,12 +1077,10 @@ public RubyFixnum hash(ThreadContext context) {
     @Override
     public IRubyObject op_equal(ThreadContext context, IRubyObject other) {
         if (this == other) return context.tru;
-        if (!(other instanceof RubyRegexp)) return context.fals;
+        if (!(other instanceof RubyRegexp otherRegex)) return context.fals;
 
-        RubyRegexp otherRegex = (RubyRegexp) other;
-
-        check();
-        otherRegex.check();
+        check(context);
+        otherRegex.check(context);
 
         return asBoolean(context, str.equal(otherRegex.str) && options.equals(otherRegex.options));
     }
@@ -1394,7 +1400,7 @@ static RubyMatchData createMatchData(ThreadContext context, RubyString str, int
 
     @JRubyMethod
     public IRubyObject options(ThreadContext context) {
-        return asFixnum(context, getOptions().toOptions());
+        return asFixnum(context, getOptions(context).toOptions());
     }
 
     @Deprecated
@@ -1404,7 +1410,7 @@ public IRubyObject options() {
 
     @JRubyMethod(name = "casefold?")
     public IRubyObject casefold_p(ThreadContext context) {
-        return asBoolean(context, getOptions().isIgnorecase());
+        return asBoolean(context, getOptions(context).isIgnorecase());
     }
 
     /** rb_reg_source
@@ -1412,7 +1418,7 @@ public IRubyObject casefold_p(ThreadContext context) {
      */
     @JRubyMethod
     public IRubyObject source(ThreadContext context) {
-        check();
+        check(context);
         var enc = pattern == null ? str.getEncoding() : pattern.getEncoding();
         ByteList newStr = str.dup();
         newStr.setEncoding(enc);
@@ -1448,7 +1454,7 @@ public IRubyObject inspect(ThreadContext context) {
     @Override
     @JRubyMethod
     public RubyString to_s(ThreadContext context) {
-        check();
+        check(context);
 
         RegexpOptions newOptions = options.clone();
         int p = str.getBegin();
@@ -1555,7 +1561,7 @@ public String[] getNames() {
      */
     @JRubyMethod
     public IRubyObject names(ThreadContext context) {
-        check();
+        check(context);
 
         if (pattern.numberOfNames() == 0) return newEmptyArray(context);
 
@@ -1574,7 +1580,7 @@ public IRubyObject names(ThreadContext context) {
      */
     @JRubyMethod
     public IRubyObject named_captures(ThreadContext context) {
-        check();
+        check(context);
         RubyHash hash = newHash(context);
         if (pattern.numberOfNames() == 0) return hash;
 
@@ -1643,83 +1649,106 @@ public static IRubyObject linear_time_p(ThreadContext context, IRubyObject recv,
         return pattern != null && pattern.isLinear() ? context.tru : context.fals;
     }
 
+    @Deprecated(since = "10.0")
+    public static IRubyObject nth_match(int nth, IRubyObject match) {
+        return nth_match(((RubyBasicObject) match).getCurrentContext(), nth, match);
+    }
+
     /** rb_reg_nth_match
     *
     */
-    public static IRubyObject nth_match(int nth, IRubyObject match) {
-        if (match.isNil()) return match;
-        return nth_match(nth, (RubyMatchData) match);
+    public static IRubyObject nth_match(ThreadContext context, int nth, IRubyObject matchArg) {
+        return matchArg instanceof RubyMatchData match ?
+                nth_match(context, nth, match) : context.nil;
     }
 
-    static IRubyObject nth_match(int nth, RubyMatchData match) {
-        match.check();
+    static IRubyObject nth_match(ThreadContext context, int nth, RubyMatchData match) {
+        match.check(context);
 
         final int start, end;
         if (match.regs == null) {
-            if (nth >= 1 || (nth < 0 && ++nth <= 0)) return match.getRuntime().getNil();
+            if (nth >= 1 || (nth < 0 && ++nth <= 0)) return context.nil;
             start = match.begin;
             end = match.end;
         } else {
             if (nth >= match.regs.getNumRegs() || (nth < 0 && (nth+=match.regs.getNumRegs()) <= 0)) {
-                return match.getRuntime().getNil();
+                return context.nil;
             }
             start = match.regs.getBeg(nth);
             end = match.regs.getEnd(nth);
         }
 
-        if (start == -1) return match.getRuntime().getNil();
+        return start == -1 ?
+                context.nil : match.str.makeSharedString(context.runtime, start, end - start);
+    }
 
-        return match.str.makeSharedString(match.metaClass.runtime, start, end - start);
+    @Deprecated(since = "10.0")
+    public static IRubyObject last_match(IRubyObject match) {
+        return last_match(((RubyBasicObject) match).getCurrentContext(), match);
     }
 
     /** rb_reg_last_match
      *
      */
-    public static IRubyObject last_match(IRubyObject match) {
-        return nth_match(0, match);
+    public static IRubyObject last_match(ThreadContext context, IRubyObject match) {
+        return nth_match(context, 0, match);
+    }
+
+
+    @Deprecated(since = "10.0")
+    public static IRubyObject match_pre(IRubyObject match) {
+        return match_pre(((RubyBasicObject) match).getCurrentContext(), match);
     }
 
     /** rb_reg_match_pre
      *
      */
-    public static IRubyObject match_pre(IRubyObject match) {
-        if (match.isNil()) return match;
-        RubyMatchData m = (RubyMatchData)match;
-        m.check();
+    public static IRubyObject match_pre(ThreadContext context, IRubyObject matchArg) {
+        if (!(matchArg instanceof RubyMatchData match)) return context.nil;
+
+        match.check(context);
+
+        return match.begin == -1 ?
+                context.nil : match.str.makeShared(context.runtime, 0,  match.begin);
+    }
 
-        Ruby runtime = m.getRuntime();
-        if (m.begin == -1) return runtime.getNil();
-        return m.str.makeShared(runtime, 0,  m.begin);
+    @Deprecated(since = "10.0")
+    public static IRubyObject match_post(IRubyObject match) {
+        return match_post(((RubyBasicObject) match).getCurrentContext(), match);
     }
 
     /** rb_reg_match_post
      *
      */
-    public static IRubyObject match_post(IRubyObject match) {
-        if (match.isNil()) return match;
-        RubyMatchData m = (RubyMatchData)match;
-        m.check();
+    public static IRubyObject match_post(ThreadContext context, IRubyObject matchArg) {
+        if (!(matchArg instanceof RubyMatchData match)) return context.nil;
+
+        match.check(context);
 
-        Ruby runtime = m.getRuntime();
-        if (m.begin == -1) return runtime.getNil();
-        return m.str.makeShared(runtime, m.end, m.str.getByteList().getRealSize() - m.end);
+        return match.begin != -1 ?
+                match.str.makeShared(context.runtime, match.end, match.str.getByteList().getRealSize() - match.end) :
+                context.nil;
+    }
+
+    @Deprecated(since = "10.0")
+    public static IRubyObject match_last(IRubyObject match) {
+        return match_last(((RubyBasicObject) match).getCurrentContext(), match);
     }
 
     /** rb_reg_match_last
      *
      */
-    public static IRubyObject match_last(IRubyObject match) {
-        if (match.isNil()) return match;
-        RubyMatchData m = (RubyMatchData) match;
-        m.check();
+    public static IRubyObject match_last(ThreadContext context, IRubyObject matchArg) {
+        if (!(matchArg instanceof RubyMatchData match)) return matchArg;
 
-        if (m.regs == null || m.regs.getBeg(0) == -1) return m.getRuntime().getNil();
+        match.check(context);
+
+        if (match.regs == null || match.regs.getBeg(0) == -1) return context.nil;
 
         int i;
-        for (i = m.regs.getNumRegs() - 1; m.regs.getBeg(i) == -1 && i > 0; i--);
-        if (i == 0) return m.getRuntime().getNil();
+        for (i = match.regs.getNumRegs() - 1; match.regs.getBeg(i) == -1 && i > 0; i--);
 
-        return nth_match(i, m);
+        return i == 0 ? context.nil : nth_match(context, i, match);
     }
 
     // MRI: ASCGET macro from rb_reg_regsub
@@ -1852,8 +1881,8 @@ static RubyString regsub(ThreadContext context, RubyString str, RubyString src,
         return val;
     }
 
-    final int adjustStartPos(RubyString str, int pos, boolean reverse) {
-        check();
+    final int adjustStartPos(ThreadContext context, RubyString str, int pos, boolean reverse) {
+        check(context);
         return adjustStartPosInternal(str, pattern.getEncoding(), pos, reverse);
     }
 
@@ -1897,7 +1926,7 @@ public static void marshalTo(RubyRegexp regexp, MarshalStream output) throws jav
 
         int options = regexp.pattern.getOptions() & EMBEDDABLE;
 
-        if (regexp.getOptions().isFixed()) options |= RE_FIXED;
+        if (regexp.getOptions(regexp.getRuntime().getCurrentContext()).isFixed()) options |= RE_FIXED;
 
         output.writeByte(options);
     }
@@ -1908,7 +1937,7 @@ public static void marshalTo(RubyRegexp regexp, NewMarshal output, NewMarshal.Ru
 
         int options = regexp.pattern.getOptions() & EMBEDDABLE;
 
-        if (regexp.getOptions().isFixed()) options |= RE_FIXED;
+        if (regexp.getOptions(regexp.getRuntime().getCurrentContext()).isFixed()) options |= RE_FIXED;
 
         output.writeByte(out, options);
     }
@@ -1929,16 +1958,20 @@ public static IRubyObject getBackRef(ThreadContext context) {
         return context.getBackRef();
     }
 
+    @Deprecated(since = "10.0")
+    public boolean isSimpleString() {
+        return isSimpleString(getCurrentContext());
+    }
     /**
      * Is the pattern itself a simple US-ASCII string which can be used in simple string searches and
      * can be used outside of the regexp engine?
      *
      */
-    public boolean isSimpleString() {
+    public boolean isSimpleString(ThreadContext context) {
         return isLiteral() &&
                 getEncoding().isAsciiCompatible() &&
                 RubyString.scanForCodeRange(str) == CR_7BIT &&
-                !getOptions().isIgnorecase() &&
+                !getOptions(context).isIgnorecase() &&
                 ((str.realSize() == 1 &&
                         str.charAt(0) != '.' &&
                         str.charAt(0) != '^' &&
diff --git a/core/src/main/java/org/jruby/RubyString.java b/core/src/main/java/org/jruby/RubyString.java
index 3b63fe264e5..90460f1f7f3 100644
--- a/core/src/main/java/org/jruby/RubyString.java
+++ b/core/src/main/java/org/jruby/RubyString.java
@@ -3018,7 +3018,7 @@ private IRubyObject subBangIter(ThreadContext context, RubyString pattern, RubyH
     }
 
     private IRubyObject subBangIter(ThreadContext context, RubyRegexp regexp, RubyHash hash, Block block) {
-        Regex pattern = regexp.getPattern();
+        Regex pattern = regexp.getPattern(context);
         Regex prepared = regexp.preparePattern(context, this);
 
         int begin = value.getBegin();
@@ -3118,7 +3118,7 @@ public final IRubyObject subBangFast(ThreadContext context, RubyRegexp regexp, R
     }
 
     private RubyMatchData subBangMatch(ThreadContext context, RubyRegexp regexp, RubyString repl) {
-        Regex pattern = regexp.getPattern();
+        Regex pattern = regexp.getPattern(context);
         Regex prepared = regexp.preparePattern(context, this);
 
         int begin = value.getBegin();
@@ -3352,7 +3352,7 @@ private IRubyObject gsubCommon(ThreadContext context, Block block, RubyString re
 
     private IRubyObject gsubCommon(ThreadContext context, Block block, RubyString repl,
             RubyHash hash, RubyRegexp regexp, final boolean bang, int tuFlags, boolean useBackref) {
-        Regex pattern = regexp.getPattern();
+        Regex pattern = regexp.getPattern(context);
         Regex prepared = regexp.preparePattern(context, this);
 
         final byte[] spBytes = value.getUnsafeBytes();
@@ -3491,8 +3491,9 @@ private IRubyObject indexCommon(ThreadContext context, IRubyObject sub, int pos)
                 return context.nil;
             }
 
-            pos = singleByteOptimizable() ? pos : StringSupport.nth(regexp.checkEncoding(this), value, pos) - value.getBegin();
-            pos = regexp.adjustStartPos(this, pos, false);
+            pos = singleByteOptimizable() ?
+                    pos : StringSupport.nth(regexp.checkEncoding(context, this), value, pos) - value.getBegin();
+            pos = regexp.adjustStartPos(context, this, pos, false);
             pos = regexp.search(context, this, pos, false);
             if (pos >= 0) pos = subLength(context.getLocalMatch().begin(0));
         } else {
@@ -4099,7 +4100,7 @@ private void subpatSet(ThreadContext context, RubyRegexp regexp, IRubyObject bac
         // this cast should be ok, since nil matchdata will be < 0 above
         RubyMatchData match = context.getLocalMatch();
 
-        int nth = backref == null ? 0 : subpatSetCheck(context, match.backrefNumber(context.runtime, backref), match.regs);
+        int nth = backref == null ? 0 : subpatSetCheck(context, match.backrefNumber(context, backref), match.regs);
 
         final int start, end;
         if (match.regs == null) {
@@ -4129,7 +4130,7 @@ private IRubyObject subpat(ThreadContext context, RubyRegexp regex, IRubyObject
             // set backref for user
             context.setBackRef(match);
 
-            return RubyRegexp.nth_match(match.backrefNumber(context.runtime, backref), match);
+            return RubyRegexp.nth_match(context, match.backrefNumber(context, backref), match);
         }
 
         context.clearBackRef();
@@ -4146,7 +4147,7 @@ private IRubyObject subpat(ThreadContext context, RubyRegexp regex) {
             // set backref for user
             context.setBackRef(match);
 
-            return RubyRegexp.nth_match(0, match);
+            return RubyRegexp.nth_match(context, 0, match);
         }
 
         // set backref for user
@@ -4703,7 +4704,7 @@ private Object determineSplitPattern(ThreadContext context, IRubyObject pat) {
         }
 
         if (pattern instanceof RubyRegexp regexp) {
-            if (regexp.isSimpleString()) return regexp.rawSource(); // Simple string-only regexp use Optimized String split
+            if (regexp.isSimpleString(context)) return regexp.rawSource(); // Simple string-only regexp use Optimized String split
             return regexp;
         }
 
@@ -4729,7 +4730,7 @@ private RubyArray regexSplit(ThreadContext context, RubyRegexp pattern, boolean
         byte[] bytes = value.getUnsafeBytes();
         Encoding enc = value.getEncoding();
 
-        boolean captures = pattern.getPattern().numberOfCaptures() != 0;
+        boolean captures = pattern.getPattern(context).numberOfCaptures() != 0;
 
         int end, beg = 0;
         boolean lastNull = false;
@@ -5084,12 +5085,12 @@ private static IRubyObject scanOnce(ThreadContext context, RubyString str, IRuby
                 startp[0] = matchEnd;
             }
             if (match.numRegs() == 1) {
-                return RubyRegexp.nth_match(0, match);
+                return RubyRegexp.nth_match(context, 0, match);
             }
             int size = match.numRegs();
             RubyArray result = RubyArray.newBlankArrayInternal(context.runtime, size - 1);
             for (int i = 1; i < size; i++) {
-                result.eltInternalSet(i - 1, RubyRegexp.nth_match(i, match));
+                result.eltInternalSet(i - 1, RubyRegexp.nth_match(context, i, match));
             }
             result.realLength = size - 1;
 
@@ -5561,7 +5562,7 @@ public IRubyObject rpartition(ThreadContext context, IRubyObject arg) {
             IRubyObject tmp = rindex(context, arg);
             if (tmp.isNil()) return rpartitionMismatch(context);
             pos = tmp.convertToInteger().getIntValue();
-            sep = (RubyString)RubyRegexp.nth_match(0, context.getLocalMatchOrNil());
+            sep = (RubyString)RubyRegexp.nth_match(context, 0, context.getLocalMatchOrNil());
         } else {
             IRubyObject tmp = arg.checkStringType();
             if (tmp.isNil()) throw typeError(context, "type mismatch: ", arg, " given");
diff --git a/core/src/main/java/org/jruby/ext/date/RubyDate.java b/core/src/main/java/org/jruby/ext/date/RubyDate.java
index 5559256905d..ad0e15a098f 100644
--- a/core/src/main/java/org/jruby/ext/date/RubyDate.java
+++ b/core/src/main/java/org/jruby/ext/date/RubyDate.java
@@ -1780,44 +1780,41 @@ static IRubyObject _parse_time(ThreadContext context, IRubyObject self, RubyStri
 
         RubyRegexp re = newRegexpFromCache(context, _parse_time, RE_OPTION_IGNORECASE | RE_OPTION_EXTENDED);
         IRubyObject sub = subSpace(context, str, re);
-        if (sub != context.nil) {
-            RubyMatchData match = (RubyMatchData) sub;
-            final RubyString s1 = (RubyString) match.at(1);
-            final RubyString s2 = matchOrNull(context, match, 2);
-
-            if (s2 != null) hash.fastASet(asSymbol(context, "zone"), s2);
-
-            re = newRegexpFromCache(context, _parse_time2, RE_OPTION_IGNORECASE | RE_OPTION_EXTENDED);
-            sub = re.match_m(context, s1, false);
-            if (sub != context.nil) {
-                match = (RubyMatchData) sub;
-                RubyInteger hour;
-                RubyString m = (RubyString) match.at(1);
-                hash.fastASet(asSymbol(context, "hour"), hour = (RubyInteger) m.to_i(context));
-                m = matchOrNull(context, match, 2);
-                if (m != null) hash.fastASet(asSymbol(context, "min"), m.to_i(context));
-                m = matchOrNull(context, match, 3);
-                if (m != null) hash.fastASet(asSymbol(context, "sec"), m.to_i(context));
-                m = matchOrNull(context, match, 4);
-                if (m != null) {
-                    RubyInteger den = (RubyInteger) asFixnum(context, 10).op_pow(context, m.length());
-                    hash.fastASet(asSymbol(context, "sec_fraction"), RubyRational.newInstance(context, (RubyInteger) m.to_i(context), den));
-                }
-                m = matchOrNull(context, match, 5);
-                if (m != null) {
-                    hour = (RubyInteger) hour.op_mod(context, 12);
-                    if (m.length() == 1 && strPtr(m, 'p') || strPtr(m, 'P')) {
-                        hour = (RubyInteger) hour.op_plus(context, 12);
-                    }
-                    hash.fastASet(asSymbol(context, "hour"), hour);
+        if (!(sub instanceof RubyMatchData match)) return context.nil;
+
+        final RubyString s1 = (RubyString) match.at(context, 1);
+        final RubyString s2 = matchOrNull(context, match, 2);
+
+        if (s2 != null) hash.fastASet(asSymbol(context, "zone"), s2);
+
+        re = newRegexpFromCache(context, _parse_time2, RE_OPTION_IGNORECASE | RE_OPTION_EXTENDED);
+        sub = re.match_m(context, s1, false);
+        if (sub instanceof RubyMatchData match2) {
+            RubyInteger hour;
+            RubyString m = (RubyString) match2.at(context, 1);
+            hash.fastASet(asSymbol(context, "hour"), hour = (RubyInteger) m.to_i(context));
+            m = matchOrNull(context, match2, 2);
+            if (m != null) hash.fastASet(asSymbol(context, "min"), m.to_i(context));
+            m = matchOrNull(context, match2, 3);
+            if (m != null) hash.fastASet(asSymbol(context, "sec"), m.to_i(context));
+            m = matchOrNull(context, match2, 4);
+            if (m != null) {
+                RubyInteger den = (RubyInteger) asFixnum(context, 10).op_pow(context, m.length());
+                hash.fastASet(asSymbol(context, "sec_fraction"), RubyRational.newInstance(context, (RubyInteger) m.to_i(context), den));
+            }
+            m = matchOrNull(context, match2, 5);
+            if (m != null) {
+                hour = (RubyInteger) hour.op_mod(context, 12);
+                if (m.length() == 1 && strPtr(m, 'p') || strPtr(m, 'P')) {
+                    hour = (RubyInteger) hour.op_plus(context, 12);
                 }
-            } else {
-                hash.fastASet(asSymbol(context, "hour"), asFixnum(context, 0));
+                hash.fastASet(asSymbol(context, "hour"), hour);
             }
-
-            return context.tru;
+        } else {
+            hash.fastASet(asSymbol(context, "hour"), asFixnum(context, 0));
         }
-        return sub; // nil
+
+        return context.tru;
     }
 
     private static final ByteList[] ABBR_MONTHS = new ByteList[] {
@@ -1853,12 +1850,11 @@ private static int mon_num(RubyString s) {
     static IRubyObject _parse_day(ThreadContext context, IRubyObject self, RubyString str, RubyHash hash) {
         RubyRegexp re = newRegexpFromCache(context, _parse_day, RE_OPTION_IGNORECASE);
         IRubyObject sub = subSpace(context, str, re);
-        if (sub != context.nil) {
-            int day = day_num((RubyString) ((RubyMatchData) sub).at(1));
-            hash.fastASet(asSymbol(context, "wday"), asFixnum(context, day));
-            return context.tru;
-        }
-        return sub; // nil
+        if (!(sub instanceof RubyMatchData match)) return context.nil;
+
+        int day = day_num((RubyString) match.at(context, 1));
+        hash.fastASet(asSymbol(context, "wday"), asFixnum(context, day));
+        return context.tru;
     }
 
     private static final ByteList _parse_mon;
@@ -1869,13 +1865,12 @@ static IRubyObject _parse_day(ThreadContext context, IRubyObject self, RubyStrin
 
     static IRubyObject _parse_mon(ThreadContext context, IRubyObject self, RubyString str, RubyHash hash) {
         RubyRegexp re = newRegexpFromCache(context, _parse_mon, RE_OPTION_IGNORECASE);
-        IRubyObject sub = subSpace(context, (RubyString) str, re);
-        if (sub != context.nil) {
-            int mon = mon_num((RubyString) ((RubyMatchData) sub).at(1));
-            hash.fastASet(asSymbol(context, "mon"), asFixnum(context, mon));
-            return context.tru;
-        }
-        return sub; // nil
+        IRubyObject sub = subSpace(context, str, re);
+        if (!(sub instanceof RubyMatchData match)) return context.nil;
+
+        int mon = mon_num((RubyString) match.at(context, 1));
+        hash.fastASet(asSymbol(context, "mon"), asFixnum(context, mon));
+        return context.tru;
     }
 
     private static final ByteList _parse_year;
@@ -1887,9 +1882,9 @@ static IRubyObject _parse_mon(ThreadContext context, IRubyObject self, RubyStrin
     static IRubyObject _parse_year(ThreadContext context, IRubyObject self, RubyString str, RubyHash hash) {
         RubyRegexp re = RubyRegexp.newRegexp(context.runtime, _parse_year);
         IRubyObject sub = subSpace(context, str, re);
-        if (sub == context.nil) return context.nil;
+        if (!(sub instanceof RubyMatchData match)) return context.nil;
 
-        hash.fastASet(asSymbol(context, "year"), ((RubyString) ((RubyMatchData) sub).at(1)).to_i(context));
+        hash.fastASet(asSymbol(context, "year"), ((RubyString) match.at(context, 1)).to_i(context));
         return context.tru;
     }
 
@@ -1902,9 +1897,9 @@ static IRubyObject _parse_year(ThreadContext context, IRubyObject self, RubyStri
     static IRubyObject _parse_mday(ThreadContext context, IRubyObject self, RubyString str, RubyHash hash) {
         RubyRegexp re = newRegexpFromCache(context, _parse_mday, RE_OPTION_IGNORECASE);
         IRubyObject sub = subSpace(context, str, re);
-        if (sub == context.nil) return context.nil;
+        if (!(sub instanceof RubyMatchData match)) return context.nil;
 
-        hash.fastASet(asSymbol(context, "mday"), ((RubyString) ((RubyMatchData) sub).at(1)).to_i(context));
+        hash.fastASet(asSymbol(context, "mday"), ((RubyString) match.at(context, 1)).to_i(context));
         return context.tru;
     }
 
@@ -1926,21 +1921,18 @@ static IRubyObject _parse_mday(ThreadContext context, IRubyObject self, RubyStri
 
     static IRubyObject _parse_eu(ThreadContext context, IRubyObject self, RubyString str, RubyHash hash) {
         RubyRegexp re = newRegexpFromCache(context, _parse_eu, RE_OPTION_IGNORECASE);
-        IRubyObject sub = subSpace(context, (RubyString) str, re);
-        if (sub != context.nil) {
-            final RubyMatchData match = (RubyMatchData) sub;
+        IRubyObject sub = subSpace(context, str, re);
+        if (!(sub instanceof RubyMatchData match)) return context.nil;
 
-            RubyString d = (RubyString) match.at(1);
-            RubyString mon = (RubyString) match.at(2);
-            mon = RubyString.newStringShared(context.runtime, ConvertBytes.byteToSharedByteList((short) mon_num(mon)));
-            RubyString b = matchOrNull(context, match, 3);
-            RubyString y = matchOrNull(context, match, 4);
+        RubyString d = (RubyString) match.at(context, 1);
+        RubyString mon = (RubyString) match.at(context, 2);
+        mon = RubyString.newStringShared(context.runtime, ConvertBytes.byteToSharedByteList((short) mon_num(mon)));
+        RubyString b = matchOrNull(context, match, 3);
+        RubyString y = matchOrNull(context, match, 4);
 
-            s3e(context, hash, y, mon, d, b != null && b.length() > 1 && (b.charAt(0) == 'B' || b.charAt(0) == 'b'));
+        s3e(context, hash, y, mon, d, b != null && b.length() > 1 && (b.charAt(0) == 'B' || b.charAt(0) == 'b'));
 
-            return context.tru;
-        }
-        return sub; // nil
+        return context.tru;
     }
 
     private static final ByteList _parse_us;
@@ -1963,13 +1955,11 @@ static IRubyObject _parse_eu(ThreadContext context, IRubyObject self, RubyString
     static IRubyObject _parse_us(ThreadContext context, IRubyObject self, RubyString str, RubyHash hash) {
         RubyRegexp re = newRegexpFromCache(context, _parse_us, RE_OPTION_IGNORECASE);
         IRubyObject sub = subSpace(context, str, re);
-        if (sub == context.nil) return context.nil;
+        if (!(sub instanceof RubyMatchData match)) return context.nil;
 
-        final RubyMatchData match = (RubyMatchData) sub;
-
-        RubyString mon = (RubyString) match.at(1);
+        RubyString mon = (RubyString) match.at(context, 1);
         mon = RubyString.newStringShared(context.runtime, ConvertBytes.byteToSharedByteList((short) mon_num(mon)));
-        RubyString d = (RubyString) match.at(2);
+        RubyString d = (RubyString) match.at(context, 2);
         RubyString b = matchOrNull(context, match, 3);
         RubyString y = matchOrNull(context, match, 4);
 
@@ -1986,7 +1976,7 @@ private static RubyRegexp newRegexpFromCache(ThreadContext context, ByteList str
     }
 
     private static RubyString matchOrNull(ThreadContext context, final RubyMatchData match, int i) {
-        IRubyObject val = match.at(i);
+        IRubyObject val = match.at(context, i);
         return val == context.nil ? null : (RubyString) val;
     }
 
@@ -1997,15 +1987,13 @@ private static RubyString matchOrNull(ThreadContext context, final RubyMatchData
     }
 
     static IRubyObject _parse_iso(ThreadContext context, IRubyObject self, RubyString str, RubyHash hash) {
-        final Ruby runtime = context.runtime;
-        RubyRegexp re = RubyRegexp.newRegexp(runtime, _parse_iso);
-        IRubyObject sub = subSpace(context, (RubyString) str, re);
-        if (sub != context.nil) {
-            final RubyMatchData match = (RubyMatchData) sub;
-            s3e(context, hash, (RubyString) match.at(1), (RubyString) match.at(2), (RubyString) match.at(3), false);
-            return context.tru;
-        }
-        return sub; // nil
+        RubyRegexp re = RubyRegexp.newRegexp(context.runtime, _parse_iso);
+        IRubyObject sub = subSpace(context, str, re);
+        if (!(sub instanceof RubyMatchData match)) return context.nil;
+
+        s3e(context, hash, (RubyString) match.at(context, 1), (RubyString) match.at(context, 2),
+                (RubyString) match.at(context, 3), false);
+        return context.tru;
     }
 
     private static final ByteList _parse_sla;
@@ -2080,9 +2068,9 @@ static void parse_frag(ThreadContext context, IRubyObject self, RubyString str,
 
         if (hashGet(context, hash, "hour") != null && hashGet(context, hash, "mday") == null) {
             RubyRegexp re = newRegexpFromCache(context, _parse_frag, RE_OPTION_IGNORECASE);
-            sub = subSpace(context, (RubyString) str, re);
-            if (sub != context.nil) {
-                RubyInteger v = (RubyInteger) ((RubyString) ((RubyMatchData) sub).at(1)).to_i(context);
+            sub = subSpace(context, str, re);
+            if (sub instanceof RubyMatchData match) {
+                RubyInteger v = (RubyInteger) ((RubyString) match.at(context, 1)).to_i(context);
                 long vi = v.getLongValue();
                 if (1 <= vi && vi <= 31) hash.fastASet(asSymbol(context, "mday"), v);
             }
@@ -2093,8 +2081,8 @@ static void parse_frag(ThreadContext context, IRubyObject self, RubyString str,
                 RubyRegexp re = newRegexpFromCache(context, _parse_frag, RE_OPTION_IGNORECASE);
                 sub = subSpace(context, str, re);
             }
-            if (sub != context.nil) {
-                RubyInteger v = (RubyInteger) ((RubyString) ((RubyMatchData) sub).at(1)).to_i(context);
+            if (sub instanceof RubyMatchData match) {
+                RubyInteger v = (RubyInteger) ((RubyString) match.at(context, 1)).to_i(context);
                 long vi = v.getLongValue();
                 if (0 <= vi && vi <= 24) hash.fastASet(asSymbol(context, "hour"), v);
             }
diff --git a/core/src/main/java/org/jruby/ir/instructions/BuildBackrefInstr.java b/core/src/main/java/org/jruby/ir/instructions/BuildBackrefInstr.java
index e3708c0a1e3..fab661d113b 100644
--- a/core/src/main/java/org/jruby/ir/instructions/BuildBackrefInstr.java
+++ b/core/src/main/java/org/jruby/ir/instructions/BuildBackrefInstr.java
@@ -51,9 +51,9 @@ public Object interpret(ThreadContext context, StaticScope currScope, DynamicSco
 
         switch (type) {
         case '&' : return RubyRegexp.last_match(backref);
-        case '`' : return RubyRegexp.match_pre(backref);
+        case '`' : return RubyRegexp.match_pre(context, backref);
         case '\'': return RubyRegexp.match_post(backref);
-        case '+' : return RubyRegexp.match_last(backref);
+        case '+' : return RubyRegexp.match_last(context, backref);
         default:
             assert false: "backref with invalid type";
             return null;
diff --git a/core/src/main/java/org/jruby/ir/runtime/IRRuntimeHelpers.java b/core/src/main/java/org/jruby/ir/runtime/IRRuntimeHelpers.java
index 50da76ede21..dba1b11a07b 100644
--- a/core/src/main/java/org/jruby/ir/runtime/IRRuntimeHelpers.java
+++ b/core/src/main/java/org/jruby/ir/runtime/IRRuntimeHelpers.java
@@ -1000,13 +1000,8 @@ public static IRubyObject isDefinedGlobal(ThreadContext context, String name, IR
     public static IRubyObject isDefinedNthRef(ThreadContext context, int matchNumber, IRubyObject definedMessage) {
         IRubyObject backref = context.getBackRef();
 
-        if (backref instanceof RubyMatchData) {
-            if (!((RubyMatchData) backref).group(matchNumber).isNil()) {
-                return definedMessage;
-            }
-        }
-
-        return context.nil;
+        return backref instanceof RubyMatchData match && !match.group(context, matchNumber).isNil() ?
+                definedMessage : context.nil;
     }
 
     @JIT @Interp
@@ -1070,7 +1065,7 @@ public static IRubyObject isDefinedSuper(ThreadContext context, IRubyObject rece
     }
 
     public static IRubyObject nthMatch(ThreadContext context, int matchNumber) {
-        return RubyRegexp.nth_match(matchNumber, context.getBackRef());
+        return RubyRegexp.nth_match(context, matchNumber, context.getBackRef());
     }
 
     public static void defineAlias(ThreadContext context, IRubyObject self, DynamicScope currDynScope,
@@ -1342,9 +1337,9 @@ public static IRubyObject receiveKeywordRestArg(ThreadContext context, IRubyObje
     public static IRubyObject setCapturedVar(ThreadContext context, IRubyObject matchRes, String id) {
         if (matchRes.isNil()) return context.nil;
 
-        IRubyObject backref = context.getBackRef();
+        RubyMatchData backref = (RubyMatchData) context.getBackRef();
 
-        return RubyRegexp.nth_match(((RubyMatchData) backref).getNameToBackrefNumber(id), backref);
+        return RubyRegexp.nth_match(context, backref.getNameToBackrefNumber(context, id), backref);
     }
 
     @JIT // for JVM6
diff --git a/core/src/main/java/org/jruby/runtime/Helpers.java b/core/src/main/java/org/jruby/runtime/Helpers.java
index bd46d0d6119..2b12a7a018d 100644
--- a/core/src/main/java/org/jruby/runtime/Helpers.java
+++ b/core/src/main/java/org/jruby/runtime/Helpers.java
@@ -1076,30 +1076,22 @@ public static Block getBlockFromBlockPassBody(IRubyObject proc, Block currentBlo
 
     @Deprecated
     public static IRubyObject backrefLastMatch(ThreadContext context) {
-        IRubyObject backref = context.getBackRef();
-
-        return RubyRegexp.last_match(backref);
+        return RubyRegexp.last_match(context.getBackRef());
     }
 
     @Deprecated
     public static IRubyObject backrefMatchPre(ThreadContext context) {
-        IRubyObject backref = context.getBackRef();
-
-        return RubyRegexp.match_pre(backref);
+        return RubyRegexp.match_pre(context, context.getBackRef());
     }
 
     @Deprecated
     public static IRubyObject backrefMatchPost(ThreadContext context) {
-        IRubyObject backref = context.getBackRef();
-
-        return RubyRegexp.match_post(backref);
+        return RubyRegexp.match_post(context.getBackRef());
     }
 
     @Deprecated
     public static IRubyObject backrefMatchLast(ThreadContext context) {
-        IRubyObject backref = context.getBackRef();
-
-        return RubyRegexp.match_last(backref);
+        return RubyRegexp.match_last(context, context.getBackRef());
     }
 
     public static IRubyObject[] appendToObjectArray(IRubyObject[] array, IRubyObject add) {
diff --git a/core/src/main/java/org/jruby/runtime/ThreadContext.java b/core/src/main/java/org/jruby/runtime/ThreadContext.java
index 0fa4edd3386..c7dc841d820 100644
--- a/core/src/main/java/org/jruby/runtime/ThreadContext.java
+++ b/core/src/main/java/org/jruby/runtime/ThreadContext.java
@@ -640,21 +640,23 @@ public IRubyObject getBackRef() {
     /**
      * MRI: rb_reg_last_match
      */
+    @JIT
     public IRubyObject last_match() {
-        return RubyRegexp.nth_match(0, frameStack[frameIndex].getBackRef(nil));
+        return RubyRegexp.nth_match(this, 0, frameStack[frameIndex].getBackRef(nil));
     }
 
     /**
      * MRI: rb_reg_match_pre
      */
+    @JIT
     public IRubyObject match_pre() {
-        return RubyRegexp.match_pre(frameStack[frameIndex].getBackRef(nil));
+        return RubyRegexp.match_pre(this, frameStack[frameIndex].getBackRef(nil));
     }
 
-
     /**
      * MRI: rb_reg_match_post
      */
+    @JIT
     public IRubyObject match_post() {
         return RubyRegexp.match_post(frameStack[frameIndex].getBackRef(nil));
     }
@@ -662,8 +664,9 @@ public IRubyObject match_post() {
     /**
      * MRI: rb_reg_match_last
      */
+    @JIT
     public IRubyObject match_last() {
-        return RubyRegexp.match_last(frameStack[frameIndex].getBackRef(nil));
+        return RubyRegexp.match_last(this, frameStack[frameIndex].getBackRef(nil));
     }
 
     /**
diff --git a/core/src/main/java/org/jruby/util/RegexpOptions.java b/core/src/main/java/org/jruby/util/RegexpOptions.java
index ff75c97abca..cb682ee36ad 100644
--- a/core/src/main/java/org/jruby/util/RegexpOptions.java
+++ b/core/src/main/java/org/jruby/util/RegexpOptions.java
@@ -11,6 +11,7 @@
 import org.jcodings.specific.UTF8Encoding;
 import org.jruby.Ruby;
 import org.jruby.RubyRegexp;
+import org.jruby.runtime.ThreadContext;
 
 import static org.jruby.api.Create.newString;
 import static org.jruby.api.Error.argumentError;
@@ -236,8 +237,12 @@ public static RegexpOptions fromJoniOptions(int joniOptions) {
         return options;
     }
 
-    // This is the options Regexp#new supports.  It is not all valid suffixes.
     public static RegexpOptions fromByteList(Ruby runtime, ByteList string) {
+        return fromByteList(runtime.getCurrentContext(), string);
+    }
+
+    // This is the options Regexp#new supports.  It is not all valid suffixes.
+    public static RegexpOptions fromByteList(ThreadContext context, ByteList string) {
         RegexpOptions options = new RegexpOptions();
         byte[] bytes = string.unsafeBytes();
         int length = string.realSize();
@@ -258,8 +263,7 @@ public static RegexpOptions fromByteList(Ruby runtime, ByteList string) {
                     options.setOnce(true);
                     break;
                 default:
-                    throw argumentError(runtime.getCurrentContext(),
-                            str(runtime, "unknown regexp option: ", newString(runtime.getCurrentContext(), string)));
+                    throw argumentError(context, str(context.runtime, "unknown regexp option: ", newString(context, string)));
             }
         }
 
diff --git a/core/src/test/java/org/jruby/TestRegexpCache.java b/core/src/test/java/org/jruby/TestRegexpCache.java
index f4eb986594c..5d5ee886424 100644
--- a/core/src/test/java/org/jruby/TestRegexpCache.java
+++ b/core/src/test/java/org/jruby/TestRegexpCache.java
@@ -22,11 +22,11 @@ public void testCacheRetention() {
         //assertSame(regex, RubyRegexp.getQuotedRegexpFromCache(runtime, GH2078_TEST_BYTELIST.dup(), RegexpOptions.NULL_OPTIONS, false));
         RubyString str = newString(context, ByteList.create("GH2078"));
 
-        Regex regex = RubyRegexp.getQuotedRegexpFromCache(context.runtime, str, RegexpOptions.NULL_OPTIONS);
-        assertSame(regex, RubyRegexp.getQuotedRegexpFromCache(context.runtime, str, RegexpOptions.NULL_OPTIONS));
-        assertSame(regex, RubyRegexp.getQuotedRegexpFromCache(context.runtime, (RubyString) str.dup(), RegexpOptions.NULL_OPTIONS));
-        assertSame(regex, RubyRegexp.getQuotedRegexpFromCache(context.runtime, newString(context, "GH2078"), RegexpOptions.NULL_OPTIONS));
-        assertSame(regex, RubyRegexp.getQuotedRegexpFromCache(context.runtime, str.newFrozen(), RegexpOptions.NULL_OPTIONS));
+        Regex regex = RubyRegexp.getQuotedRegexpFromCache(context, str, RegexpOptions.NULL_OPTIONS);
+        assertSame(regex, RubyRegexp.getQuotedRegexpFromCache(context, str, RegexpOptions.NULL_OPTIONS));
+        assertSame(regex, RubyRegexp.getQuotedRegexpFromCache(context, (RubyString) str.dup(), RegexpOptions.NULL_OPTIONS));
+        assertSame(regex, RubyRegexp.getQuotedRegexpFromCache(context, newString(context, "GH2078"), RegexpOptions.NULL_OPTIONS));
+        assertSame(regex, RubyRegexp.getQuotedRegexpFromCache(context, str.newFrozen(), RegexpOptions.NULL_OPTIONS));
 
         // Should only have one entry
         assertEquals(1, RubyRegexp.quotedPatternCache.size());