diff --git a/src/test/java/picocli/Issue2342.java b/src/test/java/picocli/Issue2342.java
index 667d9859b..925ed9160 100644
--- a/src/test/java/picocli/Issue2342.java
+++ b/src/test/java/picocli/Issue2342.java
@@ -1,19 +1,157 @@
 package picocli;
 
+import org.junit.Ignore;
 import org.junit.Test;
+import picocli.CommandLine.Model.ArgSpec;
+import picocli.CommandLine.Model.CommandSpec;
 import picocli.CommandLine.Option;
 
 import java.util.ArrayList;
 import java.util.Arrays;
 import java.util.List;
+import java.util.Map;
+import java.util.Stack;
 
 import static org.junit.Assert.*;
 
 public class Issue2342 {
     static class CompileOptions {
-        @Option(names = { "--compiler-arguments" }, split = " ", arity = "*",
+        @Option(names = { "--compiler-arguments" }, split = " ",
+            preprocessor = MyParamProcessor.class,
             description = "Compiler arguments to use to compile generated sources.")
         private List<String> compilerArguments;
+
+        @Option(names = "--target", description = "Test for presence in compiler arguments")
+        private String target;
+
+    }
+
+    static class MyParamProcessor implements CommandLine.IParameterPreprocessor {
+
+        public boolean preprocess(Stack<String> args, CommandSpec commandSpec, ArgSpec argSpec, Map<String, Object> info) {
+            List<String> copy = new ArrayList<String>();
+            while (!args.isEmpty()) {
+                copy.add(args.pop());
+            }
+            if (copy.isEmpty()) {
+                return false; // let picocli generate an exception, --compiler-arguments needs some parameters
+            }
+            if (copy.contains("--target")) {
+                // push last "--target" option and its parameter value back onto the stack
+                String value = null;
+                do {
+                    value = copy.remove(copy.size() - 1);
+                    args.push(value);
+                } while (!"--target".equals(value));
+            }
+            // trim quotes if requested
+            if (commandSpec.parser().trimQuotes()) {
+                for (int i = 0; i < copy.size(); i++) {
+                    String value = copy.get(i);
+                    if (value.startsWith("\"") && value.endsWith("\"")
+                    || value.startsWith("'") && value.endsWith("'")) {
+                        value = value.substring(1, value.length() - 1);
+                        copy.set(i, value);
+                    }
+                }
+            }
+
+            argSpec.setValue(copy);
+            return true; // tell picocli that processing for --compiler-arguments is done
+        }
+    }
+
+    @Ignore("I don't understand how this could be specified on the command line: " +
+        "quoted values, but still somehow the shell would pass 3 separate String values " +
+        "( \"--parameters,  --target and 21\" ) to the Java application?")
+    @Test
+    public void testArgsWithCompilerArgumentsSingleQuoteOnValue() {
+        CompileOptions co = new CompileOptions();
+        String[] args = new String[] {
+            "--compiler-arguments",
+            "'--parameters",
+            "--target",
+            "21'",
+            "--target",
+            "my-file.jar"
+        };
+        new CommandLine(co).parseArgs(args);
+
+        // expect compilerArguments: "--parameters", "--target", "21"
+        // expect target: "my-file.jar"
+        String[] expected = new String[] {
+            "--parameters", "--target", "21",
+        };
+        assertArrayEquals(expected, co.compilerArguments.toArray());
+        assertEquals("my-file.jar", co.target);
+    }
+
+    @Ignore("I don't understand how this could be specified on the command line: " +
+        "quoted values, but still somehow the shell would pass 3 separate String values " +
+        "( \"--parameters,  --target and 21\" ) to the Java application?")
+    @Test
+    public void testArgsWithCompilerArgumentsDoubleQuoteOnValue() {
+        CompileOptions co = new CompileOptions();
+        String[] args = new String[] {
+            "--compiler-arguments",
+            "\"--parameters",
+            "--target",
+            "21\"",
+            "--target",
+            "my-file.jar"
+        };
+        new CommandLine(co).parseArgs(args);
+        // expect compilerArguments: "--parameters", "--target", "21"
+        // expect target: "my-file.jar"
+        String[] expected = new String[] {
+            "--parameters", "--target", "21",
+        };
+        assertArrayEquals(expected, co.compilerArguments.toArray());
+        assertEquals("my-file.jar", co.target);
+    }
+
+    @Ignore("You really need --compiler-arguments to be included in the quoted value, and still be recognized as an option?")
+    @Test
+    public void testArgsWithCompilerArgumentsSingleQuote() {
+        CompileOptions co = new CompileOptions();
+        String[] args = new String[] {
+            "'--compiler-arguments",
+            "--parameters",
+            "--target",
+            "21'",
+            "--target",
+            "my-file.jar"
+        };
+        new CommandLine(co).parseArgs(args);
+        // expect compilerArguments: "--parameters", "--target", "21"
+        // expect target: "my-file.jar"
+        String[] expected = new String[] {
+            "--parameters", "--target", "21",
+        };
+        assertArrayEquals(expected, co.compilerArguments.toArray());
+        assertEquals("my-file.jar", co.target);
+    }
+
+    @Ignore("You really need --compiler-arguments to be included in the quoted value, and still be recognized as an option?")
+    @Test
+    public void testArgsWithCompilerArgumentsDoubleQuote() {
+        CompileOptions co = new CompileOptions();
+        String[] args = new String[] {
+            "\"--compiler-arguments",
+            "--parameters",
+            "--target",
+            "21\"",
+            "--target",
+            "my-file.jar"
+        };
+        new CommandLine(co).parseArgs(args);
+        // expect compilerArguments: "--parameters", "--target", "21"
+        // expect target: "my-file.jar"
+        String[] expected = new String[] {
+            "--parameters", "--target", "21",
+        };
+        assertArrayEquals(expected, co.compilerArguments.toArray());
+        assertEquals("my-file.jar", co.target);
     }
 
     @Test
@@ -48,7 +186,7 @@ public void testSingleQuotesAreNotSupported() {
         new CommandLine(co).parseArgs(args);
 
         String[] expected = new String[] {
-            "'--a-param", "with", "space'", "--parameters", "'--release", "21'", "--nowarn"
+            "'--a-param with space'", "--parameters", "'--release 21'", "--nowarn"
         };
         assertArrayEquals(expected, co.compilerArguments.toArray());
     }
@@ -70,7 +208,7 @@ public void testArgsWithSpacesQuotesTrimmed() {
         // note: .setTrimQuotes(true)
         // results in "--a-param with space" being treated as 3 separate values
         List<String> expected = Arrays.asList(
-            "--a-param", "with", "space", "--parameters", "--release", "21", "--nowarn");
+            "--a-param with space", "--parameters", "--release 21", "--nowarn");
         assertEquals(expected, co.compilerArguments);
     }