diff --git a/lib/compiler/src/beam_ssa_codegen.erl b/lib/compiler/src/beam_ssa_codegen.erl
index 711e77684684..2ed93d5e182c 100644
--- a/lib/compiler/src/beam_ssa_codegen.erl
+++ b/lib/compiler/src/beam_ssa_codegen.erl
@@ -2267,6 +2267,10 @@ bs_translate([]) -> [].
 
 bs_translate_collect([I|Is]=Is0, Ctx, Fail, Acc) ->
     case bs_translate_instr(I) of
+        {Ctx,_,{ensure_at_least,_,_}} ->
+            %% There should only be a single `ensure_at_least`
+            %% instruction in each `bs_match` instruction.
+            {bs_translate_fixup(Acc),Fail,Is0};
         {Ctx,Fail,Instr} ->
             bs_translate_collect(Is, Ctx, Fail, [Instr|Acc]);
         {Ctx,{f,0},Instr} ->
diff --git a/lib/compiler/src/beam_ssa_opt.erl b/lib/compiler/src/beam_ssa_opt.erl
index 9a80933aca99..fce063643671 100644
--- a/lib/compiler/src/beam_ssa_opt.erl
+++ b/lib/compiler/src/beam_ssa_opt.erl
@@ -307,8 +307,8 @@ late_epilogue_passes(Opts) ->
           ?PASS(ssa_opt_sink),
           ?PASS(ssa_opt_blockify),
           ?PASS(ssa_opt_redundant_br),
-          ?PASS(ssa_opt_bs_ensure),
           ?PASS(ssa_opt_merge_blocks),
+          ?PASS(ssa_opt_bs_ensure),
           ?PASS(ssa_opt_try),
           ?PASS(ssa_opt_get_tuple_element),
           ?PASS(ssa_opt_tail_literals),
@@ -3536,7 +3536,7 @@ redundant_br_safe_bool(Is, Bool) ->
     end.
 
 %%%
-%%% Add the bs_ensure instruction before a sequence of `bs_match`
+%%% Add the `bs_ensure` instruction before a sequence of `bs_match`
 %%% (SSA) instructions, each having a literal size and the
 %%% same failure label.
 %%%
@@ -3544,6 +3544,15 @@ redundant_br_safe_bool(Is, Bool) ->
 %%% instruction that can match multiple segments having the same
 %%% failure label.
 %%%
+%%% It is beneficial but not essential to run this pass after
+%%% the `merge_blocks/1` pass. For the following example, two separate
+%%% `bs_match/1` instructions will emitted if blocks have not been
+%%% merged before this pass:
+%%%
+%%%    A = 0,
+%%%    B = <<1, 2, 3>>,
+%%%    <<A, B:(byte_size(B))/binary>> = <<0, 1, 2, 3>>
+%%%
 
 ssa_opt_bs_ensure({#opt_st{ssa=Blocks0,cnt=Count0,anno=Anno0}=St, FuncDb})
   when is_map(Blocks0) ->
diff --git a/lib/compiler/test/bs_match_SUITE.erl b/lib/compiler/test/bs_match_SUITE.erl
index 9211af62aade..2b06ec0a8de0 100644
--- a/lib/compiler/test/bs_match_SUITE.erl
+++ b/lib/compiler/test/bs_match_SUITE.erl
@@ -2749,6 +2749,8 @@ bs_match(_Config) ->
 
     {'EXIT',{{badmatch,<<>>},_}} = catch do_bs_match_gh_7467(<<>>),
 
+    {0,<<1,2,3>>} = do_bs_match_gh_8280(),
+
     ok.
 
 do_bs_match_1(_, X) ->
@@ -2823,6 +2825,12 @@ do_bs_match_gh_6755(B) ->
 do_bs_match_gh_7467(A) ->
     do_bs_match_gh_7467(<<_:1/bits>> = A).
 
+do_bs_match_gh_8280() ->
+    A = 0,
+    B = <<1, 2, 3>>,
+    <<A, B:(byte_size(B))/binary>> = id(<<0, 1, 2, 3>>),
+    {A, B}.
+
 %% GH-6348/OTP-18297: Allow aliases for binaries.
 -record(ba_foo, {a,b,c}).
 
diff --git a/lib/debugger/src/dbg_ieval.erl b/lib/debugger/src/dbg_ieval.erl
index adb4b153159f..3925b881b0b1 100644
--- a/lib/debugger/src/dbg_ieval.erl
+++ b/lib/debugger/src/dbg_ieval.erl
@@ -1549,6 +1549,9 @@ guard_expr({'orelse',_,E1,E2}, Bs) ->
 		{value,_Val}=Res -> Res
 	    end
     end;
+guard_expr({'case',_,E0,Cs}, Bs) ->
+    {value,E} = guard_expr(E0, Bs),
+    guard_case_clauses(E, Cs, Bs);
 guard_expr({dbg,_,self,[]}, _) ->
     {value,get(self)};
 guard_expr({safe_bif,_,erlang,'not',As0}, Bs) ->
@@ -1591,6 +1594,20 @@ guard_expr({bin,_,Flds}, Bs) ->
 			   end),
     {value,V}.
 
+%% guard_case_clauses(Value, Clauses, Bindings, Error, Ieval)
+%%   Error = try_clause | case_clause
+guard_case_clauses(Val, [{clause,_,[P],G,B}|Cs], Bs0) ->
+    case match(P, Val, Bs0) of
+	{match,Bs} ->
+	    case guard(G, Bs) of
+		true ->
+		    guard_expr(hd(B), Bs);
+		false ->
+		    guard_case_clauses(Val, Cs, Bs0)
+	    end;
+	nomatch ->
+	    guard_case_clauses(Val, Cs, Bs0)
+    end.
 
 %% eval_map_fields([Field], Bindings, IEvalState) ->
 %%  {[{map_assoc | map_exact,Key,Value}],Bindings}
diff --git a/lib/debugger/test/record_SUITE.erl b/lib/debugger/test/record_SUITE.erl
index 2f75dcda4245..e3d66804bbc8 100644
--- a/lib/debugger/test/record_SUITE.erl
+++ b/lib/debugger/test/record_SUITE.erl
@@ -28,7 +28,8 @@
 -export([all/0, suite/0,groups/0,init_per_group/2,end_per_group/2,
 	 init_per_testcase/2,end_per_testcase/2,
 	 init_per_suite/1,end_per_suite/1,
-	 errors/1,record_test/1,eval_once/1]).
+         errors/1,record_test/1,eval_once/1,
+         nested_in_guard/1]).
 
 -export([debug/0]).
 
@@ -50,7 +51,7 @@ end_per_group(_GroupName, Config) ->
 
 
 cases() -> 
-    [errors, record_test, eval_once].
+    [errors, record_test, eval_once, nested_in_guard].
 
 init_per_testcase(_Case, Config) ->
     test_lib:interpret(?MODULE),
@@ -295,6 +296,30 @@ once(Test, Record) ->
     end,
     Result.
 
+nested_in_guard(_Config) ->
+    B = #bar{d = []},
+    F = #foo{a = B},
+
+    ok = do_nested_in_guard(#foo{a=#bar{d=[]}}),
+    not_ok = do_nested_in_guard(#foo{a=#bar{}}),
+    not_ok = do_nested_in_guard(#foo{a={no_bar,a,b,c,d}}),
+    not_ok = do_nested_in_guard(#foo{a={bar,a}}),
+    not_ok = do_nested_in_guard(42),
+    not_ok = do_nested_in_guard(#bar{}),
+    not_ok = do_nested_in_guard([]),
+
+    ok.
+
+-define(is_foo(X), (((X#foo.a)#bar.d == []))).
+
+do_nested_in_guard(F) ->
+    if
+        ?is_foo(F) ->
+            ok;
+        true ->
+            not_ok
+    end.
+
 id(I) ->
     I.