diff --git a/Libraries/LibRegex/RegexByteCode.h b/Libraries/LibRegex/RegexByteCode.h
index 75a4a8c7949..75105de29a7 100644
--- a/Libraries/LibRegex/RegexByteCode.h
+++ b/Libraries/LibRegex/RegexByteCode.h
@@ -791,7 +791,13 @@ public:
     ByteString arguments_string() const override
     {
         auto reps = id() < state().repetition_marks.size() ? state().repetition_marks.at(id()) : 0;
-        return ByteString::formatted("offset={} count={} id={} rep={}, sp: {}", offset(), count() + 1, id(), reps + 1, state().string_position);
+        return ByteString::formatted("offset={} [&{}] count={} id={} rep={}, sp: {}",
+            static_cast<ssize_t>(offset()),
+            state().instruction_position - offset(),
+            count() + 1,
+            id(),
+            reps + 1,
+            state().string_position);
     }
 };
 
diff --git a/Libraries/LibRegex/RegexMatcher.h b/Libraries/LibRegex/RegexMatcher.h
index 884bc93d521..666a4d67109 100644
--- a/Libraries/LibRegex/RegexMatcher.h
+++ b/Libraries/LibRegex/RegexMatcher.h
@@ -28,6 +28,7 @@ namespace Detail {
 struct Block {
     size_t start;
     size_t end;
+    StringView comment { "N/A"sv };
 };
 
 }
diff --git a/Libraries/LibRegex/RegexOptimizer.cpp b/Libraries/LibRegex/RegexOptimizer.cpp
index df8b1ac0b2c..b3d08d935c2 100644
--- a/Libraries/LibRegex/RegexOptimizer.cpp
+++ b/Libraries/LibRegex/RegexOptimizer.cpp
@@ -59,18 +59,18 @@ typename Regex<Parser>::BasicBlockList Regex<Parser>::split_basic_blocks(ByteCod
         auto& op = static_cast<T const&>(opcode);
         ssize_t jump_offset = op.size() + op.offset();
         if (jump_offset >= 0) {
-            block_boundaries.append({ end_of_last_block, state.instruction_position });
+            block_boundaries.append({ end_of_last_block, state.instruction_position, "Jump ahead"sv });
             end_of_last_block = state.instruction_position + opcode.size();
         } else {
             // This op jumps back, see if that's within this "block".
             if (jump_offset + state.instruction_position > end_of_last_block) {
                 // Split the block!
-                block_boundaries.append({ end_of_last_block, jump_offset + state.instruction_position });
-                block_boundaries.append({ jump_offset + state.instruction_position, state.instruction_position });
+                block_boundaries.append({ end_of_last_block, jump_offset + state.instruction_position, "Jump back 1"sv });
+                block_boundaries.append({ jump_offset + state.instruction_position, state.instruction_position, "Jump back 2"sv });
                 end_of_last_block = state.instruction_position + opcode.size();
             } else {
                 // Nope, it's just a jump to another block
-                block_boundaries.append({ end_of_last_block, state.instruction_position });
+                block_boundaries.append({ end_of_last_block, state.instruction_position, "Jump"sv });
                 end_of_last_block = state.instruction_position + opcode.size();
             }
         }
@@ -92,15 +92,16 @@ typename Regex<Parser>::BasicBlockList Regex<Parser>::split_basic_blocks(ByteCod
             check_jump.template operator()<OpCode_ForkStay>(opcode);
             break;
         case OpCodeId::FailForks:
-            block_boundaries.append({ end_of_last_block, state.instruction_position });
+            block_boundaries.append({ end_of_last_block, state.instruction_position, "FailForks"sv });
             end_of_last_block = state.instruction_position + opcode.size();
             break;
         case OpCodeId::Repeat: {
             // Repeat produces two blocks, one containing its repeated expr, and one after that.
-            auto repeat_start = state.instruction_position - static_cast<OpCode_Repeat const&>(opcode).offset();
+            auto& repeat = static_cast<OpCode_Repeat const&>(opcode);
+            auto repeat_start = state.instruction_position - repeat.offset() - repeat.size();
             if (repeat_start > end_of_last_block)
-                block_boundaries.append({ end_of_last_block, repeat_start });
-            block_boundaries.append({ repeat_start, state.instruction_position });
+                block_boundaries.append({ end_of_last_block, repeat_start, "Repeat"sv });
+            block_boundaries.append({ repeat_start, state.instruction_position, "Repeat after"sv });
             end_of_last_block = state.instruction_position + opcode.size();
             break;
         }
@@ -116,7 +117,7 @@ typename Regex<Parser>::BasicBlockList Regex<Parser>::split_basic_blocks(ByteCod
     }
 
     if (end_of_last_block < bytecode_size)
-        block_boundaries.append({ end_of_last_block, bytecode_size });
+        block_boundaries.append({ end_of_last_block, bytecode_size, "End"sv });
 
     quick_sort(block_boundaries, [](auto& a, auto& b) { return a.start < b.start; });
 
@@ -664,7 +665,7 @@ void Regex<Parser>::attempt_rewrite_loops_as_atomic_groups(BasicBlockList const&
         RegexDebug dbg;
         dbg.print_bytecode(*this);
         for (auto const& block : basic_blocks)
-            dbgln("block from {} to {}", block.start, block.end);
+            dbgln("block from {} to {} (comment: {})", block.start, block.end, block.comment);
     }
 
     // A pattern such as:
@@ -1221,6 +1222,7 @@ void Optimizer::append_alternation(ByteCode& target, Span<ByteCode> alternatives
                 ssize_t jump_offset;
                 auto is_jump = true;
                 auto patch_location = state.instruction_position + 1;
+                bool should_negate = false;
 
                 switch (opcode.opcode_id()) {
                 case OpCodeId::Jump:
@@ -1243,6 +1245,7 @@ void Optimizer::append_alternation(ByteCode& target, Span<ByteCode> alternatives
                     break;
                 case OpCodeId::Repeat:
                     jump_offset = static_cast<ssize_t>(0) - static_cast<ssize_t>(static_cast<OpCode_Repeat const&>(opcode).offset()) - static_cast<ssize_t>(opcode.size());
+                    should_negate = true;
                     break;
                 default:
                     is_jump = false;
@@ -1272,7 +1275,10 @@ void Optimizer::append_alternation(ByteCode& target, Span<ByteCode> alternatives
                                 intended_jump_ip);
                             VERIFY_NOT_REACHED();
                         }
-                        target[patch_location] = static_cast<ByteCodeValueType>(*target_ip - patch_location - 1);
+                        ssize_t target_value = *target_ip - patch_location - 1;
+                        if (should_negate)
+                            target_value = -target_value + 2; // from -1 to +1.
+                        target[patch_location] = static_cast<ByteCodeValueType>(target_value);
                     } else {
                         patch_locations.append({ QualifiedIP { ip.alternative_index, intended_jump_ip }, patch_location });
                     }