diff --git a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexInterpreter.cs b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexInterpreter.cs
index 8d49e71e3b90aa..6abfc4a1509d5d 100644
--- a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexInterpreter.cs
+++ b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexInterpreter.cs
@@ -521,12 +521,10 @@ private bool TryMatchAtCurrentPosition(ReadOnlySpan<char> inputSpan)
                             }
                             else
                             {
-                                // The inner expression found an empty match, so we'll go directly to 'back2' if we
-                                // backtrack.  In this case, we need to push something on the stack, since back2 pops.
-                                // However, in the case of ()+? or similar, this empty match may be legitimate, so push the text
-                                // position associated with that empty match.
-                                StackPush(oldMarkPos);
-                                TrackPush2(StackPeek()); // Save old mark
+                                // The inner expression found an empty match. We'll go directly to BacktrackingSecond
+                                // if we backtrack. We do not touch the grouping stack here... instead, we record the
+                                // old mark and a "no-stack-pop" flag (0) on the backtracking stack.
+                                TrackPush2(oldMarkPos, 0);
                             }
                         }
                         advance = 1;
@@ -541,7 +539,11 @@ private bool TryMatchAtCurrentPosition(ReadOnlySpan<char> inputSpan)
                             // fails, we go to Lazybranchmark | RegexOpcode.Back2
                             TrackPop(2);
                             int pos = TrackPeek(1);
-                            TrackPush2(TrackPeek()); // Save old mark
+
+                            // Store the previous mark. The second value (1) flags that a grouping stack frame
+                            // must be popped when backtracking, because a new frame will be pushed next.
+                            TrackPush2(TrackPeek(), 1);
+
                             StackPush(pos);          // Make new mark
                             runtextpos = pos;        // Recall position
                             Goto(Operand(0));        // Loop
@@ -551,9 +553,17 @@ private bool TryMatchAtCurrentPosition(ReadOnlySpan<char> inputSpan)
                     case RegexOpcode.Lazybranchmark | RegexOpcode.BacktrackingSecond:
                         // The lazy loop has failed.  We'll do a true backtrack and
                         // start over before the lazy loop.
-                        StackPop();
-                        TrackPop();
-                        StackPush(TrackPeek()); // Recall old mark
+                        int needsPop = runtrack![runtrackpos]; // flag: 0 or 1
+                        int oldMark = runtrack[runtrackpos + 1]; // saved old mark
+                        runtrackpos += 2; // consume both payload ints
+                        if (needsPop != 0)
+                        {
+                            // We pushed on the grouping stack in the Backtracking arm; balance it now.
+                            StackPop();
+                        }
+
+                        // Restore the old mark and backtrack
+                        StackPush(oldMark);
                         break;
 
                     case RegexOpcode.Setcount:
diff --git a/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.Match.Tests.cs b/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.Match.Tests.cs
index 01553e0659b850..f7f60f1e1ecb04 100644
--- a/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.Match.Tests.cs
+++ b/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.Match.Tests.cs
@@ -329,6 +329,26 @@ public static IEnumerable<object[]> Match_MemberData()
             yield return (@"(b|a|aa)((?:aa)+?)+?$", "aaaaaaaa", RegexOptions.None, 0, 8, true, "aaaaaaaa");
             yield return (@"(|a|aa)(((?:aa)+?)+?|aaaaab)\w$", "aaaaaabc", RegexOptions.None, 0, 8, true, "aaaaaabc");
 
+            // Lazy loops with empty matches
+            if (!PlatformDetection.IsNetFramework)
+            {
+                // Fails on .NET Framework: https://github.com/dotnet/runtime/issues/111051
+                yield return (@"(.)+()+?b", "xyzb", RegexOptions.None, 0, 4, true, "xyzb");
+                yield return (@"^(.)+()+?b", "xyzb", RegexOptions.None, 0, 4, true, "xyzb");
+
+                if (!RegexHelpers.IsNonBacktracking(engine))
+                {
+                    // Fails on .NET Framework: https://github.com/dotnet/runtime/issues/58786
+                    yield return (@"(?<!a*(?:a?)+?)", @"x", RegexOptions.None, 0, 1, false, "");
+
+                    // Fails on .NET Framework: https://github.com/dotnet/runtime/issues/114626
+                    yield return (@"(?>(-*)+?-*)$", "abc", RegexOptions.None, 0, 3, true, "");
+
+                    // Fails on .NET Framework: https://github.com/dotnet/runtime/issues/63385
+                    yield return (@"(^+?)?()", "1", RegexOptions.None, 0, 1, true, "");
+                }
+            }
+
             // Nested loops
             yield return (@"(abcd*)+e", "abcde", RegexOptions.None, 0, 5, true, "abcde");
             yield return (@"(abcd*?)+e", "abcde", RegexOptions.None, 0, 5, true, "abcde");
diff --git a/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.MultipleMatches.Tests.cs b/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.MultipleMatches.Tests.cs
index ab5f20f413104d..cf3890fede1fe2 100644
--- a/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.MultipleMatches.Tests.cs
+++ b/src/libraries/System.Text.RegularExpressions/tests/FunctionalTests/Regex.MultipleMatches.Tests.cs
@@ -452,9 +452,18 @@ public static IEnumerable<object[]> Matches_TestData()
                             new CaptureData("x", 3, 1),
                         }
                     };
+
+                    // Fails on .NET Framework: https://github.com/dotnet/runtime/issues/111051
+                    yield return new object[]
+                    {
+                        engine, @"anyexpress1(?<=(.(any express|(any express)*)+?)anyexpress1)", "anystring anyexpress1", RegexOptions.None, new[]
+                        {
+                            new CaptureData("anyexpress1", 10, 11),
+                        }
+                    };
                 }
 
-                // Fails on .NET Framework: [ActiveIssue("https://github.com/dotnet/runtime/issues/62094")]
+                // Fails on .NET Framework: https://github.com/dotnet/runtime/issues/62094
                 yield return new object[]
                 {
                     engine, @"(?:){93}", "x", RegexOptions.None, new[]
@@ -463,6 +472,16 @@ public static IEnumerable<object[]> Matches_TestData()
                         new CaptureData("", 1, 0)
                     }
                 };
+
+                // Fails on .NET Framework: https://github.com/dotnet/runtime/issues/43314
+                yield return new object[]
+                {
+                    engine, @"(?:(?:0?)+?(?:a?)+?)?", "0a", RegexOptions.None, new[]
+                    {
+                        new CaptureData("0a", 0, 2),
+                        new CaptureData("", 2, 0),
+                    }
+                };
 #endif
             }
         }