diff --git a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexNode.cs b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexNode.cs
index 05cd639bd3dfe2..496e6d368bd5fc 100644
--- a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexNode.cs
+++ b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexNode.cs
@@ -2086,23 +2086,42 @@ static bool RemoveCaptures(RegexNode parent, int nodeIndex)
             // eliminate any ending backtracking from it.
             EliminateEndingBacktracking();
 
-            // A positive lookaround wrapped around an empty is a nop, and we can reduce it
-            // to simply Empty.  A developer typically doesn't write this, but rather it evolves
-            // due to optimizations resulting in empty.
-
-            // A negative lookaround wrapped around an empty child, i.e. (?!), is
-            // sometimes used as a way to insert a guaranteed no-match into the expression,
-            // often as part of a conditional. We can reduce it to simply Nothing.
+            RegexNode child = Child(0);
 
-            if (Child(0).Kind == RegexNodeKind.Empty)
+            // A positive lookahead that wraps a zero-width assertion is useless wrapping and can be removed.
+            // Similarly, a positive lookaround wrapped around an empty can be reduced simply to Empty.
+            // A developer typically doesn't write this, but rather it evolves due to optimizations resulting in empty.
+            if (Kind is RegexNodeKind.PositiveLookaround)
             {
-                Kind = Kind == RegexNodeKind.PositiveLookaround ? RegexNodeKind.Empty : RegexNodeKind.Nothing;
-                Children = null;
+                if (((Options & RegexOptions.RightToLeft) == 0 && IsZeroWidthAssertion(child.Kind)) ||
+                    child.Kind is RegexNodeKind.Empty)
+                {
+                    return child;
+                }
+            }
+            else if (Kind is RegexNodeKind.NegativeLookaround)
+            {
+                // A negative lookaround wrapped around an empty child, i.e. (?!), is
+                // sometimes used as a way to insert a guaranteed no-match into the expression,
+                // often as part of a conditional. We can reduce it to simply Nothing.
+                if (child.Kind is RegexNodeKind.Empty)
+                {
+                    Kind = RegexNodeKind.Nothing;
+                    Children = null;
+                }
             }
 
             return this;
         }
 
+        private static bool IsZeroWidthAssertion(RegexNodeKind kind) => kind is
+            RegexNodeKind.PositiveLookaround or RegexNodeKind.NegativeLookaround or
+            RegexNodeKind.Beginning or RegexNodeKind.Start or
+            RegexNodeKind.Bol or RegexNodeKind.Eol or
+            RegexNodeKind.End or RegexNodeKind.EndZ or
+            RegexNodeKind.Boundary or RegexNodeKind.ECMABoundary or
+            RegexNodeKind.NonBoundary or RegexNodeKind.NonECMABoundary;
+
         /// <summary>Gets whether the node contains a backreference anywhere in its tree.</summary>
         private static bool? ContainsBackreference(RegexNode node)
         {
diff --git a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexPrefixAnalyzer.cs b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexPrefixAnalyzer.cs
index 93ab67a2c392a0..34e5a84c85a5da 100644
--- a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexPrefixAnalyzer.cs
+++ b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/RegexPrefixAnalyzer.cs
@@ -1354,8 +1354,6 @@ private static RegexNodeKind FindLeadingOrTrailingAnchor(RegexNode node, bool le
                     case RegexNodeKind.Start:
                     case RegexNodeKind.EndZ:
                     case RegexNodeKind.End:
-                    case RegexNodeKind.Boundary:
-                    case RegexNodeKind.ECMABoundary:
                         // Return any anchor found.
                         return node.Kind;
 
@@ -1389,6 +1387,7 @@ private static RegexNodeKind FindLeadingOrTrailingAnchor(RegexNode node, bool le
                                     {
                                         case RegexNodeKind.Empty or RegexNodeKind.NegativeLookaround:
                                         case RegexNodeKind.PositiveLookaround when ((node.Options | tmpChild.Options) & RegexOptions.RightToLeft) != 0:
+                                        case RegexNodeKind.Boundary or RegexNodeKind.ECMABoundary or RegexNodeKind.NonBoundary or RegexNodeKind.NonECMABoundary:
                                             // Skip over zero-width assertions.
                                             continue;
 
diff --git a/src/libraries/System.Text.RegularExpressions/tests/UnitTests/RegexFindOptimizationsTests.cs b/src/libraries/System.Text.RegularExpressions/tests/UnitTests/RegexFindOptimizationsTests.cs
index 8501700b31c180..856f3d85d52627 100644
--- a/src/libraries/System.Text.RegularExpressions/tests/UnitTests/RegexFindOptimizationsTests.cs
+++ b/src/libraries/System.Text.RegularExpressions/tests/UnitTests/RegexFindOptimizationsTests.cs
@@ -34,7 +34,7 @@ public class RegexFindOptimizationsTests
         [InlineData(@"(?=^)abc", 0, (int)FindNextStartingPositionMode.LeadingAnchor_LeftToRight_Beginning)]
         [InlineData(@"(?=.*$)abc", 0, (int)FindNextStartingPositionMode.LeadingString_LeftToRight)]
         [InlineData(@"(?=^)abc", (int)RegexOptions.RightToLeft, (int)FindNextStartingPositionMode.LeadingString_RightToLeft)]
-        [InlineData(@"abc(?=^)", (int)RegexOptions.RightToLeft, (int)FindNextStartingPositionMode.LeadingString_RightToLeft)]
+        [InlineData(@"abc(?=^)", (int)RegexOptions.RightToLeft, (int)FindNextStartingPositionMode.LeadingAnchor_RightToLeft_Beginning)]
         [InlineData(@"(?<!42)(?=^)abc", 0, (int)FindNextStartingPositionMode.LeadingAnchor_LeftToRight_Beginning)]
         [InlineData(@"(?<=^)abc", 0, (int)FindNextStartingPositionMode.LeadingString_LeftToRight)]
         [InlineData(@"(?<=^)(?=^)abc", 0, (int)FindNextStartingPositionMode.LeadingAnchor_LeftToRight_Beginning)]
diff --git a/src/libraries/System.Text.RegularExpressions/tests/UnitTests/RegexReductionTests.cs b/src/libraries/System.Text.RegularExpressions/tests/UnitTests/RegexReductionTests.cs
index 1c0ba4031f076b..361b8ec191da44 100644
--- a/src/libraries/System.Text.RegularExpressions/tests/UnitTests/RegexReductionTests.cs
+++ b/src/libraries/System.Text.RegularExpressions/tests/UnitTests/RegexReductionTests.cs
@@ -403,6 +403,16 @@ public class RegexReductionTests
         [InlineData(@"\z\z", @"\z")]
         [InlineData(@"\G\G", @"\G")]
         [InlineData(@"\A\A", @"\A")]
+        // Lookarounds
+        [InlineData(@"(?=^)abc", @"^abc")]
+        [InlineData(@"(?=\G)abc", @"\Gabc")]
+        [InlineData(@"abc(?=$)", @"abc$")]
+        [InlineData(@"(?=\b)abc", @"\babc")]
+        [InlineData(@"abc(?=\z)", @"abc\z")]
+        [InlineData(@"abc(?=\Z)", @"abc\Z")]
+        [InlineData(@"abc(?=\A)", @"abc\A")]
+        [InlineData(@"(?=(?=(?=abc)))", @"(?=abc)")]
+        [InlineData(@"(?=(?<=(?=abc)))", @"(?<=(?=abc))")]
         // Nothing handling
         [InlineData(@"\wabc(?!)def", "(?!)")]
         [InlineData(@"\wabc(?!)def|ghi(?!)", "(?!)")]