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 859c41b6c34988..45ea2d6e6e83e3 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
@@ -790,6 +790,11 @@ private RegexNode ReduceAtomic()
                             start = endExclusive;
                         }
 
+                        // Force a re-reduction if we know we've exposed new opportunities that'll be handled.
+                        reordered |=
+                            child.ChildCount() == 2 &&
+                            (child.Child(0).Kind is RegexNodeKind.Empty || child.Child(1).Kind is RegexNodeKind.Empty); // can be transformed into a ? or ??
+
                         // If anything was reordered, there may be new optimization opportunities inside
                         // of the alternation, so reduce it again.
                         if (reordered)
@@ -1032,6 +1037,22 @@ private RegexNode ReduceAlternation()
                             if (node.Kind == RegexNodeKind.Alternate)
                             {
                                 node = RemoveRedundantEmptiesAndNothings(node);
+
+                                // If the alternation is actually just a ? or ?? in disguise, transform it accordingly.
+                                //     (a|) becomes a?
+                                //     (|a) becomes a??
+                                // Such "optional" nodes are processed more efficiently, including being able to be better coalesced with surrounding nodes.
+                                if (node.Kind is RegexNodeKind.Alternate && node.ChildCount() == 2)
+                                {
+                                    if (node.Child(1).Kind is RegexNodeKind.Empty)
+                                    {
+                                        node = node.Child(0).MakeQuantifier(lazy: false, min: 0, max: 1);
+                                    }
+                                    else if (node.Child(0).Kind is RegexNodeKind.Empty)
+                                    {
+                                        node = node.Child(1).MakeQuantifier(lazy: true, min: 0, max: 1);
+                                    }
+                                }
                             }
                         }
                     }
diff --git a/src/libraries/System.Text.RegularExpressions/tests/UnitTests/RegexReductionTests.cs b/src/libraries/System.Text.RegularExpressions/tests/UnitTests/RegexReductionTests.cs
index 226f9c3be4d50f..8cbf120e660186 100644
--- a/src/libraries/System.Text.RegularExpressions/tests/UnitTests/RegexReductionTests.cs
+++ b/src/libraries/System.Text.RegularExpressions/tests/UnitTests/RegexReductionTests.cs
@@ -306,6 +306,12 @@ public class RegexReductionTests
         [InlineData("abcd|aefg", "a(?>bcd|efg)")]
         [InlineData("abcd|abc|ab|a", "a(?>bcd|bc|b|)")]
         [InlineData("^abcd|^abce", "^(?:abc[de])")]
+        [InlineData("abc|", "(?:abc)?")]
+        [InlineData("a|", "a?")]
+        [InlineData("(?:abc|)d", "(?>(?:abc)?)d")]
+        [InlineData("(?:a|)a", "a{1,2}")]
+        [InlineData("(?:a|)a*", "a*")]
+        [InlineData("a+(?:a|)", "a+")]
         // [InlineData("abcde|abcdef", "abcde(?>|f)")] // TODO https://github.com/dotnet/runtime/issues/66031: Need to reorganize optimizations to avoid an extra Empty being left at the end of the tree
         [InlineData("abcdef|abcde", "abcde(?>f|)")]
         [InlineData("abcdef|abcdeg|abcdeh|abcdei|abcdej|abcdek|abcdel", "abcde[f-l]")]