diff --git a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/Symbolic/CharKind.cs b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/Symbolic/CharKind.cs
index 39f95920da31b3..1952a7dcd1e006 100644
--- a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/Symbolic/CharKind.cs
+++ b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/Symbolic/CharKind.cs
@@ -29,9 +29,12 @@ internal static class CharKind
         /// <summary>Gets the next character kind from a context</summary>
         internal static uint Next(uint context) => context >> 3;
 
-        /// <summary>Creates the context of the previous and the next character kinds.</summary>
+        /// <summary>Encodes the pair (prevKind, nextKind) using 6 bits</summary>
         internal static uint Context(uint prevKind, uint nextKind) => (nextKind << 3) | prevKind;
 
+        /// <summary>Exclusive maximum context (limit) is 64 because a context uses bit-shifting where each kind needs 3 bits.</summary>
+        internal const int ContextLimit = 64;
+
         internal static string DescribePrev(uint i) => i switch
         {
             StartStop => @"\A",
diff --git a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/Symbolic/SymbolicRegexMatcher.cs b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/Symbolic/SymbolicRegexMatcher.cs
index ac56fd972d0cf1..a8cec12036225a 100644
--- a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/Symbolic/SymbolicRegexMatcher.cs
+++ b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/Symbolic/SymbolicRegexMatcher.cs
@@ -359,9 +359,7 @@ public DfaMatchingState<TSetType> TakeTransition(
                 Debug.Assert(builder._delta is not null);
 
                 int offset = (currentState.Id << builder._mintermsCount) | mintermId;
-                return
-                    builder._delta[offset] ??
-                    matcher.CreateNewTransition(currentState, minterm, offset);
+                return Volatile.Read(ref builder._delta[offset]) ?? matcher.CreateNewTransition(currentState, minterm, offset);
             }
         }
 
@@ -391,7 +389,7 @@ public DfaMatchingState<TSetType> TakeTransition(
                     DfaMatchingState<TSetType> nextStates = builder.MkState(oneState, currentStates.PrevCharKind);
 
                     int offset = (nextStates.Id << builder._mintermsCount) | mintermId;
-                    DfaMatchingState<TSetType> p = builder._delta[offset] ?? matcher.CreateNewTransition(nextStates, minterm, offset);
+                    DfaMatchingState<TSetType> p = Volatile.Read(ref builder._delta[offset]) ?? matcher.CreateNewTransition(nextStates, minterm, offset);
 
                     // Observe that if p.Node is an Or it will be flattened.
                     union = builder.MkOr2(union, p.Node);
diff --git a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/Symbolic/SymbolicRegexNode.cs b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/Symbolic/SymbolicRegexNode.cs
index 41dfdf3898bf58..bf46baf57c147e 100644
--- a/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/Symbolic/SymbolicRegexNode.cs
+++ b/src/libraries/System.Text.RegularExpressions/src/System/Text/RegularExpressions/Symbolic/SymbolicRegexNode.cs
@@ -13,6 +13,12 @@ namespace System.Text.RegularExpressions.Symbolic
     internal sealed class SymbolicRegexNode<S> where S : notnull
     {
         internal const string EmptyCharClass = "[]";
+        /// <summary>Some byte other than 0 to represent true</summary>
+        internal const byte TrueByte = 1;
+        /// <summary>Some byte other than 0 to represent false</summary>
+        internal const byte FalseByte = 2;
+        /// <summary>The undefined value is the default value 0</summary>
+        internal const byte UndefinedByte = 0;
 
         internal readonly SymbolicRegexBuilder<S> _builder;
         internal readonly SymbolicRegexKind _kind;
@@ -23,7 +29,11 @@ internal sealed class SymbolicRegexNode<S> where S : notnull
         internal readonly SymbolicRegexNode<S>? _right;
         internal readonly SymbolicRegexSet<S>? _alts;
 
-        private Dictionary<uint, bool>? _nullabilityCache;
+        /// <summary>
+        /// Caches nullability of this node for any given context (0 &lt;= context &lt; ContextLimit)
+        /// when _info.StartsWithSomeAnchor and _info.CanBeNullable are true. Otherwise the cache is null.
+        /// </summary>
+        private byte[]? _nullabilityCache;
 
         private S _startSet;
 
@@ -50,6 +60,7 @@ private SymbolicRegexNode(SymbolicRegexBuilder<S> builder, SymbolicRegexKind kin
             _info = info;
             _hashcode = ComputeHashCode();
             _startSet = ComputeStartSet();
+            _nullabilityCache = info.StartsWithSomeAnchor && info.CanBeNullable ? new byte[CharKind.ContextLimit] : null;
         }
 
         private bool _isInternalizedUnion;
@@ -162,92 +173,100 @@ static void AppendToList(SymbolicRegexNode<S> concat, List<SymbolicRegexNode<S>>
         /// <param name="context">kind info for previous and next characters</param>
         internal bool IsNullableFor(uint context)
         {
-            if (!_info.StartsWithSomeAnchor)
-                return IsNullable;
-
-            if (!_info.CanBeNullable)
-                return false;
+            if (_nullabilityCache is null)
+            {
+                // if _nullabilityCache is null then IsNullable==CanBeNullable
+                // Observe that if IsNullable==true then CanBeNullable==true.
+                // but when the node does not start with an anchor
+                // and IsNullable==false then CanBeNullable==false.
+                return _info.IsNullable;
+            }
 
             if (!StackHelper.TryEnsureSufficientExecutionStack())
             {
                 return StackHelper.CallOnEmptyStack(IsNullableFor, context);
             }
 
-            // Initialize the nullability cache for this node.
-            _nullabilityCache ??= new Dictionary<uint, bool>();
+            Debug.Assert(context < CharKind.ContextLimit);
 
-            if (!_nullabilityCache.TryGetValue(context, out bool is_nullable))
+            // If nullablity has been computed for the given context then return it
+            byte b = Volatile.Read(ref _nullabilityCache[context]);
+            if (b != UndefinedByte)
             {
-                switch (_kind)
-                {
-                    case SymbolicRegexKind.Loop:
-                        Debug.Assert(_left is not null);
-                        is_nullable = _lower == 0 || _left.IsNullableFor(context);
-                        break;
+                return b == TrueByte;
+            }
 
-                    case SymbolicRegexKind.Concat:
-                        Debug.Assert(_left is not null && _right is not null);
-                        is_nullable = _left.IsNullableFor(context) && _right.IsNullableFor(context);
-                        break;
+            // Otherwise compute the nullability recursively for the given context
+            bool is_nullable;
+            switch (_kind)
+            {
+                case SymbolicRegexKind.Loop:
+                    Debug.Assert(_left is not null);
+                    is_nullable = _lower == 0 || _left.IsNullableFor(context);
+                    break;
 
-                    case SymbolicRegexKind.Or:
-                    case SymbolicRegexKind.And:
-                        Debug.Assert(_alts is not null);
-                        is_nullable = _alts.IsNullableFor(context);
-                        break;
+                case SymbolicRegexKind.Concat:
+                    Debug.Assert(_left is not null && _right is not null);
+                    is_nullable = _left.IsNullableFor(context) && _right.IsNullableFor(context);
+                    break;
 
-                    case SymbolicRegexKind.Not:
-                        Debug.Assert(_left is not null);
-                        is_nullable = !_left.IsNullableFor(context);
-                        break;
+                case SymbolicRegexKind.Or:
+                case SymbolicRegexKind.And:
+                    Debug.Assert(_alts is not null);
+                    is_nullable = _alts.IsNullableFor(context);
+                    break;
 
-                    case SymbolicRegexKind.StartAnchor:
-                        is_nullable = CharKind.Prev(context) == CharKind.StartStop;
-                        break;
+                case SymbolicRegexKind.Not:
+                    Debug.Assert(_left is not null);
+                    is_nullable = !_left.IsNullableFor(context);
+                    break;
 
-                    case SymbolicRegexKind.EndAnchor:
-                        is_nullable = CharKind.Next(context) == CharKind.StartStop;
-                        break;
+                case SymbolicRegexKind.StartAnchor:
+                    is_nullable = CharKind.Prev(context) == CharKind.StartStop;
+                    break;
 
-                    case SymbolicRegexKind.BOLAnchor:
-                        // Beg-Of-Line anchor is nullable when the previous character is Newline or Start
-                        // note: at least one of the bits must be 1, but both could also be 1 in case of very first newline
-                        is_nullable = (CharKind.Prev(context) & CharKind.NewLineS) != 0;
-                        break;
+                case SymbolicRegexKind.EndAnchor:
+                    is_nullable = CharKind.Next(context) == CharKind.StartStop;
+                    break;
 
-                    case SymbolicRegexKind.EOLAnchor:
-                        // End-Of-Line anchor is nullable when the next character is Newline or Stop
-                        // note: at least one of the bits must be 1, but both could also be 1 in case of \Z
-                        is_nullable = (CharKind.Next(context) & CharKind.NewLineS) != 0;
-                        break;
+                case SymbolicRegexKind.BOLAnchor:
+                    // Beg-Of-Line anchor is nullable when the previous character is Newline or Start
+                    // note: at least one of the bits must be 1, but both could also be 1 in case of very first newline
+                    is_nullable = (CharKind.Prev(context) & CharKind.NewLineS) != 0;
+                    break;
 
-                    case SymbolicRegexKind.WBAnchor:
-                        // test that prev char is word letter iff next is not not word letter
-                        is_nullable = ((CharKind.Prev(context) & CharKind.WordLetter) ^ (CharKind.Next(context) & CharKind.WordLetter)) != 0;
-                        break;
+                case SymbolicRegexKind.EOLAnchor:
+                    // End-Of-Line anchor is nullable when the next character is Newline or Stop
+                    // note: at least one of the bits must be 1, but both could also be 1 in case of \Z
+                    is_nullable = (CharKind.Next(context) & CharKind.NewLineS) != 0;
+                    break;
 
-                    case SymbolicRegexKind.NWBAnchor:
-                        // test that prev char is word letter iff next is word letter
-                        is_nullable = ((CharKind.Prev(context) & CharKind.WordLetter) ^ (CharKind.Next(context) & CharKind.WordLetter)) == 0;
-                        break;
+                case SymbolicRegexKind.WBAnchor:
+                    // test that prev char is word letter iff next is not not word letter
+                    is_nullable = ((CharKind.Prev(context) & CharKind.WordLetter) ^ (CharKind.Next(context) & CharKind.WordLetter)) != 0;
+                    break;
 
-                    case SymbolicRegexKind.EndAnchorZ:
-                        // \Z anchor is nullable when the next character is either the last Newline or Stop
-                        // note: CharKind.NewLineS == CharKind.Newline|CharKind.StartStop
-                        is_nullable = (CharKind.Next(context) & CharKind.StartStop) != 0;
-                        break;
+                case SymbolicRegexKind.NWBAnchor:
+                    // test that prev char is word letter iff next is word letter
+                    is_nullable = ((CharKind.Prev(context) & CharKind.WordLetter) ^ (CharKind.Next(context) & CharKind.WordLetter)) == 0;
+                    break;
 
-                    default: //SymbolicRegexKind.EndAnchorZRev:
-                        // EndAnchorZRev (rev(\Z)) anchor is nullable when the prev character is either the first Newline or Start
-                        // note: CharKind.NewLineS == CharKind.Newline|CharKind.StartStop
-                        Debug.Assert(_kind == SymbolicRegexKind.EndAnchorZRev);
-                        is_nullable = (CharKind.Prev(context) & CharKind.StartStop) != 0;
-                        break;
-                }
+                case SymbolicRegexKind.EndAnchorZ:
+                    // \Z anchor is nullable when the next character is either the last Newline or Stop
+                    // note: CharKind.NewLineS == CharKind.Newline|CharKind.StartStop
+                    is_nullable = (CharKind.Next(context) & CharKind.StartStop) != 0;
+                    break;
 
-                _nullabilityCache[context] = is_nullable;
+                default: // SymbolicRegexKind.EndAnchorZRev:
+                         // EndAnchorZRev (rev(\Z)) anchor is nullable when the prev character is either the first Newline or Start
+                         // note: CharKind.NewLineS == CharKind.Newline|CharKind.StartStop
+                    Debug.Assert(_kind == SymbolicRegexKind.EndAnchorZRev);
+                    is_nullable = (CharKind.Prev(context) & CharKind.StartStop) != 0;
+                    break;
             }
 
+            Volatile.Write(ref _nullabilityCache[context], is_nullable ? TrueByte : FalseByte);
+
             return is_nullable;
         }
 
diff --git a/src/libraries/System.Text.RegularExpressions/tests/Regex.Match.Tests.cs b/src/libraries/System.Text.RegularExpressions/tests/Regex.Match.Tests.cs
index 6dd56fc109e9b3..e7f0b4d2985538 100644
--- a/src/libraries/System.Text.RegularExpressions/tests/Regex.Match.Tests.cs
+++ b/src/libraries/System.Text.RegularExpressions/tests/Regex.Match.Tests.cs
@@ -1827,5 +1827,33 @@ public async Task UseRegexConcurrently_ThreadSafe_Success(RegexEngine engine, Ti
                              }, CancellationToken.None, TaskCreationOptions.LongRunning, TaskScheduler.Default)).ToArray());
             }
         }
+
+        [Theory]
+        [MemberData(nameof(MatchWordsInAnchoredRegexes_TestData))]
+        public async Task MatchWordsInAnchoredRegexes(RegexEngine engine, RegexOptions options, string pattern, string input, (int, int)[] matches)
+        {
+            // The aim of these test is to test corner cases of matches involving anchors
+            // For NonBacktracking these tests are meant to
+            // cover most contexts in _nullabilityForContext in SymbolicRegexNode
+            Regex r = await RegexHelpers.GetRegexAsync(engine, pattern, options);
+            MatchCollection ms = r.Matches(input);
+            Assert.Equal(matches.Length, ms.Count);
+            for (int i = 0; i < matches.Length; i++)
+            {
+                Assert.Equal(ms[i].Index, matches[i].Item1);
+                Assert.Equal(ms[i].Length, matches[i].Item2);
+            }
+        }
+
+        public static IEnumerable<object[]> MatchWordsInAnchoredRegexes_TestData()
+        {
+            foreach (RegexEngine engine in RegexHelpers.AvailableEngines)
+            {
+                yield return new object[] { engine, RegexOptions.None, @"\b\w{10,}\b", "this is a complicated word in a\nnontrivial sentence", new (int, int)[] { (10, 11), (32, 10) } };
+                yield return new object[] { engine, RegexOptions.Multiline, @"^\w{10,}\b", "this is a\ncomplicated word in a\nnontrivial sentence", new (int, int)[] { (10, 11), (32, 10) } };
+                yield return new object[] { engine, RegexOptions.None, @"\b\d{1,2}\/\d{1,2}\/\d{2,4}\b", "date 10/12/1966 and 10/12/66 are the same", new (int, int)[] { (5, 10), (20, 8) } };
+                yield return new object[] { engine, RegexOptions.Multiline, @"\b\d{1,2}\/\d{1,2}\/\d{2,4}$", "date 10/12/1966\nand 10/12/66\nare the same", new (int, int)[] { (5, 10), (20, 8) } };
+            }
+        }
     }
 }
diff --git a/src/libraries/System.Text.RegularExpressions/tests/RegexExperiment.cs b/src/libraries/System.Text.RegularExpressions/tests/RegexExperiment.cs
index 85d17ebc4dd486..ee6339561b8bc7 100644
--- a/src/libraries/System.Text.RegularExpressions/tests/RegexExperiment.cs
+++ b/src/libraries/System.Text.RegularExpressions/tests/RegexExperiment.cs
@@ -520,8 +520,9 @@ public void TestConjunctionOverCounting(string conjunct1, string conjunct2, stri
                 Assert.Contains("conditional", e.Message);
             }
         }
+        #endregion
 
-
+        #region Random input generation tests
         public static IEnumerable<object[]> GenerateRandomMembers_TestData()
         {
             string[] patterns = new string[] { @"pa[5\$s]{2}w[o0]rd$", @"\w\d+", @"\d{10}" };
@@ -536,7 +537,7 @@ public static IEnumerable<object[]> GenerateRandomMembers_TestData()
                     {
                         foreach (string input in inputs)
                         {
-                            yield return new object[] {engine, pattern, input, !negative };
+                            yield return new object[] { engine, pattern, input, !negative };
                         }
                     }
                 }