diff --git a/src/EditorFeatures/CSharpTest2/Recommendations/StackAllocKeywordRecommenderTests.cs b/src/EditorFeatures/CSharpTest2/Recommendations/StackAllocKeywordRecommenderTests.cs
index 3b7f050fb8d81ffff4dd7ed1ae2ad78985d9f75f..a006900dbfacfdc92c364bdcd022236435e8a61f 100644
--- a/src/EditorFeatures/CSharpTest2/Recommendations/StackAllocKeywordRecommenderTests.cs
+++ b/src/EditorFeatures/CSharpTest2/Recommendations/StackAllocKeywordRecommenderTests.cs
@@ -55,9 +55,9 @@ public async Task TestNotInEmptyStatement()
         }
 
         [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
-        public async Task TestNotInEmptySpace()
+        public async Task TestInEmptySpaceAfterAssignment()
         {
-            await VerifyAbsenceAsync(AddInsideMethod(
+            await VerifyKeywordAsync(AddInsideMethod(
 @"var v = $$"));
         }
 
@@ -71,9 +71,10 @@ public async Task TestInUnsafeEmptySpace()
         }
 
         [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
-        public async Task TestInUnsafeEmptySpace_NotAfterNonPointer()
+        public async Task TestInUnsafeEmptySpace_AfterNonPointer()
         {
-            await VerifyAbsenceAsync(
+            // There can be an implicit conversion to int
+            await VerifyKeywordAsync(
 @"unsafe class C {
     void Goo() {
       int v = $$");
@@ -124,12 +125,146 @@ unsafe static void Main(string[] args)
         [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
         public async Task TestInsideForStatementVarDecl3()
         {
-            await VerifyAbsenceAsync(
+            await VerifyKeywordAsync(
 @"class C
 {
     unsafe static void Main(string[] args)
     {
         for (string i = $$");
         }
+
+        [WorkItem(23584, "https://github.com/dotnet/roslyn/issues/23584")]
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        public async Task TestOnRHSOfAssignment_Span()
+        {
+            await VerifyKeywordAsync(AddInsideMethod(@"
+Span<int> s = $$"));
+        }
+
+        [WorkItem(23584, "https://github.com/dotnet/roslyn/issues/23584")]
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        public async Task TestOnRHSOfAssignment_Pointer()
+        {
+            await VerifyKeywordAsync(AddInsideMethod(
+@"int* v = $$"));
+        }
+
+        [WorkItem(23584, "https://github.com/dotnet/roslyn/issues/23584")]
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        public async Task TestOnRHSOfAssignment_ReAssignment()
+        {
+            await VerifyKeywordAsync(AddInsideMethod(
+@"v = $$"));
+        }
+
+        [WorkItem(23584, "https://github.com/dotnet/roslyn/issues/23584")]
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        public async Task TestOnRHSWithCast()
+        {
+            await VerifyKeywordAsync(AddInsideMethod(@"
+var s = (Span<char>)$$"));
+
+            await VerifyKeywordAsync(AddInsideMethod(@"
+s = (Span<char>)$$"));
+        }
+
+        [WorkItem(23584, "https://github.com/dotnet/roslyn/issues/23584")]
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        public async Task TestOnRHSWithConditionalExpression_True()
+        {
+            await VerifyKeywordAsync(AddInsideMethod(@"
+var s = value ? $$"));
+
+            await VerifyKeywordAsync(AddInsideMethod(@"
+s = value ? $$"));
+        }
+
+        [WorkItem(23584, "https://github.com/dotnet/roslyn/issues/23584")]
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        public async Task TestOnRHSWithConditionalExpression_True_WithCast()
+        {
+            await VerifyKeywordAsync(AddInsideMethod(@"
+var s = value ? (Span<int>)$$"));
+
+            await VerifyKeywordAsync(AddInsideMethod(@"
+s = value ? (Span<int>)$$"));
+        }
+
+        [WorkItem(23584, "https://github.com/dotnet/roslyn/issues/23584")]
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        public async Task TestOnRHSWithConditionalExpression_False()
+        {
+            await VerifyKeywordAsync(AddInsideMethod(@"
+var s = value ? stackalloc int[10] : $$"));
+
+            await VerifyKeywordAsync(AddInsideMethod(@"
+s = value ? stackalloc int[10] : $$"));
+        }
+
+        [WorkItem(23584, "https://github.com/dotnet/roslyn/issues/23584")]
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        public async Task TestOnRHSWithConditionalExpression_False_WithCast()
+        {
+            await VerifyKeywordAsync(AddInsideMethod(@"
+var s = value ? stackalloc int[10] : (Span<int>)$$"));
+
+            await VerifyKeywordAsync(AddInsideMethod(@"
+s = value ? stackalloc int[10] : (Span<int>)$$"));
+        }
+
+        [WorkItem(23584, "https://github.com/dotnet/roslyn/issues/23584")]
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        public async Task TestOnRHSWithConditionalExpression_NestedConditional_True()
+        {
+            await VerifyKeywordAsync(AddInsideMethod(@"
+var s = value1 ? value2 ? $$"));
+
+            await VerifyKeywordAsync(AddInsideMethod(@"
+s = value1 ? value2 ? $$"));
+        }
+
+        [WorkItem(23584, "https://github.com/dotnet/roslyn/issues/23584")]
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        public async Task TestOnRHSWithConditionalExpression_NestedConditional_WithCast_True()
+        {
+            await VerifyKeywordAsync(AddInsideMethod(@"
+var s = value1 ? value2 ? (Span<int>)$$"));
+
+            await VerifyKeywordAsync(AddInsideMethod(@"
+s = value1 ? value2 ? (Span<int>)$$"));
+        }
+
+        [WorkItem(23584, "https://github.com/dotnet/roslyn/issues/23584")]
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        public async Task TestOnRHSWithConditionalExpression_NestedConditional_False()
+        {
+            await VerifyKeywordAsync(AddInsideMethod(@"
+var s = value1 ? value2 ? stackalloc int [10] : $$"));
+
+            await VerifyKeywordAsync(AddInsideMethod(@"
+s = value1 ? value2 ? stackalloc int [10] : $$"));
+        }
+
+        [WorkItem(23584, "https://github.com/dotnet/roslyn/issues/23584")]
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        public async Task TestOnRHSWithConditionalExpression_NestedConditional_WithCast_False()
+        {
+            await VerifyKeywordAsync(AddInsideMethod(@"
+var s = value1 ? value2 ? stackalloc int [10] : (Span<int>)$$"));
+
+            await VerifyKeywordAsync(AddInsideMethod(@"
+s = value1 ? value2 ? stackalloc int [10] : (Span<int>)$$"));
+        }
+
+        [WorkItem(23584, "https://github.com/dotnet/roslyn/issues/23584")]
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        public async Task TestNotInLHSOfAssignment()
+        {
+            await VerifyAbsenceAsync(AddInsideMethod(@"
+var x $$ ="));
+
+            await VerifyAbsenceAsync(AddInsideMethod(@"
+x $$ ="));
+        }
     }
 }
diff --git a/src/Features/CSharp/Portable/Completion/KeywordRecommenders/StackAllocKeywordRecommender.cs b/src/Features/CSharp/Portable/Completion/KeywordRecommenders/StackAllocKeywordRecommender.cs
index 5a9cc3be3da999877a4fd45a49c8621a5e70a33f..a09924f881384d21364a8c5f9833b8789fd48687 100644
--- a/src/Features/CSharp/Portable/Completion/KeywordRecommenders/StackAllocKeywordRecommender.cs
+++ b/src/Features/CSharp/Portable/Completion/KeywordRecommenders/StackAllocKeywordRecommender.cs
@@ -16,20 +16,47 @@ public StackAllocKeywordRecommender()
 
         protected override bool IsValidContext(int position, CSharpSyntaxContext context, CancellationToken cancellationToken)
         {
-            // type t = |
-            var token = context.TargetToken;
-            if (token.IsUnsafeContext())
+            var node = context.TargetToken.Parent;
+
+            // At start of a file
+            if (node == null)
+            {
+                return false;
+            }
+
+            // After a cast or parenthesized expression: (Span<int>)stackalloc
+            if (context.TargetToken.IsAfterPossibleCast())
+            {
+                node = node.Parent;
+            }
+
+            // Inside a conditional expression: value ? stackalloc : stackalloc
+            while (node.IsKind(SyntaxKind.ConditionalExpression) &&
+                (context.TargetToken.IsKind(SyntaxKind.QuestionToken, SyntaxKind.ColonToken) || context.TargetToken.IsAfterPossibleCast()))
+            {
+                node = node.Parent;
+            }
+
+            // assignment: x = stackalloc
+            if (node.IsKind(SyntaxKind.SimpleAssignmentExpression))
+            {
+                return node.Parent.IsKind(SyntaxKind.ExpressionStatement);
+            }
+
+            // declaration: var x = stackalloc
+            if (node.IsKind(SyntaxKind.EqualsValueClause))
             {
-                if (token.Kind() == SyntaxKind.EqualsToken &&
-                    token.Parent.IsKind(SyntaxKind.EqualsValueClause) &&
-                    token.Parent.IsParentKind(SyntaxKind.VariableDeclarator) &&
-                    token.Parent.Parent.IsParentKind(SyntaxKind.VariableDeclaration))
+                node = node.Parent;
+
+                if (node.IsKind(SyntaxKind.VariableDeclarator))
                 {
-                    var variableDeclaration = (VariableDeclarationSyntax)token.Parent.Parent.Parent;
-                    if (variableDeclaration.IsParentKind(SyntaxKind.LocalDeclarationStatement) ||
-                        variableDeclaration.IsParentKind(SyntaxKind.ForStatement))
+                    node = node.Parent;
+
+                    if (node.IsKind(SyntaxKind.VariableDeclaration))
                     {
-                        return variableDeclaration.Type.IsVar || variableDeclaration.Type.IsKind(SyntaxKind.PointerType);
+                        node = node.Parent;
+
+                        return node.IsKind(SyntaxKind.LocalDeclarationStatement, SyntaxKind.ForStatement);
                     }
                 }
             }