diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 72d7f692f9b43..754b82a39c8d9 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -1254,9 +1254,10 @@ export const enum CheckMode {
     Inferential = 1 << 1,                           // Inferential typing
     SkipContextSensitive = 1 << 2,                  // Skip context sensitive function expressions
     SkipGenericFunctions = 1 << 3,                  // Skip single signature generic functions
-    IsForSignatureHelp = 1 << 4,                    // Call resolution for purposes of signature help
-    IsForStringLiteralArgumentCompletions = 1 << 5, // Do not infer from the argument currently being typed
-    RestBindingElement = 1 << 6,                    // Checking a type that is going to be used to determine the type of a rest binding element
+    SkipAddingIntraExpressionSites = 1 << 4,        // Skip adding intra expression sites in nested expressions since only the outermost one has to be added
+    IsForSignatureHelp = 1 << 5,                    // Call resolution for purposes of signature help
+    IsForStringLiteralArgumentCompletions = 1 << 6, // Do not infer from the argument currently being typed
+    RestBindingElement = 1 << 7,                    // Checking a type that is going to be used to determine the type of a rest binding element
                                                     //   e.g. in `const { a, ...rest } = foo`, when checking the type of `foo` to determine the type of `rest`,
                                                     //   we need to preserve generic types instead of substituting them for constraints
     TypeOnly = 1 << 7,                              // Called from getTypeOfExpression, diagnostics may be omitted
@@ -29979,10 +29980,13 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                 elementFlags.push(ElementFlags.Optional);
             }
             else {
-                const type = checkExpressionForMutableLocation(e, checkMode, forceTuple);
+                const shouldAddAsIntraExpressionInferenceSite = inTupleContext && checkMode && checkMode & CheckMode.Inferential && !(checkMode & (CheckMode.SkipContextSensitive | CheckMode.SkipAddingIntraExpressionSites)) && isContextSensitive(e);
+                const elementCheckMode = (checkMode || CheckMode.Normal) | (shouldAddAsIntraExpressionInferenceSite ? CheckMode.SkipAddingIntraExpressionSites : 0);
+
+                const type = checkExpressionForMutableLocation(e, elementCheckMode, forceTuple);
                 elementTypes.push(addOptionality(type, /*isProperty*/ true, hasOmittedExpression));
                 elementFlags.push(hasOmittedExpression ? ElementFlags.Optional : ElementFlags.Required);
-                if (inTupleContext && checkMode && checkMode & CheckMode.Inferential && !(checkMode & CheckMode.SkipContextSensitive) && isContextSensitive(e)) {
+                if (shouldAddAsIntraExpressionInferenceSite) {
                     const inferenceContext = getInferenceContext(node);
                     Debug.assert(inferenceContext);  // In CheckMode.Inferential we should always have an inference context
                     addIntraExpressionInferenceSite(inferenceContext, e, type);
@@ -30147,12 +30151,17 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             if (memberDecl.kind === SyntaxKind.PropertyAssignment ||
                 memberDecl.kind === SyntaxKind.ShorthandPropertyAssignment ||
                 isObjectLiteralMethod(memberDecl)) {
-                let type = memberDecl.kind === SyntaxKind.PropertyAssignment ? checkPropertyAssignment(memberDecl, checkMode) :
+
+                const shouldAddAsIntraExpressionInferenceSite = contextualType && checkMode & CheckMode.Inferential && !(checkMode & (CheckMode.SkipContextSensitive | CheckMode.SkipAddingIntraExpressionSites)) &&
+                    (memberDecl.kind === SyntaxKind.PropertyAssignment || memberDecl.kind === SyntaxKind.MethodDeclaration) && isContextSensitive(memberDecl);
+                const propCheckMode = checkMode | (shouldAddAsIntraExpressionInferenceSite ? CheckMode.SkipAddingIntraExpressionSites : 0);
+
+                let type = memberDecl.kind === SyntaxKind.PropertyAssignment ? checkPropertyAssignment(memberDecl, propCheckMode) :
                     // avoid resolving the left side of the ShorthandPropertyAssignment outside of the destructuring
                     // for error recovery purposes. For example, if a user wrote `{ a = 100 }` instead of `{ a: 100 }`.
                     // we don't want to say "could not find 'a'".
-                    memberDecl.kind === SyntaxKind.ShorthandPropertyAssignment ? checkExpressionForMutableLocation(!inDestructuringPattern && memberDecl.objectAssignmentInitializer ? memberDecl.objectAssignmentInitializer : memberDecl.name, checkMode) :
-                    checkObjectLiteralMethod(memberDecl, checkMode);
+                    memberDecl.kind === SyntaxKind.ShorthandPropertyAssignment ? checkExpressionForMutableLocation(!inDestructuringPattern && memberDecl.objectAssignmentInitializer ? memberDecl.objectAssignmentInitializer : memberDecl.name, propCheckMode) :
+                    checkObjectLiteralMethod(memberDecl, propCheckMode);
                 if (isInJavascript) {
                     const jsDocType = getTypeForDeclarationFromJSDocComment(memberDecl);
                     if (jsDocType) {
@@ -30207,8 +30216,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                 member = prop;
                 allPropertiesTable?.set(prop.escapedName, prop);
 
-                if (contextualType && checkMode & CheckMode.Inferential && !(checkMode & CheckMode.SkipContextSensitive) &&
-                    (memberDecl.kind === SyntaxKind.PropertyAssignment || memberDecl.kind === SyntaxKind.MethodDeclaration) && isContextSensitive(memberDecl)) {
+                if (shouldAddAsIntraExpressionInferenceSite) {
                     const inferenceContext = getInferenceContext(node);
                     Debug.assert(inferenceContext);  // In CheckMode.Inferential we should always have an inference context
                     const inferenceNode = memberDecl.kind === SyntaxKind.PropertyAssignment ? memberDecl.initializer : memberDecl;
@@ -30442,7 +30450,10 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         for (const attributeDecl of attributes.properties) {
             const member = attributeDecl.symbol;
             if (isJsxAttribute(attributeDecl)) {
-                const exprType = checkJsxAttribute(attributeDecl, checkMode);
+                const shouldAddAsIntraExpressionInferenceSite = contextualType && checkMode & CheckMode.Inferential && !(checkMode & (CheckMode.SkipContextSensitive | CheckMode.SkipAddingIntraExpressionSites)) && isContextSensitive(attributeDecl);
+                const attributeCheckMode = checkMode | (shouldAddAsIntraExpressionInferenceSite ? CheckMode.SkipAddingIntraExpressionSites : 0);
+
+                const exprType = checkJsxAttribute(attributeDecl, attributeCheckMode);
                 objectFlags |= getObjectFlags(exprType) & ObjectFlags.PropagatingFlags;
 
                 const attributeSymbol = createSymbol(SymbolFlags.Property | member.flags, member.escapedName);
@@ -30464,7 +30475,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                         addDeprecatedSuggestion(attributeDecl.name, prop.declarations, attributeDecl.name.escapedText as string);
                     }
                 }
-                if (contextualType && checkMode & CheckMode.Inferential && !(checkMode & CheckMode.SkipContextSensitive) && isContextSensitive(attributeDecl)) {
+                if (shouldAddAsIntraExpressionInferenceSite) {
                     const inferenceContext = getInferenceContext(attributes);
                     Debug.assert(inferenceContext);  // In CheckMode.Inferential we should always have an inference context
                     const inferenceNode = (attributeDecl.initializer as JsxExpression).expression!;