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diff --git a/‎src/compiler/checker.ts
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+87-31Lines changed: 87 additions & 31 deletions b/‎src/compiler/checker.ts
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+87-31Lines changed: 87 additions & 31 deletions
diff --git a/‎src/compiler/types.ts
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+7Lines changed: 7 additions & 0 deletions b/‎src/compiler/types.ts
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+7Lines changed: 7 additions & 0 deletions
diff --git a/‎tests/baselines/reference/contextualTypingOfOptionalMembers.types
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+12-12Lines changed: 12 additions & 12 deletions b/‎tests/baselines/reference/contextualTypingOfOptionalMembers.types
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+12-12Lines changed: 12 additions & 12 deletions
@@ -21749,6 +21749,9 @@ namespace ts {
                 const inference = inferences[i];
                 if (t === inference.typeParameter) {
                     if (fix && !inference.isFixed) {
+                        // Before we commit to a particular inference (and thus lock out any further inferences),
+                        // we infer from any intra-expression inference sites we have collected.
+                        inferFromIntraExpressionSites(context);
                         clearCachedInferences(inferences);
                         inference.isFixed = true;
                     }
@@ -21766,6 +21769,37 @@ namespace ts {
             }
         }
 
+        function addIntraExpressionInferenceSite(context: InferenceContext, node: Expression | MethodDeclaration, type: Type) {
+            (context.intraExpressionInferenceSites ??= []).push({ node, type });
+        }
+
+        // We collect intra-expression inference sites within object and array literals to handle cases where
+        // inferred types flow between context sensitive element expressions. For example:
+        //
+        //   declare function foo<T>(arg: [(n: number) => T, (x: T) => void]): void;
+        //   foo([_a => 0, n => n.toFixed()]);
+        //
+        // Above, both arrow functions in the tuple argument are context sensitive, thus both are omitted from the
+        // pass that collects inferences from the non-context sensitive parts of the arguments. In the subsequent
+        // pass where nothing is omitted, we need to commit to an inference for T in order to contextually type the
+        // parameter in the second arrow function, but we want to first infer from the return type of the first
+        // arrow function. This happens automatically when the arrow functions are discrete arguments (because we
+        // infer from each argument before processing the next), but when the arrow functions are elements of an
+        // object or array literal, we need to perform intra-expression inferences early.
+        function inferFromIntraExpressionSites(context: InferenceContext) {
+            if (context.intraExpressionInferenceSites) {
+                for (const { node, type } of context.intraExpressionInferenceSites) {
+                    const contextualType = node.kind === SyntaxKind.MethodDeclaration ?
+                        getContextualTypeForObjectLiteralMethod(node as MethodDeclaration, ContextFlags.NoConstraints) :
+                        getContextualType(node, ContextFlags.NoConstraints);
+                    if (contextualType) {
+                        inferTypes(context.inferences, type, contextualType);
+                    }
+                }
+                context.intraExpressionInferenceSites = undefined;
+            }
+        }
+
         function createInferenceInfo(typeParameter: TypeParameter): InferenceInfo {
             return {
                 typeParameter,
@@ -27429,6 +27463,11 @@ namespace ts {
                     const type = checkExpressionForMutableLocation(e, checkMode, elementContextualType, forceTuple);
                     elementTypes.push(addOptionality(type, /*isProperty*/ true, hasOmittedExpression));
                     elementFlags.push(hasOmittedExpression ? ElementFlags.Optional : ElementFlags.Required);
+                    if (contextualType && someType(contextualType, isTupleLikeType) && checkMode && checkMode & CheckMode.Inferential && !(checkMode & CheckMode.SkipContextSensitive) && isContextSensitive(e)) {
+                        const inferenceContext = getInferenceContext(node);
+                        Debug.assert(inferenceContext);  // In CheckMode.Inferential we should always have an inference context
+                        addIntraExpressionInferenceSite(inferenceContext, e, type);
+                    }
                 }
             }
             if (inDestructuringPattern) {
@@ -27646,6 +27685,14 @@ namespace ts {
                     prop.target = member;
                     member = prop;
                     allPropertiesTable?.set(prop.escapedName, prop);
+
+                    if (contextualType && checkMode && checkMode & CheckMode.Inferential && !(checkMode & CheckMode.SkipContextSensitive) &&
+                        (memberDecl.kind === SyntaxKind.PropertyAssignment || memberDecl.kind === SyntaxKind.MethodDeclaration) && isContextSensitive(memberDecl)) {
+                        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;
+                        addIntraExpressionInferenceSite(inferenceContext, inferenceNode, type);
+                    }
                 }
                 else if (memberDecl.kind === SyntaxKind.SpreadAssignment) {
                     if (languageVersion < ScriptTarget.ES2015) {
@@ -29748,34 +29795,36 @@ namespace ts {
             if (node.kind !== SyntaxKind.Decorator) {
                 const contextualType = getContextualType(node, every(signature.typeParameters, p => !!getDefaultFromTypeParameter(p)) ? ContextFlags.SkipBindingPatterns : ContextFlags.None);
                 if (contextualType) {
-                    // We clone the inference context to avoid disturbing a resolution in progress for an
-                    // outer call expression. Effectively we just want a snapshot of whatever has been
-                    // inferred for any outer call expression so far.
-                    const outerContext = getInferenceContext(node);
-                    const outerMapper = getMapperFromContext(cloneInferenceContext(outerContext, InferenceFlags.NoDefault));
-                    const instantiatedType = instantiateType(contextualType, outerMapper);
-                    // If the contextual type is a generic function type with a single call signature, we
-                    // instantiate the type with its own type parameters and type arguments. This ensures that
-                    // the type parameters are not erased to type any during type inference such that they can
-                    // be inferred as actual types from the contextual type. For example:
-                    //   declare function arrayMap<T, U>(f: (x: T) => U): (a: T[]) => U[];
-                    //   const boxElements: <A>(a: A[]) => { value: A }[] = arrayMap(value => ({ value }));
-                    // Above, the type of the 'value' parameter is inferred to be 'A'.
-                    const contextualSignature = getSingleCallSignature(instantiatedType);
-                    const inferenceSourceType = contextualSignature && contextualSignature.typeParameters ?
-                        getOrCreateTypeFromSignature(getSignatureInstantiationWithoutFillingInTypeArguments(contextualSignature, contextualSignature.typeParameters)) :
-                        instantiatedType;
                     const inferenceTargetType = getReturnTypeOfSignature(signature);
-                    // Inferences made from return types have lower priority than all other inferences.
-                    inferTypes(context.inferences, inferenceSourceType, inferenceTargetType, InferencePriority.ReturnType);
-                    // Create a type mapper for instantiating generic contextual types using the inferences made
-                    // from the return type. We need a separate inference pass here because (a) instantiation of
-                    // the source type uses the outer context's return mapper (which excludes inferences made from
-                    // outer arguments), and (b) we don't want any further inferences going into this context.
-                    const returnContext = createInferenceContext(signature.typeParameters!, signature, context.flags);
-                    const returnSourceType = instantiateType(contextualType, outerContext && outerContext.returnMapper);
-                    inferTypes(returnContext.inferences, returnSourceType, inferenceTargetType);
-                    context.returnMapper = some(returnContext.inferences, hasInferenceCandidates) ? getMapperFromContext(cloneInferredPartOfContext(returnContext)) : undefined;
+                    if (couldContainTypeVariables(inferenceTargetType)) {
+                        // We clone the inference context to avoid disturbing a resolution in progress for an
+                        // outer call expression. Effectively we just want a snapshot of whatever has been
+                        // inferred for any outer call expression so far.
+                        const outerContext = getInferenceContext(node);
+                        const outerMapper = getMapperFromContext(cloneInferenceContext(outerContext, InferenceFlags.NoDefault));
+                        const instantiatedType = instantiateType(contextualType, outerMapper);
+                        // If the contextual type is a generic function type with a single call signature, we
+                        // instantiate the type with its own type parameters and type arguments. This ensures that
+                        // the type parameters are not erased to type any during type inference such that they can
+                        // be inferred as actual types from the contextual type. For example:
+                        //   declare function arrayMap<T, U>(f: (x: T) => U): (a: T[]) => U[];
+                        //   const boxElements: <A>(a: A[]) => { value: A }[] = arrayMap(value => ({ value }));
+                        // Above, the type of the 'value' parameter is inferred to be 'A'.
+                        const contextualSignature = getSingleCallSignature(instantiatedType);
+                        const inferenceSourceType = contextualSignature && contextualSignature.typeParameters ?
+                            getOrCreateTypeFromSignature(getSignatureInstantiationWithoutFillingInTypeArguments(contextualSignature, contextualSignature.typeParameters)) :
+                            instantiatedType;
+                        // Inferences made from return types have lower priority than all other inferences.
+                        inferTypes(context.inferences, inferenceSourceType, inferenceTargetType, InferencePriority.ReturnType);
+                        // Create a type mapper for instantiating generic contextual types using the inferences made
+                        // from the return type. We need a separate inference pass here because (a) instantiation of
+                        // the source type uses the outer context's return mapper (which excludes inferences made from
+                        // outer arguments), and (b) we don't want any further inferences going into this context.
+                        const returnContext = createInferenceContext(signature.typeParameters!, signature, context.flags);
+                        const returnSourceType = instantiateType(contextualType, outerContext && outerContext.returnMapper);
+                        inferTypes(returnContext.inferences, returnSourceType, inferenceTargetType);
+                        context.returnMapper = some(returnContext.inferences, hasInferenceCandidates) ? getMapperFromContext(cloneInferredPartOfContext(returnContext)) : undefined;
+                    }
                 }
             }
 
@@ -29789,7 +29838,7 @@ namespace ts {
             }
 
             const thisType = getThisTypeOfSignature(signature);
-            if (thisType) {
+            if (thisType && couldContainTypeVariables(thisType)) {
                 const thisArgumentNode = getThisArgumentOfCall(node);
                 inferTypes(context.inferences, getThisArgumentType(thisArgumentNode), thisType);
             }
@@ -29798,12 +29847,14 @@ namespace ts {
                 const arg = args[i];
                 if (arg.kind !== SyntaxKind.OmittedExpression && !(checkMode & CheckMode.IsForStringLiteralArgumentCompletions && hasSkipDirectInferenceFlag(arg))) {
                     const paramType = getTypeAtPosition(signature, i);
-                    const argType = checkExpressionWithContextualType(arg, paramType, context, checkMode);
-                    inferTypes(context.inferences, argType, paramType);
+                    if (couldContainTypeVariables(paramType)) {
+                        const argType = checkExpressionWithContextualType(arg, paramType, context, checkMode);
+                        inferTypes(context.inferences, argType, paramType);
+                    }
                 }
             }
 
-            if (restType) {
+            if (restType && couldContainTypeVariables(restType)) {
                 const spreadType = getSpreadArgumentType(args, argCount, args.length, restType, context, checkMode);
                 inferTypes(context.inferences, spreadType, restType);
             }
@@ -34162,6 +34213,11 @@ namespace ts {
                 context.contextualType = contextualType;
                 context.inferenceContext = inferenceContext;
                 const type = checkExpression(node, checkMode | CheckMode.Contextual | (inferenceContext ? CheckMode.Inferential : 0));
+                // In CheckMode.Inferential we collect intra-expression inference sites to process before fixing any type
+                // parameters. This information is no longer needed after the call to checkExpression.
+                if (inferenceContext && inferenceContext.intraExpressionInferenceSites) {
+                    inferenceContext.intraExpressionInferenceSites = undefined;
+                }
                 // We strip literal freshness when an appropriate contextual type is present such that contextually typed
                 // literals always preserve their literal types (otherwise they might widen during type inference). An alternative
                 // here would be to not mark contextually typed literals as fresh in the first place.
 
@@ -5915,6 +5915,13 @@ namespace ts {
         nonFixingMapper: TypeMapper;                  // Mapper that doesn't fix inferences
         returnMapper?: TypeMapper;                    // Type mapper for inferences from return types (if any)
         inferredTypeParameters?: readonly TypeParameter[]; // Inferred type parameters for function result
+        intraExpressionInferenceSites?: IntraExpressionInferenceSite[];
+    }
+
+    /* @internal */
+    export interface IntraExpressionInferenceSite {
+        node: Expression | MethodDeclaration;
+        type: Type;
     }
 
     /* @internal */
 
@@ -25,7 +25,7 @@ declare function app<State, Actions extends ActionsObject<State>>(obj: Options<S
 app({
 >app({    state: 100,    actions: {        foo: s => s // Should be typed number => number    },    view: (s, a) => undefined as any,}) : void
 >app : <State, Actions extends ActionsObject<State>>(obj: Options<State, Actions>) => void
->{    state: 100,    actions: {        foo: s => s // Should be typed number => number    },    view: (s, a) => undefined as any,} : { state: number; actions: { foo: (s: number) => number; }; view: (s: number, a: ActionsObject<number>) => any; }
+>{    state: 100,    actions: {        foo: s => s // Should be typed number => number    },    view: (s, a) => undefined as any,} : { state: number; actions: { foo: (s: number) => number; }; view: (s: number, a: { foo: (s: number) => number; }) => any; }
 
     state: 100,
 >state : number
@@ -43,10 +43,10 @@ app({
 
     },
     view: (s, a) => undefined as any,
->view : (s: number, a: ActionsObject<number>) => any
->(s, a) => undefined as any : (s: number, a: ActionsObject<number>) => any
+>view : (s: number, a: { foo: (s: number) => number; }) => any
+>(s, a) => undefined as any : (s: number, a: { foo: (s: number) => number; }) => any
 >s : number
->a : ActionsObject<number>
+>a : { foo: (s: number) => number; }
 >undefined as any : any
 >undefined : undefined
 
@@ -95,7 +95,7 @@ declare function app2<State, Actions extends ActionsObject<State>>(obj: Options2
 app2({
 >app2({    state: 100,    actions: {        foo: s => s // Should be typed number => number    },    view: (s, a) => undefined as any,}) : void
 >app2 : <State, Actions extends ActionsObject<State>>(obj: Options2<State, Actions>) => void
->{    state: 100,    actions: {        foo: s => s // Should be typed number => number    },    view: (s, a) => undefined as any,} : { state: number; actions: { foo: (s: number) => number; }; view: (s: number, a: ActionsObject<number>) => any; }
+>{    state: 100,    actions: {        foo: s => s // Should be typed number => number    },    view: (s, a) => undefined as any,} : { state: number; actions: { foo: (s: number) => number; }; view: (s: number, a: { foo: (s: number) => number; }) => any; }
 
     state: 100,
 >state : number
@@ -113,10 +113,10 @@ app2({
 
     },
     view: (s, a) => undefined as any,
->view : (s: number, a: ActionsObject<number>) => any
->(s, a) => undefined as any : (s: number, a: ActionsObject<number>) => any
+>view : (s: number, a: { foo: (s: number) => number; }) => any
+>(s, a) => undefined as any : (s: number, a: { foo: (s: number) => number; }) => any
 >s : number
->a : ActionsObject<number>
+>a : { foo: (s: number) => number; }
 >undefined as any : any
 >undefined : undefined
 
@@ -134,7 +134,7 @@ declare function app3<State, Actions extends ActionsArray<State>>(obj: Options<S
 app3({
 >app3({    state: 100,    actions: [        s => s // Should be typed number => number    ],    view: (s, a) => undefined as any,}) : void
 >app3 : <State, Actions extends ActionsArray<State>>(obj: Options<State, Actions>) => void
->{    state: 100,    actions: [        s => s // Should be typed number => number    ],    view: (s, a) => undefined as any,} : { state: number; actions: ((s: number) => number)[]; view: (s: number, a: ActionsArray<number>) => any; }
+>{    state: 100,    actions: [        s => s // Should be typed number => number    ],    view: (s, a) => undefined as any,} : { state: number; actions: ((s: number) => number)[]; view: (s: number, a: ((s: number) => number)[]) => any; }
 
     state: 100,
 >state : number
@@ -151,10 +151,10 @@ app3({
 
     ],
     view: (s, a) => undefined as any,
->view : (s: number, a: ActionsArray<number>) => any
->(s, a) => undefined as any : (s: number, a: ActionsArray<number>) => any
+>view : (s: number, a: ((s: number) => number)[]) => any
+>(s, a) => undefined as any : (s: number, a: ((s: number) => number)[]) => any
 >s : number
->a : ActionsArray<number>
+>a : ((s: number) => number)[]
 >undefined as any : any
 >undefined : undefined