diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index e59641bed412e..944b975b2b0c5 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -4714,6 +4714,10 @@ namespace ts {
             // function/class/{} assignments are fresh declarations, not property assignments, so only add prototype assignments
             const specialDeclaration = getAssignedJavascriptInitializer(symbol.valueDeclaration);
             if (specialDeclaration) {
+                const tag = getJSDocTypeTag(specialDeclaration);
+                if (tag && tag.typeExpression) {
+                    return getTypeFromTypeNode(tag.typeExpression);
+                }
                 return getWidenedLiteralType(checkExpressionCached(specialDeclaration));
             }
             const types: Type[] = [];
@@ -5081,7 +5085,7 @@ namespace ts {
         }
 
         function getJSInitializerType(decl: Node, symbol: Symbol, init: Expression | undefined): Type | undefined {
-            if (init && isInJavaScriptFile(init) && isObjectLiteralExpression(init)) {
+            if (init && isInJavaScriptFile(init) && isObjectLiteralExpression(init) && init.properties.length === 0) {
                 const exports = createSymbolTable();
                 while (isBinaryExpression(decl) || isPropertyAccessExpression(decl)) {
                     const s = getSymbolOfNode(decl);
@@ -15786,22 +15790,22 @@ namespace ts {
         }
 
         // In an assignment expression, the right operand is contextually typed by the type of the left operand.
-        // Don't do this for special property assignments to avoid circularity.
+        // Don't do this for special property assignments unless there is a type tag on the assignment, to avoid circularity from checking the right operand.
         function isContextSensitiveAssignment(binaryExpression: BinaryExpression): boolean {
             const kind = getSpecialPropertyAssignmentKind(binaryExpression);
             switch (kind) {
                 case SpecialPropertyAssignmentKind.None:
                     return true;
                 case SpecialPropertyAssignmentKind.Property:
-                    // If `binaryExpression.left` was assigned a symbol, then this is a new declaration; otherwise it is an assignment to an existing declaration.
-                    // See `bindStaticPropertyAssignment` in `binder.ts`.
-                    return !binaryExpression.left.symbol;
                 case SpecialPropertyAssignmentKind.ExportsProperty:
-                case SpecialPropertyAssignmentKind.ModuleExports:
+                case SpecialPropertyAssignmentKind.Prototype:
                 case SpecialPropertyAssignmentKind.PrototypeProperty:
+                    // If `binaryExpression.left` was assigned a symbol, then this is a new declaration; otherwise it is an assignment to an existing declaration.
+                    // See `bindStaticPropertyAssignment` in `binder.ts`.
+                    return !binaryExpression.left.symbol || binaryExpression.left.symbol.valueDeclaration && !!getJSDocTypeTag(binaryExpression.left.symbol.valueDeclaration);
                 case SpecialPropertyAssignmentKind.ThisProperty:
-                case SpecialPropertyAssignmentKind.Prototype:
-                    return false;
+                case SpecialPropertyAssignmentKind.ModuleExports:
+                    return !binaryExpression.symbol || binaryExpression.symbol.valueDeclaration && !!getJSDocTypeTag(binaryExpression.symbol.valueDeclaration);
                 default:
                     return Debug.assertNever(kind);
             }
diff --git a/tests/baselines/reference/chainedPrototypeAssignment.types b/tests/baselines/reference/chainedPrototypeAssignment.types
index f0d9cc972ef0f..a893ae63022c6 100644
--- a/tests/baselines/reference/chainedPrototypeAssignment.types
+++ b/tests/baselines/reference/chainedPrototypeAssignment.types
@@ -86,9 +86,9 @@ A.prototype = B.prototype = {
 >A : typeof A
 >prototype : { [x: string]: any; m(n: number): number; }
 >B.prototype = {    /** @param {number} n */    m(n) {        return n + 1    }} : { [x: string]: any; m(n: number): number; }
->B.prototype : { [x: string]: any; }
+>B.prototype : { [x: string]: any; m(n: number): number; }
 >B : typeof B
->prototype : { [x: string]: any; }
+>prototype : { [x: string]: any; m(n: number): number; }
 >{    /** @param {number} n */    m(n) {        return n + 1    }} : { [x: string]: any; m(n: number): number; }
 
     /** @param {number} n */
diff --git a/tests/baselines/reference/conflictingCommonJSES2015Exports.types b/tests/baselines/reference/conflictingCommonJSES2015Exports.types
index a9dc1ce80bd7c..a6afee35f2c09 100644
--- a/tests/baselines/reference/conflictingCommonJSES2015Exports.types
+++ b/tests/baselines/reference/conflictingCommonJSES2015Exports.types
@@ -7,11 +7,11 @@ export function abc(a, b, c) { return 5; }
 >5 : 5
 
 module.exports = { abc };
->module.exports = { abc } : { [x: string]: any; abc: (a: any, b: any, c: any) => number; }
+>module.exports = { abc } : { abc: (a: any, b: any, c: any) => number; }
 >module.exports : any
 >module : any
 >exports : any
->{ abc } : { [x: string]: any; abc: (a: any, b: any, c: any) => number; }
+>{ abc } : { abc: (a: any, b: any, c: any) => number; }
 >abc : (a: any, b: any, c: any) => number
 
 === tests/cases/conformance/salsa/use.js ===
diff --git a/tests/baselines/reference/contextualTypedSpecialAssignment.errors.txt b/tests/baselines/reference/contextualTypedSpecialAssignment.errors.txt
new file mode 100644
index 0000000000000..c5851c4614711
--- /dev/null
+++ b/tests/baselines/reference/contextualTypedSpecialAssignment.errors.txt
@@ -0,0 +1,89 @@
+tests/cases/conformance/salsa/mod.js(5,7): error TS7006: Parameter 'n' implicitly has an 'any' type.
+tests/cases/conformance/salsa/test.js(52,7): error TS7006: Parameter 'n' implicitly has an 'any' type.
+
+
+==== tests/cases/conformance/salsa/test.js (1 errors) ====
+    /** @typedef {{
+        status: 'done'
+        m(n: number): void
+    }} DoneStatus */
+    
+    // property assignment
+    var ns = {}
+    /** @type {DoneStatus} */
+    ns.x = {
+        status: 'done',
+        m(n) { }
+    }
+    
+    ns.x = {
+        status: 'done',
+        m(n) { }
+    }
+    ns.x
+    
+    
+    // this-property assignment
+    class Thing {
+        constructor() {
+            /** @type {DoneStatus} */
+            this.s = {
+                status: 'done',
+                m(n) { }
+            }
+        }
+    
+        fail() {
+            this.s = {
+                status: 'done',
+                m(n) { }
+            }
+        }
+    }
+    
+    // exports-property assignment
+    
+    /** @type {DoneStatus} */
+    exports.x = {
+        status: "done",
+        m(n) { }
+    }
+    exports.x
+    
+    /** @type {DoneStatus} contextual typing is allowed, but module.exports.y: any.
+    Guess it doesn't check the type tag? */
+    module.exports.y = {
+        status: "done",
+        m(n) { }
+          ~
+!!! error TS7006: Parameter 'n' implicitly has an 'any' type.
+    }
+    module.exports.y
+    
+    // prototype-property assignment
+    /** @type {DoneStatus} */
+    Thing.prototype.x = {
+        status: 'done',
+        m(n) { }
+    }
+    Thing.prototype.x
+    
+    // prototype assignment
+    function F() {
+    }
+    /** @type {DoneStatus} */
+    F.prototype = {
+        status: "done",
+        m(n) { }
+    }
+    
+==== tests/cases/conformance/salsa/mod.js (1 errors) ====
+    // module.exports assignment
+    /** @type {{ status: 'done', m(n: number): void }} */
+    module.exports = {
+        status: "done",
+        m(n) { }
+          ~
+!!! error TS7006: Parameter 'n' implicitly has an 'any' type.
+    }
+    
\ No newline at end of file
diff --git a/tests/baselines/reference/contextualTypedSpecialAssignment.symbols b/tests/baselines/reference/contextualTypedSpecialAssignment.symbols
new file mode 100644
index 0000000000000..2a8b1650ae7bc
--- /dev/null
+++ b/tests/baselines/reference/contextualTypedSpecialAssignment.symbols
@@ -0,0 +1,173 @@
+=== tests/cases/conformance/salsa/test.js ===
+/** @typedef {{
+    status: 'done'
+    m(n: number): void
+}} DoneStatus */
+
+// property assignment
+var ns = {}
+>ns : Symbol(ns, Decl(test.js, 6, 3))
+
+/** @type {DoneStatus} */
+ns.x = {
+>ns.x : Symbol(ns.x, Decl(test.js, 6, 11), Decl(test.js, 11, 1))
+>ns : Symbol(ns, Decl(test.js, 6, 3))
+>x : Symbol(ns.x, Decl(test.js, 6, 11), Decl(test.js, 11, 1))
+
+    status: 'done',
+>status : Symbol(status, Decl(test.js, 8, 8))
+
+    m(n) { }
+>m : Symbol(m, Decl(test.js, 9, 19))
+>n : Symbol(n, Decl(test.js, 10, 6))
+}
+
+ns.x = {
+>ns.x : Symbol(ns.x, Decl(test.js, 6, 11), Decl(test.js, 11, 1))
+>ns : Symbol(ns, Decl(test.js, 6, 3))
+>x : Symbol(ns.x, Decl(test.js, 6, 11), Decl(test.js, 11, 1))
+
+    status: 'done',
+>status : Symbol(status, Decl(test.js, 13, 8))
+
+    m(n) { }
+>m : Symbol(m, Decl(test.js, 14, 19))
+>n : Symbol(n, Decl(test.js, 15, 6))
+}
+ns.x
+>ns.x : Symbol(ns.x, Decl(test.js, 6, 11), Decl(test.js, 11, 1))
+>ns : Symbol(ns, Decl(test.js, 6, 3))
+>x : Symbol(ns.x, Decl(test.js, 6, 11), Decl(test.js, 11, 1))
+
+
+// this-property assignment
+class Thing {
+>Thing : Symbol(Thing, Decl(test.js, 17, 4))
+
+    constructor() {
+        /** @type {DoneStatus} */
+        this.s = {
+>this.s : Symbol(Thing.s, Decl(test.js, 22, 19), Decl(test.js, 30, 12))
+>this : Symbol(Thing, Decl(test.js, 17, 4))
+>s : Symbol(Thing.s, Decl(test.js, 22, 19), Decl(test.js, 30, 12))
+
+            status: 'done',
+>status : Symbol(status, Decl(test.js, 24, 18))
+
+            m(n) { }
+>m : Symbol(m, Decl(test.js, 25, 27))
+>n : Symbol(n, Decl(test.js, 26, 14))
+        }
+    }
+
+    fail() {
+>fail : Symbol(Thing.fail, Decl(test.js, 28, 5))
+
+        this.s = {
+>this.s : Symbol(Thing.s, Decl(test.js, 22, 19), Decl(test.js, 30, 12))
+>this : Symbol(Thing, Decl(test.js, 17, 4))
+>s : Symbol(Thing.s, Decl(test.js, 22, 19), Decl(test.js, 30, 12))
+
+            status: 'done',
+>status : Symbol(status, Decl(test.js, 31, 18))
+
+            m(n) { }
+>m : Symbol(m, Decl(test.js, 32, 27))
+>n : Symbol(n, Decl(test.js, 33, 14))
+        }
+    }
+}
+
+// exports-property assignment
+
+/** @type {DoneStatus} */
+exports.x = {
+>exports.x : Symbol(x, Decl(test.js, 36, 1))
+>exports : Symbol(x, Decl(test.js, 36, 1))
+>x : Symbol(x, Decl(test.js, 36, 1))
+
+    status: "done",
+>status : Symbol(status, Decl(test.js, 41, 13))
+
+    m(n) { }
+>m : Symbol(m, Decl(test.js, 42, 19))
+>n : Symbol(n, Decl(test.js, 43, 6))
+}
+exports.x
+>exports.x : Symbol(x, Decl(test.js, 36, 1))
+>exports : Symbol("tests/cases/conformance/salsa/test", Decl(test.js, 0, 0))
+>x : Symbol(x, Decl(test.js, 36, 1))
+
+/** @type {DoneStatus} contextual typing is allowed, but module.exports.y: any.
+Guess it doesn't check the type tag? */
+module.exports.y = {
+>module.exports : Symbol(y, Decl(test.js, 45, 9))
+>module : Symbol(module)
+>y : Symbol(y, Decl(test.js, 45, 9))
+
+    status: "done",
+>status : Symbol(status, Decl(test.js, 49, 20))
+
+    m(n) { }
+>m : Symbol(m, Decl(test.js, 50, 19))
+>n : Symbol(n, Decl(test.js, 51, 6))
+}
+module.exports.y
+>module : Symbol(module)
+
+// prototype-property assignment
+/** @type {DoneStatus} */
+Thing.prototype.x = {
+>Thing.prototype.x : Symbol(Thing.x, Decl(test.js, 53, 16))
+>Thing.prototype : Symbol(Thing.x, Decl(test.js, 53, 16))
+>Thing : Symbol(Thing, Decl(test.js, 17, 4))
+>prototype : Symbol(Thing.prototype)
+>x : Symbol(Thing.x, Decl(test.js, 53, 16))
+
+    status: 'done',
+>status : Symbol(status, Decl(test.js, 57, 21))
+
+    m(n) { }
+>m : Symbol(m, Decl(test.js, 58, 19))
+>n : Symbol(n, Decl(test.js, 59, 6))
+}
+Thing.prototype.x
+>Thing.prototype.x : Symbol(Thing.x, Decl(test.js, 53, 16))
+>Thing.prototype : Symbol(Thing.prototype)
+>Thing : Symbol(Thing, Decl(test.js, 17, 4))
+>prototype : Symbol(Thing.prototype)
+>x : Symbol(Thing.x, Decl(test.js, 53, 16))
+
+// prototype assignment
+function F() {
+>F : Symbol(F, Decl(test.js, 61, 17), Decl(test.js, 65, 1))
+}
+/** @type {DoneStatus} */
+F.prototype = {
+>F.prototype : Symbol(F.prototype, Decl(test.js, 65, 1))
+>F : Symbol(F, Decl(test.js, 61, 17), Decl(test.js, 65, 1))
+>prototype : Symbol(F.prototype, Decl(test.js, 65, 1))
+
+    status: "done",
+>status : Symbol(status, Decl(test.js, 67, 15))
+
+    m(n) { }
+>m : Symbol(m, Decl(test.js, 68, 19))
+>n : Symbol(n, Decl(test.js, 69, 6))
+}
+
+=== tests/cases/conformance/salsa/mod.js ===
+// module.exports assignment
+/** @type {{ status: 'done', m(n: number): void }} */
+module.exports = {
+>module : Symbol(export=, Decl(mod.js, 0, 0))
+>exports : Symbol(export=, Decl(mod.js, 0, 0))
+
+    status: "done",
+>status : Symbol(status, Decl(mod.js, 2, 18))
+
+    m(n) { }
+>m : Symbol(m, Decl(mod.js, 3, 19))
+>n : Symbol(n, Decl(mod.js, 4, 6))
+}
+
diff --git a/tests/baselines/reference/contextualTypedSpecialAssignment.types b/tests/baselines/reference/contextualTypedSpecialAssignment.types
new file mode 100644
index 0000000000000..5bd81e65283e4
--- /dev/null
+++ b/tests/baselines/reference/contextualTypedSpecialAssignment.types
@@ -0,0 +1,208 @@
+=== tests/cases/conformance/salsa/test.js ===
+/** @typedef {{
+    status: 'done'
+    m(n: number): void
+}} DoneStatus */
+
+// property assignment
+var ns = {}
+>ns : { [x: string]: any; x: { status: "done"; m(n: number): void; }; }
+>{} : { [x: string]: any; }
+
+/** @type {DoneStatus} */
+ns.x = {
+>ns.x = {    status: 'done',    m(n) { }} : { status: "done"; m(n: number): void; }
+>ns.x : { status: "done"; m(n: number): void; }
+>ns : { [x: string]: any; x: { status: "done"; m(n: number): void; }; }
+>x : { status: "done"; m(n: number): void; }
+>{    status: 'done',    m(n) { }} : { status: "done"; m(n: number): void; }
+
+    status: 'done',
+>status : "done"
+>'done' : "done"
+
+    m(n) { }
+>m : (n: number) => void
+>n : number
+}
+
+ns.x = {
+>ns.x = {    status: 'done',    m(n) { }} : { status: "done"; m(n: number): void; }
+>ns.x : { status: "done"; m(n: number): void; }
+>ns : { [x: string]: any; x: { status: "done"; m(n: number): void; }; }
+>x : { status: "done"; m(n: number): void; }
+>{    status: 'done',    m(n) { }} : { status: "done"; m(n: number): void; }
+
+    status: 'done',
+>status : "done"
+>'done' : "done"
+
+    m(n) { }
+>m : (n: number) => void
+>n : number
+}
+ns.x
+>ns.x : { status: "done"; m(n: number): void; }
+>ns : { [x: string]: any; x: { status: "done"; m(n: number): void; }; }
+>x : { status: "done"; m(n: number): void; }
+
+
+// this-property assignment
+class Thing {
+>Thing : Thing
+
+    constructor() {
+        /** @type {DoneStatus} */
+        this.s = {
+>this.s = {            status: 'done',            m(n) { }        } : { status: "done"; m(n: number): void; }
+>this.s : { status: "done"; m(n: number): void; }
+>this : this
+>s : { status: "done"; m(n: number): void; }
+>{            status: 'done',            m(n) { }        } : { status: "done"; m(n: number): void; }
+
+            status: 'done',
+>status : "done"
+>'done' : "done"
+
+            m(n) { }
+>m : (n: number) => void
+>n : number
+        }
+    }
+
+    fail() {
+>fail : () => void
+
+        this.s = {
+>this.s = {            status: 'done',            m(n) { }        } : { status: "done"; m(n: number): void; }
+>this.s : { status: "done"; m(n: number): void; }
+>this : this
+>s : { status: "done"; m(n: number): void; }
+>{            status: 'done',            m(n) { }        } : { status: "done"; m(n: number): void; }
+
+            status: 'done',
+>status : "done"
+>'done' : "done"
+
+            m(n) { }
+>m : (n: number) => void
+>n : number
+        }
+    }
+}
+
+// exports-property assignment
+
+/** @type {DoneStatus} */
+exports.x = {
+>exports.x = {    status: "done",    m(n) { }} : { status: "done"; m(n: number): void; }
+>exports.x : { status: "done"; m(n: number): void; }
+>exports : typeof import("tests/cases/conformance/salsa/test")
+>x : { status: "done"; m(n: number): void; }
+>{    status: "done",    m(n) { }} : { status: "done"; m(n: number): void; }
+
+    status: "done",
+>status : "done"
+>"done" : "done"
+
+    m(n) { }
+>m : (n: number) => void
+>n : number
+}
+exports.x
+>exports.x : { status: "done"; m(n: number): void; }
+>exports : typeof import("tests/cases/conformance/salsa/test")
+>x : { status: "done"; m(n: number): void; }
+
+/** @type {DoneStatus} contextual typing is allowed, but module.exports.y: any.
+Guess it doesn't check the type tag? */
+module.exports.y = {
+>module.exports.y = {    status: "done",    m(n) { }} : { status: string; m(n: any): void; }
+>module.exports.y : any
+>module.exports : any
+>module : any
+>exports : any
+>y : any
+>{    status: "done",    m(n) { }} : { status: string; m(n: any): void; }
+
+    status: "done",
+>status : string
+>"done" : "done"
+
+    m(n) { }
+>m : (n: any) => void
+>n : any
+}
+module.exports.y
+>module.exports.y : any
+>module.exports : any
+>module : any
+>exports : any
+>y : any
+
+// prototype-property assignment
+/** @type {DoneStatus} */
+Thing.prototype.x = {
+>Thing.prototype.x = {    status: 'done',    m(n) { }} : { status: "done"; m(n: number): void; }
+>Thing.prototype.x : { status: "done"; m(n: number): void; }
+>Thing.prototype : Thing
+>Thing : typeof Thing
+>prototype : Thing
+>x : { status: "done"; m(n: number): void; }
+>{    status: 'done',    m(n) { }} : { status: "done"; m(n: number): void; }
+
+    status: 'done',
+>status : "done"
+>'done' : "done"
+
+    m(n) { }
+>m : (n: number) => void
+>n : number
+}
+Thing.prototype.x
+>Thing.prototype.x : { status: "done"; m(n: number): void; }
+>Thing.prototype : Thing
+>Thing : typeof Thing
+>prototype : Thing
+>x : { status: "done"; m(n: number): void; }
+
+// prototype assignment
+function F() {
+>F : typeof F
+}
+/** @type {DoneStatus} */
+F.prototype = {
+>F.prototype = {    status: "done",    m(n) { }} : { status: "done"; m(n: number): void; }
+>F.prototype : { status: "done"; m(n: number): void; }
+>F : typeof F
+>prototype : { status: "done"; m(n: number): void; }
+>{    status: "done",    m(n) { }} : { status: "done"; m(n: number): void; }
+
+    status: "done",
+>status : "done"
+>"done" : "done"
+
+    m(n) { }
+>m : (n: number) => void
+>n : number
+}
+
+=== tests/cases/conformance/salsa/mod.js ===
+// module.exports assignment
+/** @type {{ status: 'done', m(n: number): void }} */
+module.exports = {
+>module.exports = {    status: "done",    m(n) { }} : { status: string; m(n: any): void; }
+>module.exports : any
+>module : any
+>exports : any
+>{    status: "done",    m(n) { }} : { status: string; m(n: any): void; }
+
+    status: "done",
+>status : string
+>"done" : "done"
+
+    m(n) { }
+>m : (n: any) => void
+>n : any
+}
+
diff --git a/tests/baselines/reference/moduleExportAlias.types b/tests/baselines/reference/moduleExportAlias.types
index 924f02d7fa866..707dc90a1f5c7 100644
--- a/tests/baselines/reference/moduleExportAlias.types
+++ b/tests/baselines/reference/moduleExportAlias.types
@@ -223,19 +223,19 @@ multipleDeclarationAlias5.func9 = function () { };
 >function () { } : () => void
 
 var multipleDeclarationAlias6 = exports = module.exports = {};
->multipleDeclarationAlias6 : { [x: string]: any; }
->exports = module.exports = {} : { [x: string]: any; }
+>multipleDeclarationAlias6 : {}
+>exports = module.exports = {} : {}
 >exports : typeof import("tests/cases/conformance/salsa/b")
->module.exports = {} : { [x: string]: any; }
+>module.exports = {} : {}
 >module.exports : any
 >module : any
 >exports : any
->{} : { [x: string]: any; }
+>{} : {}
 
 multipleDeclarationAlias6.func10 = function () { };
 >multipleDeclarationAlias6.func10 = function () { } : () => void
 >multipleDeclarationAlias6.func10 : any
->multipleDeclarationAlias6 : { [x: string]: any; }
+>multipleDeclarationAlias6 : {}
 >func10 : any
 >function () { } : () => void
 
@@ -294,13 +294,13 @@ module.exports.func12 = function () { };
 >function () { } : () => void
 
 exports = module.exports = {};
->exports = module.exports = {} : { [x: string]: any; }
+>exports = module.exports = {} : {}
 >exports : typeof import("tests/cases/conformance/salsa/b")
->module.exports = {} : { [x: string]: any; }
+>module.exports = {} : {}
 >module.exports : any
 >module : any
 >exports : any
->{} : { [x: string]: any; }
+>{} : {}
 
 exports.func13 = function () { };
 >exports.func13 = function () { } : () => void
@@ -319,13 +319,13 @@ module.exports.func14 = function () { };
 >function () { } : () => void
 
 exports = module.exports = {};
->exports = module.exports = {} : { [x: string]: any; }
+>exports = module.exports = {} : {}
 >exports : typeof import("tests/cases/conformance/salsa/b")
->module.exports = {} : { [x: string]: any; }
+>module.exports = {} : {}
 >module.exports : any
 >module : any
 >exports : any
->{} : { [x: string]: any; }
+>{} : {}
 
 exports.func15 = function () { };
 >exports.func15 = function () { } : () => void
@@ -369,11 +369,11 @@ module.exports.func18 = function () { };
 >function () { } : () => void
 
 module.exports = {};
->module.exports = {} : { [x: string]: any; }
+>module.exports = {} : {}
 >module.exports : any
 >module : any
 >exports : any
->{} : { [x: string]: any; }
+>{} : {}
 
 exports.func19 = function () { };
 >exports.func19 = function () { } : () => void
diff --git a/tests/baselines/reference/typeFromPropertyAssignment11.types b/tests/baselines/reference/typeFromPropertyAssignment11.types
index 87a709d7cf3a4..8c90e824f23c5 100644
--- a/tests/baselines/reference/typeFromPropertyAssignment11.types
+++ b/tests/baselines/reference/typeFromPropertyAssignment11.types
@@ -5,9 +5,9 @@ var Inner = function() {}
 
 Inner.prototype = {
 >Inner.prototype = {    m() { },    i: 1} : { [x: string]: any; m(): void; i: number; }
->Inner.prototype : { [x: string]: any; }
+>Inner.prototype : { [x: string]: any; m(): void; i: number; }
 >Inner : typeof Inner
->prototype : { [x: string]: any; }
+>prototype : { [x: string]: any; m(): void; i: number; }
 >{    m() { },    i: 1} : { [x: string]: any; m(): void; i: number; }
 
     m() { },
@@ -21,18 +21,18 @@ Inner.prototype = {
 Inner.prototype.j = 2
 >Inner.prototype.j = 2 : 2
 >Inner.prototype.j : any
->Inner.prototype : { [x: string]: any; }
+>Inner.prototype : { [x: string]: any; m(): void; i: number; }
 >Inner : typeof Inner
->prototype : { [x: string]: any; }
+>prototype : { [x: string]: any; m(): void; i: number; }
 >j : any
 >2 : 2
 
 /** @type {string} */
 Inner.prototype.k;
 >Inner.prototype.k : any
->Inner.prototype : { [x: string]: any; }
+>Inner.prototype : { [x: string]: any; m(): void; i: number; }
 >Inner : typeof Inner
->prototype : { [x: string]: any; }
+>prototype : { [x: string]: any; m(): void; i: number; }
 >k : any
 
 var inner = new Inner()
diff --git a/tests/baselines/reference/typeFromPropertyAssignment13.types b/tests/baselines/reference/typeFromPropertyAssignment13.types
index 5b97d2986f57c..f85325a60a22c 100644
--- a/tests/baselines/reference/typeFromPropertyAssignment13.types
+++ b/tests/baselines/reference/typeFromPropertyAssignment13.types
@@ -12,11 +12,11 @@ Outer.Inner = function() {}
 
 Outer.Inner.prototype = {
 >Outer.Inner.prototype = {    m() { },    i: 1} : { [x: string]: any; m(): void; i: number; }
->Outer.Inner.prototype : { [x: string]: any; }
+>Outer.Inner.prototype : { [x: string]: any; m(): void; i: number; }
 >Outer.Inner : typeof Inner
 >Outer : typeof Outer
 >Inner : typeof Inner
->prototype : { [x: string]: any; }
+>prototype : { [x: string]: any; m(): void; i: number; }
 >{    m() { },    i: 1} : { [x: string]: any; m(): void; i: number; }
 
     m() { },
@@ -30,22 +30,22 @@ Outer.Inner.prototype = {
 Outer.Inner.prototype.j = 2
 >Outer.Inner.prototype.j = 2 : 2
 >Outer.Inner.prototype.j : any
->Outer.Inner.prototype : { [x: string]: any; }
+>Outer.Inner.prototype : { [x: string]: any; m(): void; i: number; }
 >Outer.Inner : typeof Inner
 >Outer : typeof Outer
 >Inner : typeof Inner
->prototype : { [x: string]: any; }
+>prototype : { [x: string]: any; m(): void; i: number; }
 >j : any
 >2 : 2
 
 /** @type {string} */
 Outer.Inner.prototype.k;
 >Outer.Inner.prototype.k : any
->Outer.Inner.prototype : { [x: string]: any; }
+>Outer.Inner.prototype : { [x: string]: any; m(): void; i: number; }
 >Outer.Inner : typeof Inner
 >Outer : typeof Outer
 >Inner : typeof Inner
->prototype : { [x: string]: any; }
+>prototype : { [x: string]: any; m(): void; i: number; }
 >k : any
 
 var inner = new Outer.Inner()
diff --git a/tests/baselines/reference/typeFromPropertyAssignment14.types b/tests/baselines/reference/typeFromPropertyAssignment14.types
index 60d63c489d6b3..a20a5a15fc3c6 100644
--- a/tests/baselines/reference/typeFromPropertyAssignment14.types
+++ b/tests/baselines/reference/typeFromPropertyAssignment14.types
@@ -5,19 +5,19 @@ var Outer = {};
 
 === tests/cases/conformance/salsa/work.js ===
 Outer.Inner = function () {}
->Outer.Inner = function () {} : { (): void; prototype: { [x: string]: any; }; }
->Outer.Inner : { (): void; prototype: { [x: string]: any; }; }
+>Outer.Inner = function () {} : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
+>Outer.Inner : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
 >Outer : typeof Outer
->Inner : { (): void; prototype: { [x: string]: any; }; }
->function () {} : { (): void; prototype: { [x: string]: any; }; }
+>Inner : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
+>function () {} : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
 
 Outer.Inner.prototype = {
 >Outer.Inner.prototype = {    x: 1,    m() { }} : { [x: string]: any; x: number; m(): void; }
->Outer.Inner.prototype : { [x: string]: any; }
->Outer.Inner : { (): void; prototype: { [x: string]: any; }; }
+>Outer.Inner.prototype : { [x: string]: any; x: number; m(): void; }
+>Outer.Inner : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
 >Outer : typeof Outer
->Inner : { (): void; prototype: { [x: string]: any; }; }
->prototype : { [x: string]: any; }
+>Inner : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
+>prototype : { [x: string]: any; x: number; m(): void; }
 >{    x: 1,    m() { }} : { [x: string]: any; x: number; m(): void; }
 
     x: 1,
@@ -47,9 +47,9 @@ inner.m()
 var inno = new Outer.Inner()
 >inno : { [x: string]: any; x: number; m(): void; }
 >new Outer.Inner() : { [x: string]: any; x: number; m(): void; }
->Outer.Inner : { (): void; prototype: { [x: string]: any; }; }
+>Outer.Inner : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
 >Outer : typeof Outer
->Inner : { (): void; prototype: { [x: string]: any; }; }
+>Inner : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
 
 inno.x
 >inno.x : number
diff --git a/tests/baselines/reference/typeFromPropertyAssignment16.types b/tests/baselines/reference/typeFromPropertyAssignment16.types
index d67d6ccca3763..ce0ae3ae16e23 100644
--- a/tests/baselines/reference/typeFromPropertyAssignment16.types
+++ b/tests/baselines/reference/typeFromPropertyAssignment16.types
@@ -4,19 +4,19 @@ var Outer = {};
 >{} : { [x: string]: any; }
 
 Outer.Inner = function () {}
->Outer.Inner = function () {} : { (): void; prototype: { [x: string]: any; }; }
->Outer.Inner : { (): void; prototype: { [x: string]: any; }; }
+>Outer.Inner = function () {} : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
+>Outer.Inner : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
 >Outer : typeof Outer
->Inner : { (): void; prototype: { [x: string]: any; }; }
->function () {} : { (): void; prototype: { [x: string]: any; }; }
+>Inner : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
+>function () {} : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
 
 Outer.Inner.prototype = {
 >Outer.Inner.prototype = {    x: 1,    m() { }} : { [x: string]: any; x: number; m(): void; }
->Outer.Inner.prototype : { [x: string]: any; }
->Outer.Inner : { (): void; prototype: { [x: string]: any; }; }
+>Outer.Inner.prototype : { [x: string]: any; x: number; m(): void; }
+>Outer.Inner : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
 >Outer : typeof Outer
->Inner : { (): void; prototype: { [x: string]: any; }; }
->prototype : { [x: string]: any; }
+>Inner : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
+>prototype : { [x: string]: any; x: number; m(): void; }
 >{    x: 1,    m() { }} : { [x: string]: any; x: number; m(): void; }
 
     x: 1,
@@ -45,9 +45,9 @@ inner.m()
 var inno = new Outer.Inner()
 >inno : { [x: string]: any; x: number; m(): void; }
 >new Outer.Inner() : { [x: string]: any; x: number; m(): void; }
->Outer.Inner : { (): void; prototype: { [x: string]: any; }; }
+>Outer.Inner : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
 >Outer : typeof Outer
->Inner : { (): void; prototype: { [x: string]: any; }; }
+>Inner : { (): void; prototype: { [x: string]: any; x: number; m(): void; }; }
 
 inno.x
 >inno.x : number
diff --git a/tests/baselines/reference/typeFromPropertyAssignment27.types b/tests/baselines/reference/typeFromPropertyAssignment27.types
index 222bd04e74d14..dcaefe7a95575 100644
--- a/tests/baselines/reference/typeFromPropertyAssignment27.types
+++ b/tests/baselines/reference/typeFromPropertyAssignment27.types
@@ -10,9 +10,9 @@ function C() { this.p = 1; }
 
 C.prototype = { q: 2 };
 >C.prototype = { q: 2 } : { [x: string]: any; q: number; }
->C.prototype : { [x: string]: any; }
+>C.prototype : { [x: string]: any; q: number; }
 >C : typeof C
->prototype : { [x: string]: any; }
+>prototype : { [x: string]: any; q: number; }
 >{ q: 2 } : { [x: string]: any; q: number; }
 >q : number
 >2 : 2
diff --git a/tests/cases/conformance/salsa/contextualTypedSpecialAssignment.ts b/tests/cases/conformance/salsa/contextualTypedSpecialAssignment.ts
new file mode 100644
index 0000000000000..e4a2b56970c1b
--- /dev/null
+++ b/tests/cases/conformance/salsa/contextualTypedSpecialAssignment.ts
@@ -0,0 +1,84 @@
+// @checkJs: true
+// @allowJs: true
+// @noEmit: true
+// @Filename: test.js
+// @strict: true
+/** @typedef {{
+    status: 'done'
+    m(n: number): void
+}} DoneStatus */
+
+// property assignment
+var ns = {}
+/** @type {DoneStatus} */
+ns.x = {
+    status: 'done',
+    m(n) { }
+}
+
+ns.x = {
+    status: 'done',
+    m(n) { }
+}
+ns.x
+
+
+// this-property assignment
+class Thing {
+    constructor() {
+        /** @type {DoneStatus} */
+        this.s = {
+            status: 'done',
+            m(n) { }
+        }
+    }
+
+    fail() {
+        this.s = {
+            status: 'done',
+            m(n) { }
+        }
+    }
+}
+
+// exports-property assignment
+
+/** @type {DoneStatus} */
+exports.x = {
+    status: "done",
+    m(n) { }
+}
+exports.x
+
+/** @type {DoneStatus} contextual typing is allowed, but module.exports.y: any.
+Guess it doesn't check the type tag? */
+module.exports.y = {
+    status: "done",
+    m(n) { }
+}
+module.exports.y
+
+// prototype-property assignment
+/** @type {DoneStatus} */
+Thing.prototype.x = {
+    status: 'done',
+    m(n) { }
+}
+Thing.prototype.x
+
+// prototype assignment
+function F() {
+}
+/** @type {DoneStatus} */
+F.prototype = {
+    status: "done",
+    m(n) { }
+}
+
+// @Filename: mod.js
+// module.exports assignment
+/** @type {{ status: 'done', m(n: number): void }} */
+module.exports = {
+    status: "done",
+    m(n) { }
+}