diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 59f2d40799c..62a15349dec 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -535,9 +535,11 @@ import {
     isJSDocNode,
     isJSDocNonNullableType,
     isJSDocNullableType,
+    isJSDocOptionalParameter,
     isJSDocOptionalType,
     isJSDocParameterTag,
     isJSDocPropertyLikeTag,
+    isJSDocPropertyTag,
     isJSDocReturnTag,
     isJSDocSignature,
     isJSDocTemplateTag,
@@ -599,6 +601,7 @@ import {
     isOmittedExpression,
     isOptionalChain,
     isOptionalChainRoot,
+    isOptionalDeclaration,
     isOptionalJSDocPropertyLikeTag,
     isOptionalTypeNode,
     isOutermostOptionalChain,
@@ -10164,11 +10167,8 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             return getTypeForBindingElement(declaration as BindingElement);
         }
 
-        const isProperty = isPropertyDeclaration(declaration) && !hasAccessorModifier(declaration) || isPropertySignature(declaration);
-        const isOptional = includeOptionality && (
-            isProperty && !!declaration.questionToken ||
-            isParameter(declaration) && (!!declaration.questionToken || isJSDocOptionalParameter(declaration)) ||
-            isOptionalJSDocPropertyLikeTag(declaration));
+        const isProperty = (isPropertyDeclaration(declaration) && !hasAccessorModifier(declaration)) || isPropertySignature(declaration) || isJSDocPropertyTag(declaration);
+        const isOptional = includeOptionality && isOptionalDeclaration(declaration);
 
         // Use type from type annotation if one is present
         const declaredType = tryGetTypeFromEffectiveTypeNode(declaration);
@@ -13991,14 +13991,6 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         return result;
     }
 
-    function isJSDocOptionalParameter(node: ParameterDeclaration) {
-        return isInJSFile(node) && (
-            // node.type should only be a JSDocOptionalType when node is a parameter of a JSDocFunctionType
-            node.type && node.type.kind === SyntaxKind.JSDocOptionalType
-            || getJSDocParameterTags(node).some(({ isBracketed, typeExpression }) =>
-                isBracketed || !!typeExpression && typeExpression.type.kind === SyntaxKind.JSDocOptionalType));
-    }
-
     function tryFindAmbientModule(moduleName: string, withAugmentations: boolean) {
         if (isExternalModuleNameRelative(moduleName)) {
             return undefined;
diff --git a/src/compiler/utilities.ts b/src/compiler/utilities.ts
index d2bb79697a4..252ebe202f8 100644
--- a/src/compiler/utilities.ts
+++ b/src/compiler/utilities.ts
@@ -414,6 +414,7 @@ import {
     PropertyDeclaration,
     PropertyName,
     PropertyNameLiteral,
+    PropertySignature,
     PseudoBigInt,
     QualifiedName,
     ReadonlyCollection,
@@ -9139,3 +9140,26 @@ export function canUsePropertyAccess(name: string, languageVersion: ScriptTarget
 export function hasTabstop(node: Node): boolean {
     return getSnippetElement(node)?.kind === SnippetKind.TabStop;
 }
+
+export function isJSDocOptionalParameter(node: ParameterDeclaration) {
+    return isInJSFile(node) && (
+        // node.type should only be a JSDocOptionalType when node is a parameter of a JSDocFunctionType
+        node.type && node.type.kind === SyntaxKind.JSDocOptionalType
+        || getJSDocParameterTags(node).some(({ isBracketed, typeExpression }) =>
+            isBracketed || !!typeExpression && typeExpression.type.kind === SyntaxKind.JSDocOptionalType));
+}
+
+export function isOptionalDeclaration(declaration: Declaration): boolean {
+    switch (declaration.kind) {
+        case SyntaxKind.PropertyDeclaration:
+        case SyntaxKind.PropertySignature:
+            return !!(declaration as PropertyDeclaration | PropertySignature).questionToken;
+        case SyntaxKind.Parameter:
+            return !!(declaration as ParameterDeclaration).questionToken || isJSDocOptionalParameter(declaration as ParameterDeclaration);
+        case SyntaxKind.JSDocPropertyTag:
+        case SyntaxKind.JSDocParameterTag:
+            return isOptionalJSDocPropertyLikeTag(declaration);
+        default:
+            return false;
+    }
+}
diff --git a/tests/baselines/reference/api/tsserverlibrary.d.ts b/tests/baselines/reference/api/tsserverlibrary.d.ts
index e7d7ff77215..be4bf4cb7a4 100644
--- a/tests/baselines/reference/api/tsserverlibrary.d.ts
+++ b/tests/baselines/reference/api/tsserverlibrary.d.ts
@@ -8766,6 +8766,8 @@ declare namespace ts {
         parent: ConstructorDeclaration;
         name: Identifier;
     };
+    function isJSDocOptionalParameter(node: ParameterDeclaration): boolean;
+    function isOptionalDeclaration(declaration: Declaration): boolean;
     function createUnparsedSourceFile(text: string): UnparsedSource;
     function createUnparsedSourceFile(inputFile: InputFiles, type: "js" | "dts", stripInternal?: boolean): UnparsedSource;
     function createUnparsedSourceFile(text: string, mapPath: string | undefined, map: string | undefined): UnparsedSource;
diff --git a/tests/baselines/reference/api/typescript.d.ts b/tests/baselines/reference/api/typescript.d.ts
index 8ce49d6142f..8ddf62571c5 100644
--- a/tests/baselines/reference/api/typescript.d.ts
+++ b/tests/baselines/reference/api/typescript.d.ts
@@ -4832,6 +4832,8 @@ declare namespace ts {
         parent: ConstructorDeclaration;
         name: Identifier;
     };
+    function isJSDocOptionalParameter(node: ParameterDeclaration): boolean;
+    function isOptionalDeclaration(declaration: Declaration): boolean;
     function createUnparsedSourceFile(text: string): UnparsedSource;
     function createUnparsedSourceFile(inputFile: InputFiles, type: "js" | "dts", stripInternal?: boolean): UnparsedSource;
     function createUnparsedSourceFile(text: string, mapPath: string | undefined, map: string | undefined): UnparsedSource;
diff --git a/tests/baselines/reference/strictOptionalProperties3.errors.txt b/tests/baselines/reference/strictOptionalProperties3.errors.txt
new file mode 100644
index 00000000000..1c56589165c
--- /dev/null
+++ b/tests/baselines/reference/strictOptionalProperties3.errors.txt
@@ -0,0 +1,32 @@
+tests/cases/compiler/a.js(7,7): error TS2375: Type '{ value: undefined; }' is not assignable to type 'A' with 'exactOptionalPropertyTypes: true'. Consider adding 'undefined' to the types of the target's properties.
+  Types of property 'value' are incompatible.
+    Type 'undefined' is not assignable to type 'number'.
+tests/cases/compiler/a.js(14,7): error TS2375: Type '{ value: undefined; }' is not assignable to type 'B' with 'exactOptionalPropertyTypes: true'. Consider adding 'undefined' to the types of the target's properties.
+  Types of property 'value' are incompatible.
+    Type 'undefined' is not assignable to type 'number'.
+
+
+==== tests/cases/compiler/a.js (2 errors) ====
+    /**
+     * @typedef {object} A
+     * @property {number} [value]
+     */
+    
+    /** @type {A} */
+    const a = { value: undefined }; // error
+          ~
+!!! error TS2375: Type '{ value: undefined; }' is not assignable to type 'A' with 'exactOptionalPropertyTypes: true'. Consider adding 'undefined' to the types of the target's properties.
+!!! error TS2375:   Types of property 'value' are incompatible.
+!!! error TS2375:     Type 'undefined' is not assignable to type 'number'.
+    
+    /**
+     * @typedef {{ value?: number }} B
+     */
+    
+    /** @type {B} */
+    const b = { value: undefined }; // error
+          ~
+!!! error TS2375: Type '{ value: undefined; }' is not assignable to type 'B' with 'exactOptionalPropertyTypes: true'. Consider adding 'undefined' to the types of the target's properties.
+!!! error TS2375:   Types of property 'value' are incompatible.
+!!! error TS2375:     Type 'undefined' is not assignable to type 'number'.
+    
\ No newline at end of file
diff --git a/tests/baselines/reference/strictOptionalProperties3.symbols b/tests/baselines/reference/strictOptionalProperties3.symbols
new file mode 100644
index 00000000000..db658b8cbcb
--- /dev/null
+++ b/tests/baselines/reference/strictOptionalProperties3.symbols
@@ -0,0 +1,22 @@
+=== tests/cases/compiler/a.js ===
+/**
+ * @typedef {object} A
+ * @property {number} [value]
+ */
+
+/** @type {A} */
+const a = { value: undefined }; // error
+>a : Symbol(a, Decl(a.js, 6, 5))
+>value : Symbol(value, Decl(a.js, 6, 11))
+>undefined : Symbol(undefined)
+
+/**
+ * @typedef {{ value?: number }} B
+ */
+
+/** @type {B} */
+const b = { value: undefined }; // error
+>b : Symbol(b, Decl(a.js, 13, 5))
+>value : Symbol(value, Decl(a.js, 13, 11))
+>undefined : Symbol(undefined)
+
diff --git a/tests/baselines/reference/strictOptionalProperties3.types b/tests/baselines/reference/strictOptionalProperties3.types
new file mode 100644
index 00000000000..5f8c18f5648
--- /dev/null
+++ b/tests/baselines/reference/strictOptionalProperties3.types
@@ -0,0 +1,24 @@
+=== tests/cases/compiler/a.js ===
+/**
+ * @typedef {object} A
+ * @property {number} [value]
+ */
+
+/** @type {A} */
+const a = { value: undefined }; // error
+>a : A
+>{ value: undefined } : { value: undefined; }
+>value : undefined
+>undefined : undefined
+
+/**
+ * @typedef {{ value?: number }} B
+ */
+
+/** @type {B} */
+const b = { value: undefined }; // error
+>b : B
+>{ value: undefined } : { value: undefined; }
+>value : undefined
+>undefined : undefined
+
diff --git a/tests/baselines/reference/strictOptionalProperties4.symbols b/tests/baselines/reference/strictOptionalProperties4.symbols
new file mode 100644
index 00000000000..22c970fc6ac
--- /dev/null
+++ b/tests/baselines/reference/strictOptionalProperties4.symbols
@@ -0,0 +1,22 @@
+=== tests/cases/compiler/a.js ===
+/**
+ * @typedef Foo
+ * @property {number} [foo]
+ */
+
+const x = /** @type {Foo} */ ({});
+>x : Symbol(x, Decl(a.js, 5, 5))
+
+x.foo; // number | undefined
+>x.foo : Symbol(foo, Decl(a.js, 2, 3))
+>x : Symbol(x, Decl(a.js, 5, 5))
+>foo : Symbol(foo, Decl(a.js, 2, 3))
+
+const y = /** @type {Required<Foo>} */ ({});
+>y : Symbol(y, Decl(a.js, 8, 5))
+
+y.foo; // number
+>y.foo : Symbol(foo, Decl(a.js, 2, 3))
+>y : Symbol(y, Decl(a.js, 8, 5))
+>foo : Symbol(foo, Decl(a.js, 2, 3))
+
diff --git a/tests/baselines/reference/strictOptionalProperties4.types b/tests/baselines/reference/strictOptionalProperties4.types
new file mode 100644
index 00000000000..fb7c6ed9186
--- /dev/null
+++ b/tests/baselines/reference/strictOptionalProperties4.types
@@ -0,0 +1,26 @@
+=== tests/cases/compiler/a.js ===
+/**
+ * @typedef Foo
+ * @property {number} [foo]
+ */
+
+const x = /** @type {Foo} */ ({});
+>x : Foo
+>({}) : Foo
+>{} : {}
+
+x.foo; // number | undefined
+>x.foo : number | undefined
+>x : Foo
+>foo : number | undefined
+
+const y = /** @type {Required<Foo>} */ ({});
+>y : Required<Foo>
+>({}) : Required<Foo>
+>{} : {}
+
+y.foo; // number
+>y.foo : number
+>y : Required<Foo>
+>foo : number
+
diff --git a/tests/cases/compiler/strictOptionalProperties3.ts b/tests/cases/compiler/strictOptionalProperties3.ts
new file mode 100644
index 00000000000..c1bff467f19
--- /dev/null
+++ b/tests/cases/compiler/strictOptionalProperties3.ts
@@ -0,0 +1,21 @@
+// @strictNullChecks: true
+// @exactOptionalPropertyTypes: true
+// @allowJs: true
+// @checkJs: true
+// @noEmit: true
+// @filename: a.js
+
+/**
+ * @typedef {object} A
+ * @property {number} [value]
+ */
+
+/** @type {A} */
+const a = { value: undefined }; // error
+
+/**
+ * @typedef {{ value?: number }} B
+ */
+
+/** @type {B} */
+const b = { value: undefined }; // error
diff --git a/tests/cases/compiler/strictOptionalProperties4.ts b/tests/cases/compiler/strictOptionalProperties4.ts
new file mode 100644
index 00000000000..c902cde58b2
--- /dev/null
+++ b/tests/cases/compiler/strictOptionalProperties4.ts
@@ -0,0 +1,17 @@
+// @strictNullChecks: true
+// @exactOptionalPropertyTypes: true
+// @allowJs: true
+// @checkJs: true
+// @noEmit: true
+// @filename: a.js
+
+/**
+ * @typedef Foo
+ * @property {number} [foo]
+ */
+
+const x = /** @type {Foo} */ ({});
+x.foo; // number | undefined
+
+const y = /** @type {Required<Foo>} */ ({});
+y.foo; // number