diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 6ece23f022a..c2603e1f30b 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -23593,7 +23593,20 @@ namespace ts {
                 // If the signature's 'this' type is voidType, then the check is skipped -- anything is compatible.
                 // If the expression is a new expression, then the check is skipped.
                 const thisArgumentNode = getThisArgumentOfCall(node);
-                const thisArgumentType = thisArgumentNode ? checkExpression(thisArgumentNode) : voidType;
+                let thisArgumentType: Type;
+                if (thisArgumentNode) {
+                    thisArgumentType = checkExpression(thisArgumentNode);
+                    if (isOptionalChainRoot(thisArgumentNode.parent)) {
+                        thisArgumentType = getNonNullableType(thisArgumentType);
+                    }
+                    else if (isOptionalChain(thisArgumentNode.parent)) {
+                        thisArgumentType = removeOptionalTypeMarker(thisArgumentType);
+                    }
+                }
+                else {
+                    thisArgumentType = voidType;
+                }
+
                 const errorNode = reportErrors ? (thisArgumentNode || node) : undefined;
                 const headMessage = Diagnostics.The_this_context_of_type_0_is_not_assignable_to_method_s_this_of_type_1;
                 if (!checkTypeRelatedTo(thisArgumentType, thisType, relation, errorNode, headMessage, containingMessageChain, errorOutputContainer)) {
diff --git a/tests/baselines/reference/thisTypeOptionalCall.js b/tests/baselines/reference/thisTypeOptionalCall.js
new file mode 100644
index 00000000000..2a7a24d6eeb
--- /dev/null
+++ b/tests/baselines/reference/thisTypeOptionalCall.js
@@ -0,0 +1,10 @@
+//// [thisTypeOptionalCall.ts]
+function maybeBind<T, A extends any[], R>(obj: T, fn: ((this: T, ...args: A) => R) | undefined): ((...args: A) => R) | undefined {
+    return fn?.bind(obj);
+}
+
+//// [thisTypeOptionalCall.js]
+function maybeBind(obj, fn) {
+    var _a;
+    return (_a = fn) === null || _a === void 0 ? void 0 : _a.bind(obj);
+}
diff --git a/tests/baselines/reference/thisTypeOptionalCall.symbols b/tests/baselines/reference/thisTypeOptionalCall.symbols
new file mode 100644
index 00000000000..d55d8c823c1
--- /dev/null
+++ b/tests/baselines/reference/thisTypeOptionalCall.symbols
@@ -0,0 +1,24 @@
+=== tests/cases/conformance/types/thisType/thisTypeOptionalCall.ts ===
+function maybeBind<T, A extends any[], R>(obj: T, fn: ((this: T, ...args: A) => R) | undefined): ((...args: A) => R) | undefined {
+>maybeBind : Symbol(maybeBind, Decl(thisTypeOptionalCall.ts, 0, 0))
+>T : Symbol(T, Decl(thisTypeOptionalCall.ts, 0, 19))
+>A : Symbol(A, Decl(thisTypeOptionalCall.ts, 0, 21))
+>R : Symbol(R, Decl(thisTypeOptionalCall.ts, 0, 38))
+>obj : Symbol(obj, Decl(thisTypeOptionalCall.ts, 0, 42))
+>T : Symbol(T, Decl(thisTypeOptionalCall.ts, 0, 19))
+>fn : Symbol(fn, Decl(thisTypeOptionalCall.ts, 0, 49))
+>this : Symbol(this, Decl(thisTypeOptionalCall.ts, 0, 56))
+>T : Symbol(T, Decl(thisTypeOptionalCall.ts, 0, 19))
+>args : Symbol(args, Decl(thisTypeOptionalCall.ts, 0, 64))
+>A : Symbol(A, Decl(thisTypeOptionalCall.ts, 0, 21))
+>R : Symbol(R, Decl(thisTypeOptionalCall.ts, 0, 38))
+>args : Symbol(args, Decl(thisTypeOptionalCall.ts, 0, 99))
+>A : Symbol(A, Decl(thisTypeOptionalCall.ts, 0, 21))
+>R : Symbol(R, Decl(thisTypeOptionalCall.ts, 0, 38))
+
+    return fn?.bind(obj);
+>fn?.bind : Symbol(Function.bind, Decl(lib.es5.d.ts, --, --))
+>fn : Symbol(fn, Decl(thisTypeOptionalCall.ts, 0, 49))
+>bind : Symbol(Function.bind, Decl(lib.es5.d.ts, --, --))
+>obj : Symbol(obj, Decl(thisTypeOptionalCall.ts, 0, 42))
+}
diff --git a/tests/baselines/reference/thisTypeOptionalCall.types b/tests/baselines/reference/thisTypeOptionalCall.types
new file mode 100644
index 00000000000..1c2a9cd7020
--- /dev/null
+++ b/tests/baselines/reference/thisTypeOptionalCall.types
@@ -0,0 +1,16 @@
+=== tests/cases/conformance/types/thisType/thisTypeOptionalCall.ts ===
+function maybeBind<T, A extends any[], R>(obj: T, fn: ((this: T, ...args: A) => R) | undefined): ((...args: A) => R) | undefined {
+>maybeBind : <T, A extends any[], R>(obj: T, fn: ((this: T, ...args: A) => R) | undefined) => ((...args: A) => R) | undefined
+>obj : T
+>fn : ((this: T, ...args: A) => R) | undefined
+>this : T
+>args : A
+>args : A
+
+    return fn?.bind(obj);
+>fn?.bind(obj) : any
+>fn?.bind : ((this: Function, thisArg: any, ...argArray: any[]) => any) | undefined
+>fn : ((this: T, ...args: A) => R) | undefined
+>bind : ((this: Function, thisArg: any, ...argArray: any[]) => any) | undefined
+>obj : T
+}
diff --git a/tests/cases/conformance/types/thisType/thisTypeOptionalCall.ts b/tests/cases/conformance/types/thisType/thisTypeOptionalCall.ts
new file mode 100644
index 00000000000..b3f35a596ea
--- /dev/null
+++ b/tests/cases/conformance/types/thisType/thisTypeOptionalCall.ts
@@ -0,0 +1,8 @@
+// @strictNullChecks: true
+// @noImplicitAny: true
+// @noImplicitThis: true
+// @strictBindCallApply: false
+
+function maybeBind<T, A extends any[], R>(obj: T, fn: ((this: T, ...args: A) => R) | undefined): ((...args: A) => R) | undefined {
+    return fn?.bind(obj);
+}
\ No newline at end of file