diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 508f6bb323706..4f80bcb783442 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -11460,7 +11460,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             // contextual type or, if the element itself is a binding pattern, with the type implied by that binding
             // pattern.
             const contextualType = isBindingPattern(element.name) ? getTypeFromBindingPattern(element.name, /*includePatternInType*/ true, /*reportErrors*/ false) : unknownType;
-            return addOptionality(widenTypeInferredFromInitializer(element, checkDeclarationInitializer(element, CheckMode.Normal, contextualType)));
+            return addOptionality(widenTypeInferredFromInitializer(element, checkDeclarationInitializer(element, reportErrors ? CheckMode.Normal : CheckMode.Contextual, contextualType)));
         }
         if (isBindingPattern(element.name)) {
             return getTypeFromBindingPattern(element.name, includePatternInType, reportErrors);
@@ -11618,16 +11618,16 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         return false;
     }
 
-    function getTypeOfVariableOrParameterOrProperty(symbol: Symbol): Type {
+    function getTypeOfVariableOrParameterOrProperty(symbol: Symbol, checkMode?: CheckMode): Type {
         const links = getSymbolLinks(symbol);
         if (!links.type) {
-            const type = getTypeOfVariableOrParameterOrPropertyWorker(symbol);
+            const type = getTypeOfVariableOrParameterOrPropertyWorker(symbol, checkMode);
             // For a contextually typed parameter it is possible that a type has already
             // been assigned (in assignTypeToParameterAndFixTypeParameters), and we want
             // to preserve this type. In fact, we need to _prefer_ that type, but it won't
             // be assigned until contextual typing is complete, so we need to defer in
             // cases where contextual typing may take place.
-            if (!links.type && !isParameterOfContextSensitiveSignature(symbol)) {
+            if (!links.type && !isParameterOfContextSensitiveSignature(symbol) && !checkMode) {
                 links.type = type;
             }
             return type;
@@ -11635,7 +11635,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         return links.type;
     }
 
-    function getTypeOfVariableOrParameterOrPropertyWorker(symbol: Symbol): Type {
+    function getTypeOfVariableOrParameterOrPropertyWorker(symbol: Symbol, checkMode?: CheckMode): Type {
         // Handle prototype property
         if (symbol.flags & SymbolFlags.Prototype) {
             return getTypeOfPrototypeProperty(symbol);
@@ -11678,6 +11678,16 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             if (symbol.flags & SymbolFlags.ValueModule && !(symbol.flags & SymbolFlags.Assignment)) {
                 return getTypeOfFuncClassEnumModule(symbol);
             }
+
+            // When trying to get the *contextual* type of a binding element, it's possible to fall in a loop and therefore
+            // end up in a circularity-like situation. This is not a true circularity so we should not report such an error.
+            // For example, here the looping could happen when trying to get the type of `a` (binding element):
+            //
+            //   const { a, b = a } = { a: 0 }
+            //
+            if (isBindingElement(declaration) && checkMode === CheckMode.Contextual) {
+                return errorType;
+            }
             return reportCircularityError(symbol);
         }
         let type: Type;
@@ -11750,6 +11760,16 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             if (symbol.flags & SymbolFlags.ValueModule && !(symbol.flags & SymbolFlags.Assignment)) {
                 return getTypeOfFuncClassEnumModule(symbol);
             }
+
+            // When trying to get the *contextual* type of a binding element, it's possible to fall in a loop and therefore
+            // end up in a circularity-like situation. This is not a true circularity so we should not report such an error.
+            // For example, here the looping could happen when trying to get the type of `a` (binding element):
+            //
+            //   const { a, b = a } = { a: 0 }
+            //
+            if (isBindingElement(declaration) && checkMode === CheckMode.Contextual) {
+                return type;
+            }
             return reportCircularityError(symbol);
         }
         return type;
@@ -12032,7 +12052,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         return getTypeOfSymbol(symbol);
     }
 
-    function getTypeOfSymbol(symbol: Symbol): Type {
+    function getTypeOfSymbol(symbol: Symbol, checkMode?: CheckMode): Type {
         const checkFlags = getCheckFlags(symbol);
         if (checkFlags & CheckFlags.DeferredType) {
             return getTypeOfSymbolWithDeferredType(symbol);
@@ -12047,7 +12067,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             return getTypeOfReverseMappedSymbol(symbol as ReverseMappedSymbol);
         }
         if (symbol.flags & (SymbolFlags.Variable | SymbolFlags.Property)) {
-            return getTypeOfVariableOrParameterOrProperty(symbol);
+            return getTypeOfVariableOrParameterOrProperty(symbol, checkMode);
         }
         if (symbol.flags & (SymbolFlags.Function | SymbolFlags.Method | SymbolFlags.Class | SymbolFlags.Enum | SymbolFlags.ValueModule)) {
             return getTypeOfFuncClassEnumModule(symbol);
@@ -29069,8 +29089,8 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         }
     }
 
-    function getNarrowedTypeOfSymbol(symbol: Symbol, location: Identifier) {
-        const type = getTypeOfSymbol(symbol);
+    function getNarrowedTypeOfSymbol(symbol: Symbol, location: Identifier, checkMode?: CheckMode) {
+        const type = getTypeOfSymbol(symbol, checkMode);
         const declaration = symbol.valueDeclaration;
         if (declaration) {
             // If we have a non-rest binding element with no initializer declared as a const variable or a const-like
@@ -29233,7 +29253,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
 
         checkNestedBlockScopedBinding(node, symbol);
 
-        let type = getNarrowedTypeOfSymbol(localOrExportSymbol, node);
+        let type = getNarrowedTypeOfSymbol(localOrExportSymbol, node, checkMode);
         const assignmentKind = getAssignmentTargetKind(node);
 
         if (assignmentKind) {
diff --git a/tests/baselines/reference/destructuringArrayBindingPatternAndAssignment3.types b/tests/baselines/reference/destructuringArrayBindingPatternAndAssignment3.types
index 72aaa6378e5af..791ba83c243dc 100644
--- a/tests/baselines/reference/destructuringArrayBindingPatternAndAssignment3.types
+++ b/tests/baselines/reference/destructuringArrayBindingPatternAndAssignment3.types
@@ -2,16 +2,16 @@
 
 === destructuringArrayBindingPatternAndAssignment3.ts ===
 const [a, b = a] = [1]; // ok
->a : any
->b : any
->a : any
+>a : number
+>b : number
+>a : number
 >[1] : [number]
 >1 : 1
 
 const [c, d = c, e = e] = [1]; // error for e = e
->c : any
->d : any
->c : any
+>c : number
+>d : number
+>c : number
 >e : any
 >e : any
 >[1] : [number]
diff --git a/tests/baselines/reference/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.js b/tests/baselines/reference/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.js
new file mode 100644
index 0000000000000..47eaab26cd17b
--- /dev/null
+++ b/tests/baselines/reference/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.js
@@ -0,0 +1,48 @@
+//// [tests/cases/conformance/es6/destructuring/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts] ////
+
+//// [destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts]
+// To be inferred as `number`
+function f1() {
+    const [a1, b1 = a1] = [1];
+    const [a2, b2 = 1 + a2] = [1];
+}
+
+// To be inferred as `string`
+function f2() {
+    const [a1, b1 = a1] = ['hi'];
+    const [a2, b2 = a2 + '!'] = ['hi'];
+}
+
+// To be inferred as `string | number`
+function f3() {
+    const [a1, b1 = a1] = ['hi', 1];
+    const [a2, b2 = a2 + '!'] = ['hi', 1];
+}
+
+// Based on comment:
+//   - https://github.com/microsoft/TypeScript/issues/49989#issuecomment-1852694486
+declare const yadda: [number, number] | undefined
+function f4() {
+    const [ a, b = a ] = yadda ?? [];
+}
+
+
+//// [destructuringArrayBindingPatternAndAssignment5SiblingInitializer.js]
+// To be inferred as `number`
+function f1() {
+    var _a = [1], a1 = _a[0], _b = _a[1], b1 = _b === void 0 ? a1 : _b;
+    var _c = [1], a2 = _c[0], _d = _c[1], b2 = _d === void 0 ? 1 + a2 : _d;
+}
+// To be inferred as `string`
+function f2() {
+    var _a = ['hi'], a1 = _a[0], _b = _a[1], b1 = _b === void 0 ? a1 : _b;
+    var _c = ['hi'], a2 = _c[0], _d = _c[1], b2 = _d === void 0 ? a2 + '!' : _d;
+}
+// To be inferred as `string | number`
+function f3() {
+    var _a = ['hi', 1], a1 = _a[0], _b = _a[1], b1 = _b === void 0 ? a1 : _b;
+    var _c = ['hi', 1], a2 = _c[0], _d = _c[1], b2 = _d === void 0 ? a2 + '!' : _d;
+}
+function f4() {
+    var _a = yadda !== null && yadda !== void 0 ? yadda : [], a = _a[0], _b = _a[1], b = _b === void 0 ? a : _b;
+}
diff --git a/tests/baselines/reference/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.symbols b/tests/baselines/reference/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.symbols
new file mode 100644
index 0000000000000..2ff79c20083f2
--- /dev/null
+++ b/tests/baselines/reference/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.symbols
@@ -0,0 +1,63 @@
+//// [tests/cases/conformance/es6/destructuring/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts] ////
+
+=== destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts ===
+// To be inferred as `number`
+function f1() {
+>f1 : Symbol(f1, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 0, 0))
+
+    const [a1, b1 = a1] = [1];
+>a1 : Symbol(a1, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 2, 11))
+>b1 : Symbol(b1, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 2, 14))
+>a1 : Symbol(a1, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 2, 11))
+
+    const [a2, b2 = 1 + a2] = [1];
+>a2 : Symbol(a2, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 3, 11))
+>b2 : Symbol(b2, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 3, 14))
+>a2 : Symbol(a2, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 3, 11))
+}
+
+// To be inferred as `string`
+function f2() {
+>f2 : Symbol(f2, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 4, 1))
+
+    const [a1, b1 = a1] = ['hi'];
+>a1 : Symbol(a1, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 8, 11))
+>b1 : Symbol(b1, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 8, 14))
+>a1 : Symbol(a1, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 8, 11))
+
+    const [a2, b2 = a2 + '!'] = ['hi'];
+>a2 : Symbol(a2, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 9, 11))
+>b2 : Symbol(b2, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 9, 14))
+>a2 : Symbol(a2, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 9, 11))
+}
+
+// To be inferred as `string | number`
+function f3() {
+>f3 : Symbol(f3, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 10, 1))
+
+    const [a1, b1 = a1] = ['hi', 1];
+>a1 : Symbol(a1, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 14, 11))
+>b1 : Symbol(b1, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 14, 14))
+>a1 : Symbol(a1, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 14, 11))
+
+    const [a2, b2 = a2 + '!'] = ['hi', 1];
+>a2 : Symbol(a2, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 15, 11))
+>b2 : Symbol(b2, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 15, 14))
+>a2 : Symbol(a2, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 15, 11))
+}
+
+// Based on comment:
+//   - https://github.com/microsoft/TypeScript/issues/49989#issuecomment-1852694486
+declare const yadda: [number, number] | undefined
+>yadda : Symbol(yadda, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 20, 13))
+
+function f4() {
+>f4 : Symbol(f4, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 20, 49))
+
+    const [ a, b = a ] = yadda ?? [];
+>a : Symbol(a, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 22, 11))
+>b : Symbol(b, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 22, 14))
+>a : Symbol(a, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 22, 11))
+>yadda : Symbol(yadda, Decl(destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts, 20, 13))
+}
+
diff --git a/tests/baselines/reference/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.types b/tests/baselines/reference/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.types
new file mode 100644
index 0000000000000..009a62ee2d987
--- /dev/null
+++ b/tests/baselines/reference/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.types
@@ -0,0 +1,85 @@
+//// [tests/cases/conformance/es6/destructuring/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts] ////
+
+=== destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts ===
+// To be inferred as `number`
+function f1() {
+>f1 : () => void
+
+    const [a1, b1 = a1] = [1];
+>a1 : number
+>b1 : number
+>a1 : number
+>[1] : [number]
+>1 : 1
+
+    const [a2, b2 = 1 + a2] = [1];
+>a2 : number
+>b2 : number
+>1 + a2 : number
+>1 : 1
+>a2 : number
+>[1] : [number]
+>1 : 1
+}
+
+// To be inferred as `string`
+function f2() {
+>f2 : () => void
+
+    const [a1, b1 = a1] = ['hi'];
+>a1 : string
+>b1 : string
+>a1 : string
+>['hi'] : [string]
+>'hi' : "hi"
+
+    const [a2, b2 = a2 + '!'] = ['hi'];
+>a2 : string
+>b2 : string
+>a2 + '!' : string
+>a2 : string
+>'!' : "!"
+>['hi'] : [string]
+>'hi' : "hi"
+}
+
+// To be inferred as `string | number`
+function f3() {
+>f3 : () => void
+
+    const [a1, b1 = a1] = ['hi', 1];
+>a1 : string
+>b1 : string | number
+>a1 : string
+>['hi', 1] : [string, number]
+>'hi' : "hi"
+>1 : 1
+
+    const [a2, b2 = a2 + '!'] = ['hi', 1];
+>a2 : string
+>b2 : string | number
+>a2 + '!' : string
+>a2 : string
+>'!' : "!"
+>['hi', 1] : [string, number]
+>'hi' : "hi"
+>1 : 1
+}
+
+// Based on comment:
+//   - https://github.com/microsoft/TypeScript/issues/49989#issuecomment-1852694486
+declare const yadda: [number, number] | undefined
+>yadda : [number, number]
+
+function f4() {
+>f4 : () => void
+
+    const [ a, b = a ] = yadda ?? [];
+>a : number
+>b : number
+>a : number
+>yadda ?? [] : [number, number] | []
+>yadda : [number, number]
+>[] : []
+}
+
diff --git a/tests/baselines/reference/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.js b/tests/baselines/reference/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.js
new file mode 100644
index 0000000000000..92a7a56842bfc
--- /dev/null
+++ b/tests/baselines/reference/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.js
@@ -0,0 +1,48 @@
+//// [tests/cases/conformance/es6/destructuring/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts] ////
+
+//// [destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts]
+// To be inferred as `number`
+function f1() {
+    const { a1, b1 = a1 } = { a1: 1 };
+    const { a2, b2 = 1 + a2 } = { a2: 1 };
+}
+
+// To be inferred as `string`
+function f2() {
+    const { a1, b1 = a1 } = { a1: 'hi' };
+    const { a2, b2 = a2 + '!' } = { a2: 'hi' };
+}
+
+// To be inferred as `string | number`
+function f3() {
+    const { a1, b1 = a1 } = { a1: 'hi', b1: 1 };
+    const { a2, b2 = a2 + '!' } = { a2: 'hi', b2: 1 };
+}
+
+// Based on comment:
+//   - https://github.com/microsoft/TypeScript/issues/49989#issuecomment-1852694486
+declare const yadda: { a?: number, b?: number } | undefined
+function f4() {
+    const { a, b = a } = yadda ?? {};
+}
+
+
+//// [destructuringObjectBindingPatternAndAssignment9SiblingInitializer.js]
+// To be inferred as `number`
+function f1() {
+    var _a = { a1: 1 }, a1 = _a.a1, _b = _a.b1, b1 = _b === void 0 ? a1 : _b;
+    var _c = { a2: 1 }, a2 = _c.a2, _d = _c.b2, b2 = _d === void 0 ? 1 + a2 : _d;
+}
+// To be inferred as `string`
+function f2() {
+    var _a = { a1: 'hi' }, a1 = _a.a1, _b = _a.b1, b1 = _b === void 0 ? a1 : _b;
+    var _c = { a2: 'hi' }, a2 = _c.a2, _d = _c.b2, b2 = _d === void 0 ? a2 + '!' : _d;
+}
+// To be inferred as `string | number`
+function f3() {
+    var _a = { a1: 'hi', b1: 1 }, a1 = _a.a1, _b = _a.b1, b1 = _b === void 0 ? a1 : _b;
+    var _c = { a2: 'hi', b2: 1 }, a2 = _c.a2, _d = _c.b2, b2 = _d === void 0 ? a2 + '!' : _d;
+}
+function f4() {
+    var _a = yadda !== null && yadda !== void 0 ? yadda : {}, a = _a.a, _b = _a.b, b = _b === void 0 ? a : _b;
+}
diff --git a/tests/baselines/reference/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.symbols b/tests/baselines/reference/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.symbols
new file mode 100644
index 0000000000000..3c76a5d2b045d
--- /dev/null
+++ b/tests/baselines/reference/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.symbols
@@ -0,0 +1,73 @@
+//// [tests/cases/conformance/es6/destructuring/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts] ////
+
+=== destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts ===
+// To be inferred as `number`
+function f1() {
+>f1 : Symbol(f1, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 0, 0))
+
+    const { a1, b1 = a1 } = { a1: 1 };
+>a1 : Symbol(a1, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 2, 11))
+>b1 : Symbol(b1, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 2, 15))
+>a1 : Symbol(a1, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 2, 11))
+>a1 : Symbol(a1, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 2, 29))
+
+    const { a2, b2 = 1 + a2 } = { a2: 1 };
+>a2 : Symbol(a2, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 3, 11))
+>b2 : Symbol(b2, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 3, 15))
+>a2 : Symbol(a2, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 3, 11))
+>a2 : Symbol(a2, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 3, 33))
+}
+
+// To be inferred as `string`
+function f2() {
+>f2 : Symbol(f2, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 4, 1))
+
+    const { a1, b1 = a1 } = { a1: 'hi' };
+>a1 : Symbol(a1, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 8, 11))
+>b1 : Symbol(b1, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 8, 15))
+>a1 : Symbol(a1, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 8, 11))
+>a1 : Symbol(a1, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 8, 29))
+
+    const { a2, b2 = a2 + '!' } = { a2: 'hi' };
+>a2 : Symbol(a2, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 9, 11))
+>b2 : Symbol(b2, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 9, 15))
+>a2 : Symbol(a2, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 9, 11))
+>a2 : Symbol(a2, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 9, 35))
+}
+
+// To be inferred as `string | number`
+function f3() {
+>f3 : Symbol(f3, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 10, 1))
+
+    const { a1, b1 = a1 } = { a1: 'hi', b1: 1 };
+>a1 : Symbol(a1, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 14, 11))
+>b1 : Symbol(b1, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 14, 15))
+>a1 : Symbol(a1, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 14, 11))
+>a1 : Symbol(a1, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 14, 29))
+>b1 : Symbol(b1, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 14, 39))
+
+    const { a2, b2 = a2 + '!' } = { a2: 'hi', b2: 1 };
+>a2 : Symbol(a2, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 15, 11))
+>b2 : Symbol(b2, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 15, 15))
+>a2 : Symbol(a2, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 15, 11))
+>a2 : Symbol(a2, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 15, 35))
+>b2 : Symbol(b2, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 15, 45))
+}
+
+// Based on comment:
+//   - https://github.com/microsoft/TypeScript/issues/49989#issuecomment-1852694486
+declare const yadda: { a?: number, b?: number } | undefined
+>yadda : Symbol(yadda, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 20, 13))
+>a : Symbol(a, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 20, 22))
+>b : Symbol(b, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 20, 34))
+
+function f4() {
+>f4 : Symbol(f4, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 20, 59))
+
+    const { a, b = a } = yadda ?? {};
+>a : Symbol(a, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 22, 11))
+>b : Symbol(b, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 22, 14))
+>a : Symbol(a, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 22, 11))
+>yadda : Symbol(yadda, Decl(destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts, 20, 13))
+}
+
diff --git a/tests/baselines/reference/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.types b/tests/baselines/reference/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.types
new file mode 100644
index 0000000000000..c5ebaabe82453
--- /dev/null
+++ b/tests/baselines/reference/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.types
@@ -0,0 +1,95 @@
+//// [tests/cases/conformance/es6/destructuring/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts] ////
+
+=== destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts ===
+// To be inferred as `number`
+function f1() {
+>f1 : () => void
+
+    const { a1, b1 = a1 } = { a1: 1 };
+>a1 : number
+>b1 : number
+>a1 : number
+>{ a1: 1 } : { a1: number; b1?: number; }
+>a1 : number
+>1 : 1
+
+    const { a2, b2 = 1 + a2 } = { a2: 1 };
+>a2 : number
+>b2 : number
+>1 + a2 : number
+>1 : 1
+>a2 : number
+>{ a2: 1 } : { a2: number; b2?: number; }
+>a2 : number
+>1 : 1
+}
+
+// To be inferred as `string`
+function f2() {
+>f2 : () => void
+
+    const { a1, b1 = a1 } = { a1: 'hi' };
+>a1 : string
+>b1 : string
+>a1 : string
+>{ a1: 'hi' } : { a1: string; b1?: string; }
+>a1 : string
+>'hi' : "hi"
+
+    const { a2, b2 = a2 + '!' } = { a2: 'hi' };
+>a2 : string
+>b2 : string
+>a2 + '!' : string
+>a2 : string
+>'!' : "!"
+>{ a2: 'hi' } : { a2: string; b2?: string; }
+>a2 : string
+>'hi' : "hi"
+}
+
+// To be inferred as `string | number`
+function f3() {
+>f3 : () => void
+
+    const { a1, b1 = a1 } = { a1: 'hi', b1: 1 };
+>a1 : string
+>b1 : string | number
+>a1 : string
+>{ a1: 'hi', b1: 1 } : { a1: string; b1?: number; }
+>a1 : string
+>'hi' : "hi"
+>b1 : number
+>1 : 1
+
+    const { a2, b2 = a2 + '!' } = { a2: 'hi', b2: 1 };
+>a2 : string
+>b2 : string | number
+>a2 + '!' : string
+>a2 : string
+>'!' : "!"
+>{ a2: 'hi', b2: 1 } : { a2: string; b2?: number; }
+>a2 : string
+>'hi' : "hi"
+>b2 : number
+>1 : 1
+}
+
+// Based on comment:
+//   - https://github.com/microsoft/TypeScript/issues/49989#issuecomment-1852694486
+declare const yadda: { a?: number, b?: number } | undefined
+>yadda : { a?: number; b?: number; }
+>a : number
+>b : number
+
+function f4() {
+>f4 : () => void
+
+    const { a, b = a } = yadda ?? {};
+>a : number
+>b : number
+>a : number
+>yadda ?? {} : { a?: number; b?: number; }
+>yadda : { a?: number; b?: number; }
+>{} : {}
+}
+
diff --git a/tests/cases/conformance/es6/destructuring/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts b/tests/cases/conformance/es6/destructuring/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts
new file mode 100644
index 0000000000000..6183e22b61fbf
--- /dev/null
+++ b/tests/cases/conformance/es6/destructuring/destructuringArrayBindingPatternAndAssignment5SiblingInitializer.ts
@@ -0,0 +1,26 @@
+// @noImplicitAny: true
+
+// To be inferred as `number`
+function f1() {
+    const [a1, b1 = a1] = [1];
+    const [a2, b2 = 1 + a2] = [1];
+}
+
+// To be inferred as `string`
+function f2() {
+    const [a1, b1 = a1] = ['hi'];
+    const [a2, b2 = a2 + '!'] = ['hi'];
+}
+
+// To be inferred as `string | number`
+function f3() {
+    const [a1, b1 = a1] = ['hi', 1];
+    const [a2, b2 = a2 + '!'] = ['hi', 1];
+}
+
+// Based on comment:
+//   - https://github.com/microsoft/TypeScript/issues/49989#issuecomment-1852694486
+declare const yadda: [number, number] | undefined
+function f4() {
+    const [ a, b = a ] = yadda ?? [];
+}
diff --git a/tests/cases/conformance/es6/destructuring/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts b/tests/cases/conformance/es6/destructuring/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts
new file mode 100644
index 0000000000000..d4d5cd7c6cd4d
--- /dev/null
+++ b/tests/cases/conformance/es6/destructuring/destructuringObjectBindingPatternAndAssignment9SiblingInitializer.ts
@@ -0,0 +1,26 @@
+// @noImplicitAny: true
+
+// To be inferred as `number`
+function f1() {
+    const { a1, b1 = a1 } = { a1: 1 };
+    const { a2, b2 = 1 + a2 } = { a2: 1 };
+}
+
+// To be inferred as `string`
+function f2() {
+    const { a1, b1 = a1 } = { a1: 'hi' };
+    const { a2, b2 = a2 + '!' } = { a2: 'hi' };
+}
+
+// To be inferred as `string | number`
+function f3() {
+    const { a1, b1 = a1 } = { a1: 'hi', b1: 1 };
+    const { a2, b2 = a2 + '!' } = { a2: 'hi', b2: 1 };
+}
+
+// Based on comment:
+//   - https://github.com/microsoft/TypeScript/issues/49989#issuecomment-1852694486
+declare const yadda: { a?: number, b?: number } | undefined
+function f4() {
+    const { a, b = a } = yadda ?? {};
+}