diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index f30f8e9d00a42..ac599ae58cb99 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -791,6 +791,7 @@ namespace ts {
         const wildcardType = createIntrinsicType(TypeFlags.Any, "any");
         const errorType = createIntrinsicType(TypeFlags.Any, "error");
         const unresolvedType = createIntrinsicType(TypeFlags.Any, "unresolved");
+        const nonInferrableAnyType = createIntrinsicType(TypeFlags.Any, "any", ObjectFlags.ContainsWideningType);
         const intrinsicMarkerType = createIntrinsicType(TypeFlags.Any, "intrinsic");
         const unknownType = createIntrinsicType(TypeFlags.Unknown, "unknown");
         const nonNullUnknownType = createIntrinsicType(TypeFlags.Unknown, "unknown");
@@ -9560,7 +9561,11 @@ namespace ts {
             if (reportErrors && !declarationBelongsToPrivateAmbientMember(element)) {
                 reportImplicitAny(element, anyType);
             }
-            return anyType;
+            // When we're including the pattern in the type (an indication we're obtaining a contextual type), we
+            // use a non-inferrable any type. Inference will never directly infer this type, but it is possible
+            // to infer a type that contains it, e.g. for a binding pattern like [foo] or { foo }. In such cases,
+            // widening of the binding pattern type substitutes a regular any for the non-inferrable any.
+            return includePatternInType ? nonInferrableAnyType : anyType;
         }
 
         // Return the type implied by an object binding pattern
@@ -22657,7 +22662,10 @@ namespace ts {
                         //
                         // This flag is infectious; if we produce Box<never> (where never is silentNeverType), Box<never> is
                         // also non-inferrable.
-                        if (getObjectFlags(source) & ObjectFlags.NonInferrableType) {
+                        //
+                        // As a special case, also ignore nonInferrableAnyType, which is a special form of the any type
+                        // used as a stand-in for binding elements when they are being inferred.
+                        if (getObjectFlags(source) & ObjectFlags.NonInferrableType || source === nonInferrableAnyType) {
                             return;
                         }
                         if (!inference.isFixed) {
diff --git a/tests/baselines/reference/inferStringLiteralUnionForBindingElement.js b/tests/baselines/reference/inferStringLiteralUnionForBindingElement.js
new file mode 100644
index 0000000000000..e5c5527287a16
--- /dev/null
+++ b/tests/baselines/reference/inferStringLiteralUnionForBindingElement.js
@@ -0,0 +1,41 @@
+//// [inferStringLiteralUnionForBindingElement.ts]
+declare function func<T extends string>(arg: { keys: T[] }): { readonly keys: T[]; readonly firstKey: T; };
+
+function func1() {
+    const { firstKey } = func({keys: ["aa", "bb"]})
+    const a: "aa" | "bb" = firstKey;
+
+    const { keys } = func({keys: ["aa", "bb"]})
+    const b: ("aa" | "bb")[] = keys;
+}
+  
+function func2() {
+    const { keys, firstKey } = func({keys: ["aa", "bb"]})
+    const a: "aa" | "bb" = firstKey;
+    const b: ("aa" | "bb")[] = keys;
+}
+
+function func3() {
+    const x = func({keys: ["aa", "bb"]})
+    const a: "aa" | "bb" = x.firstKey;
+    const b: ("aa" | "bb")[] = x.keys;
+}
+
+
+//// [inferStringLiteralUnionForBindingElement.js]
+function func1() {
+    var firstKey = func({ keys: ["aa", "bb"] }).firstKey;
+    var a = firstKey;
+    var keys = func({ keys: ["aa", "bb"] }).keys;
+    var b = keys;
+}
+function func2() {
+    var _a = func({ keys: ["aa", "bb"] }), keys = _a.keys, firstKey = _a.firstKey;
+    var a = firstKey;
+    var b = keys;
+}
+function func3() {
+    var x = func({ keys: ["aa", "bb"] });
+    var a = x.firstKey;
+    var b = x.keys;
+}
diff --git a/tests/baselines/reference/inferStringLiteralUnionForBindingElement.symbols b/tests/baselines/reference/inferStringLiteralUnionForBindingElement.symbols
new file mode 100644
index 0000000000000..1b19c0132ce79
--- /dev/null
+++ b/tests/baselines/reference/inferStringLiteralUnionForBindingElement.symbols
@@ -0,0 +1,73 @@
+=== tests/cases/compiler/inferStringLiteralUnionForBindingElement.ts ===
+declare function func<T extends string>(arg: { keys: T[] }): { readonly keys: T[]; readonly firstKey: T; };
+>func : Symbol(func, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 0))
+>T : Symbol(T, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 22))
+>arg : Symbol(arg, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 40))
+>keys : Symbol(keys, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 46))
+>T : Symbol(T, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 22))
+>keys : Symbol(keys, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 62))
+>T : Symbol(T, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 22))
+>firstKey : Symbol(firstKey, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 82))
+>T : Symbol(T, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 22))
+
+function func1() {
+>func1 : Symbol(func1, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 107))
+
+    const { firstKey } = func({keys: ["aa", "bb"]})
+>firstKey : Symbol(firstKey, Decl(inferStringLiteralUnionForBindingElement.ts, 3, 11))
+>func : Symbol(func, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 0))
+>keys : Symbol(keys, Decl(inferStringLiteralUnionForBindingElement.ts, 3, 31))
+
+    const a: "aa" | "bb" = firstKey;
+>a : Symbol(a, Decl(inferStringLiteralUnionForBindingElement.ts, 4, 9))
+>firstKey : Symbol(firstKey, Decl(inferStringLiteralUnionForBindingElement.ts, 3, 11))
+
+    const { keys } = func({keys: ["aa", "bb"]})
+>keys : Symbol(keys, Decl(inferStringLiteralUnionForBindingElement.ts, 6, 11))
+>func : Symbol(func, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 0))
+>keys : Symbol(keys, Decl(inferStringLiteralUnionForBindingElement.ts, 6, 27))
+
+    const b: ("aa" | "bb")[] = keys;
+>b : Symbol(b, Decl(inferStringLiteralUnionForBindingElement.ts, 7, 9))
+>keys : Symbol(keys, Decl(inferStringLiteralUnionForBindingElement.ts, 6, 11))
+}
+  
+function func2() {
+>func2 : Symbol(func2, Decl(inferStringLiteralUnionForBindingElement.ts, 8, 1))
+
+    const { keys, firstKey } = func({keys: ["aa", "bb"]})
+>keys : Symbol(keys, Decl(inferStringLiteralUnionForBindingElement.ts, 11, 11))
+>firstKey : Symbol(firstKey, Decl(inferStringLiteralUnionForBindingElement.ts, 11, 17))
+>func : Symbol(func, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 0))
+>keys : Symbol(keys, Decl(inferStringLiteralUnionForBindingElement.ts, 11, 37))
+
+    const a: "aa" | "bb" = firstKey;
+>a : Symbol(a, Decl(inferStringLiteralUnionForBindingElement.ts, 12, 9))
+>firstKey : Symbol(firstKey, Decl(inferStringLiteralUnionForBindingElement.ts, 11, 17))
+
+    const b: ("aa" | "bb")[] = keys;
+>b : Symbol(b, Decl(inferStringLiteralUnionForBindingElement.ts, 13, 9))
+>keys : Symbol(keys, Decl(inferStringLiteralUnionForBindingElement.ts, 11, 11))
+}
+
+function func3() {
+>func3 : Symbol(func3, Decl(inferStringLiteralUnionForBindingElement.ts, 14, 1))
+
+    const x = func({keys: ["aa", "bb"]})
+>x : Symbol(x, Decl(inferStringLiteralUnionForBindingElement.ts, 17, 9))
+>func : Symbol(func, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 0))
+>keys : Symbol(keys, Decl(inferStringLiteralUnionForBindingElement.ts, 17, 20))
+
+    const a: "aa" | "bb" = x.firstKey;
+>a : Symbol(a, Decl(inferStringLiteralUnionForBindingElement.ts, 18, 9))
+>x.firstKey : Symbol(firstKey, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 82))
+>x : Symbol(x, Decl(inferStringLiteralUnionForBindingElement.ts, 17, 9))
+>firstKey : Symbol(firstKey, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 82))
+
+    const b: ("aa" | "bb")[] = x.keys;
+>b : Symbol(b, Decl(inferStringLiteralUnionForBindingElement.ts, 19, 9))
+>x.keys : Symbol(keys, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 62))
+>x : Symbol(x, Decl(inferStringLiteralUnionForBindingElement.ts, 17, 9))
+>keys : Symbol(keys, Decl(inferStringLiteralUnionForBindingElement.ts, 0, 62))
+}
+
diff --git a/tests/baselines/reference/inferStringLiteralUnionForBindingElement.types b/tests/baselines/reference/inferStringLiteralUnionForBindingElement.types
new file mode 100644
index 0000000000000..0d3cf898877f1
--- /dev/null
+++ b/tests/baselines/reference/inferStringLiteralUnionForBindingElement.types
@@ -0,0 +1,89 @@
+=== tests/cases/compiler/inferStringLiteralUnionForBindingElement.ts ===
+declare function func<T extends string>(arg: { keys: T[] }): { readonly keys: T[]; readonly firstKey: T; };
+>func : <T extends string>(arg: {    keys: T[];}) => {    readonly keys: T[];    readonly firstKey: T;}
+>arg : { keys: T[]; }
+>keys : T[]
+>keys : T[]
+>firstKey : T
+
+function func1() {
+>func1 : () => void
+
+    const { firstKey } = func({keys: ["aa", "bb"]})
+>firstKey : "aa" | "bb"
+>func({keys: ["aa", "bb"]}) : { readonly keys: ("aa" | "bb")[]; readonly firstKey: "aa" | "bb"; }
+>func : <T extends string>(arg: { keys: T[]; }) => { readonly keys: T[]; readonly firstKey: T; }
+>{keys: ["aa", "bb"]} : { keys: ("aa" | "bb")[]; }
+>keys : ("aa" | "bb")[]
+>["aa", "bb"] : ("aa" | "bb")[]
+>"aa" : "aa"
+>"bb" : "bb"
+
+    const a: "aa" | "bb" = firstKey;
+>a : "aa" | "bb"
+>firstKey : "aa" | "bb"
+
+    const { keys } = func({keys: ["aa", "bb"]})
+>keys : ("aa" | "bb")[]
+>func({keys: ["aa", "bb"]}) : { readonly keys: ("aa" | "bb")[]; readonly firstKey: "aa" | "bb"; }
+>func : <T extends string>(arg: { keys: T[]; }) => { readonly keys: T[]; readonly firstKey: T; }
+>{keys: ["aa", "bb"]} : { keys: ("aa" | "bb")[]; }
+>keys : ("aa" | "bb")[]
+>["aa", "bb"] : ("aa" | "bb")[]
+>"aa" : "aa"
+>"bb" : "bb"
+
+    const b: ("aa" | "bb")[] = keys;
+>b : ("aa" | "bb")[]
+>keys : ("aa" | "bb")[]
+}
+  
+function func2() {
+>func2 : () => void
+
+    const { keys, firstKey } = func({keys: ["aa", "bb"]})
+>keys : ("aa" | "bb")[]
+>firstKey : "aa" | "bb"
+>func({keys: ["aa", "bb"]}) : { readonly keys: ("aa" | "bb")[]; readonly firstKey: "aa" | "bb"; }
+>func : <T extends string>(arg: { keys: T[]; }) => { readonly keys: T[]; readonly firstKey: T; }
+>{keys: ["aa", "bb"]} : { keys: ("aa" | "bb")[]; }
+>keys : ("aa" | "bb")[]
+>["aa", "bb"] : ("aa" | "bb")[]
+>"aa" : "aa"
+>"bb" : "bb"
+
+    const a: "aa" | "bb" = firstKey;
+>a : "aa" | "bb"
+>firstKey : "aa" | "bb"
+
+    const b: ("aa" | "bb")[] = keys;
+>b : ("aa" | "bb")[]
+>keys : ("aa" | "bb")[]
+}
+
+function func3() {
+>func3 : () => void
+
+    const x = func({keys: ["aa", "bb"]})
+>x : { readonly keys: ("aa" | "bb")[]; readonly firstKey: "aa" | "bb"; }
+>func({keys: ["aa", "bb"]}) : { readonly keys: ("aa" | "bb")[]; readonly firstKey: "aa" | "bb"; }
+>func : <T extends string>(arg: { keys: T[]; }) => { readonly keys: T[]; readonly firstKey: T; }
+>{keys: ["aa", "bb"]} : { keys: ("aa" | "bb")[]; }
+>keys : ("aa" | "bb")[]
+>["aa", "bb"] : ("aa" | "bb")[]
+>"aa" : "aa"
+>"bb" : "bb"
+
+    const a: "aa" | "bb" = x.firstKey;
+>a : "aa" | "bb"
+>x.firstKey : "aa" | "bb"
+>x : { readonly keys: ("aa" | "bb")[]; readonly firstKey: "aa" | "bb"; }
+>firstKey : "aa" | "bb"
+
+    const b: ("aa" | "bb")[] = x.keys;
+>b : ("aa" | "bb")[]
+>x.keys : ("aa" | "bb")[]
+>x : { readonly keys: ("aa" | "bb")[]; readonly firstKey: "aa" | "bb"; }
+>keys : ("aa" | "bb")[]
+}
+
diff --git a/tests/cases/compiler/inferStringLiteralUnionForBindingElement.ts b/tests/cases/compiler/inferStringLiteralUnionForBindingElement.ts
new file mode 100644
index 0000000000000..0b8727ea5a0ce
--- /dev/null
+++ b/tests/cases/compiler/inferStringLiteralUnionForBindingElement.ts
@@ -0,0 +1,21 @@
+declare function func<T extends string>(arg: { keys: T[] }): { readonly keys: T[]; readonly firstKey: T; };
+
+function func1() {
+    const { firstKey } = func({keys: ["aa", "bb"]})
+    const a: "aa" | "bb" = firstKey;
+
+    const { keys } = func({keys: ["aa", "bb"]})
+    const b: ("aa" | "bb")[] = keys;
+}
+  
+function func2() {
+    const { keys, firstKey } = func({keys: ["aa", "bb"]})
+    const a: "aa" | "bb" = firstKey;
+    const b: ("aa" | "bb")[] = keys;
+}
+
+function func3() {
+    const x = func({keys: ["aa", "bb"]})
+    const a: "aa" | "bb" = x.firstKey;
+    const b: ("aa" | "bb")[] = x.keys;
+}