diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index e3350d48bdf7a..860e8135b5d2c 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -11906,7 +11906,7 @@ 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(getWidenedLiteralTypeForInitializer(element, checkDeclarationInitializer(element, CheckMode.Normal, contextualType)));
         }
         if (isBindingPattern(element.name)) {
             return getTypeFromBindingPattern(element.name, includePatternInType, reportErrors);
@@ -40500,7 +40500,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
     }
 
     function widenTypeInferredFromInitializer(declaration: HasExpressionInitializer, type: Type) {
-        const widened = getCombinedNodeFlagsCached(declaration) & NodeFlags.Constant || isDeclarationReadonly(declaration) ? type : getWidenedLiteralType(type);
+        const widened = getWidenedLiteralTypeForInitializer(declaration, type);
         if (isInJSFile(declaration)) {
             if (isEmptyLiteralType(widened)) {
                 reportImplicitAny(declaration, anyType);
@@ -40514,6 +40514,10 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         return widened;
     }
 
+    function getWidenedLiteralTypeForInitializer(declaration: HasExpressionInitializer, type: Type) {
+        return getCombinedNodeFlagsCached(declaration) & NodeFlags.Constant || isDeclarationReadonly(declaration) ? type : getWidenedLiteralType(type);
+    }
+
     function isLiteralOfContextualType(candidateType: Type, contextualType: Type | undefined): boolean {
         if (contextualType) {
             if (contextualType.flags & TypeFlags.UnionOrIntersection) {
diff --git a/tests/baselines/reference/destructuringParameterDeclaration10(strict=false).symbols b/tests/baselines/reference/destructuringParameterDeclaration10(strict=false).symbols
new file mode 100644
index 0000000000000..a0da095b3f6de
--- /dev/null
+++ b/tests/baselines/reference/destructuringParameterDeclaration10(strict=false).symbols
@@ -0,0 +1,61 @@
+//// [tests/cases/conformance/es6/destructuring/destructuringParameterDeclaration10.ts] ////
+
+=== destructuringParameterDeclaration10.ts ===
+export function prepareConfig({
+>prepareConfig : Symbol(prepareConfig, Decl(destructuringParameterDeclaration10.ts, 0, 0))
+
+    additionalFiles: {
+>additionalFiles : Symbol(additionalFiles, Decl(destructuringParameterDeclaration10.ts, 4, 4))
+
+        json = []
+>json : Symbol(json, Decl(destructuringParameterDeclaration10.ts, 1, 22))
+
+    } = {}
+}: {
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+>additionalFiles : Symbol(additionalFiles, Decl(destructuringParameterDeclaration10.ts, 4, 4))
+>Partial : Symbol(Partial, Decl(lib.es5.d.ts, --, --))
+>Record : Symbol(Record, Decl(lib.es5.d.ts, --, --))
+
+} = {}) {
+    json // string[]
+>json : Symbol(json, Decl(destructuringParameterDeclaration10.ts, 1, 22))
+}
+
+export function prepareConfigWithoutAnnotation({
+>prepareConfigWithoutAnnotation : Symbol(prepareConfigWithoutAnnotation, Decl(destructuringParameterDeclaration10.ts, 8, 1))
+
+    additionalFiles: {
+>additionalFiles : Symbol(additionalFiles)
+
+        json = []
+>json : Symbol(json, Decl(destructuringParameterDeclaration10.ts, 11, 22))
+
+    } = {}
+} = {}) {
+    json
+>json : Symbol(json, Decl(destructuringParameterDeclaration10.ts, 11, 22))
+}
+
+export const prepareConfigWithContextualSignature: (param:{
+>prepareConfigWithContextualSignature : Symbol(prepareConfigWithContextualSignature, Decl(destructuringParameterDeclaration10.ts, 18, 12))
+>param : Symbol(param, Decl(destructuringParameterDeclaration10.ts, 18, 52))
+
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+>additionalFiles : Symbol(additionalFiles, Decl(destructuringParameterDeclaration10.ts, 18, 59))
+>Partial : Symbol(Partial, Decl(lib.es5.d.ts, --, --))
+>Record : Symbol(Record, Decl(lib.es5.d.ts, --, --))
+
+}) => void = ({
+    additionalFiles: {
+>additionalFiles : Symbol(additionalFiles, Decl(destructuringParameterDeclaration10.ts, 18, 59))
+
+        json = []
+>json : Symbol(json, Decl(destructuringParameterDeclaration10.ts, 21, 22))
+
+    } = {}
+} = {}) => {
+    json // string[]
+>json : Symbol(json, Decl(destructuringParameterDeclaration10.ts, 21, 22))
+}
+
diff --git a/tests/baselines/reference/destructuringParameterDeclaration10(strict=false).types b/tests/baselines/reference/destructuringParameterDeclaration10(strict=false).types
new file mode 100644
index 0000000000000..721d45fc041df
--- /dev/null
+++ b/tests/baselines/reference/destructuringParameterDeclaration10(strict=false).types
@@ -0,0 +1,99 @@
+//// [tests/cases/conformance/es6/destructuring/destructuringParameterDeclaration10.ts] ////
+
+=== destructuringParameterDeclaration10.ts ===
+export function prepareConfig({
+>prepareConfig : ({ additionalFiles: { json } }?: { additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>; }) => void
+>              : ^                             ^^^                                                                            ^^^^^^^^^
+
+    additionalFiles: {
+>additionalFiles : any
+>                : ^^^
+
+        json = []
+>json : string[]
+>     : ^^^^^^^^
+>[] : undefined[]
+>   : ^^^^^^^^^^^
+
+    } = {}
+>{} : {}
+>   : ^^
+
+}: {
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+>additionalFiles : Partial<Record<"json" | "jsonc" | "json5", string[]>>
+>                : ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+
+} = {}) {
+>{} : {}
+>   : ^^
+
+    json // string[]
+>json : string[]
+>     : ^^^^^^^^
+}
+
+export function prepareConfigWithoutAnnotation({
+>prepareConfigWithoutAnnotation : ({ additionalFiles: { json } }?: { additionalFiles?: { json?: any[]; }; }) => void
+>                               : ^                             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+
+    additionalFiles: {
+>additionalFiles : any
+>                : ^^^
+
+        json = []
+>json : any[]
+>     : ^^^^^
+>[] : undefined[]
+>   : ^^^^^^^^^^^
+
+    } = {}
+>{} : {}
+>   : ^^
+
+} = {}) {
+>{} : {}
+>   : ^^
+
+    json
+>json : any[]
+>     : ^^^^^
+}
+
+export const prepareConfigWithContextualSignature: (param:{
+>prepareConfigWithContextualSignature : (param: { additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>; }) => void
+>                                     : ^     ^^                                                                            ^^^^^    
+>param : { additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>; }
+>      : ^^^^^^^^^^^^^^^^^^^^                                                     ^^^
+
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+>additionalFiles : Partial<Record<"json" | "jsonc" | "json5", string[]>>
+>                : ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+
+}) => void = ({
+>({    additionalFiles: {        json = []    } = {}} = {}) => {    json // string[]} : ({ additionalFiles: { json } }?: { additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>; }) => void
+>                                                                                     : ^                             ^^^^^^^^^^^^^^^^^^^^^^^                                                     ^^^^^^^^^^^^
+
+    additionalFiles: {
+>additionalFiles : any
+>                : ^^^
+
+        json = []
+>json : string[]
+>     : ^^^^^^^^
+>[] : undefined[]
+>   : ^^^^^^^^^^^
+
+    } = {}
+>{} : {}
+>   : ^^
+
+} = {}) => {
+>{} : {}
+>   : ^^
+
+    json // string[]
+>json : string[]
+>     : ^^^^^^^^
+}
+
diff --git a/tests/baselines/reference/destructuringParameterDeclaration10(strict=true).symbols b/tests/baselines/reference/destructuringParameterDeclaration10(strict=true).symbols
new file mode 100644
index 0000000000000..a0da095b3f6de
--- /dev/null
+++ b/tests/baselines/reference/destructuringParameterDeclaration10(strict=true).symbols
@@ -0,0 +1,61 @@
+//// [tests/cases/conformance/es6/destructuring/destructuringParameterDeclaration10.ts] ////
+
+=== destructuringParameterDeclaration10.ts ===
+export function prepareConfig({
+>prepareConfig : Symbol(prepareConfig, Decl(destructuringParameterDeclaration10.ts, 0, 0))
+
+    additionalFiles: {
+>additionalFiles : Symbol(additionalFiles, Decl(destructuringParameterDeclaration10.ts, 4, 4))
+
+        json = []
+>json : Symbol(json, Decl(destructuringParameterDeclaration10.ts, 1, 22))
+
+    } = {}
+}: {
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+>additionalFiles : Symbol(additionalFiles, Decl(destructuringParameterDeclaration10.ts, 4, 4))
+>Partial : Symbol(Partial, Decl(lib.es5.d.ts, --, --))
+>Record : Symbol(Record, Decl(lib.es5.d.ts, --, --))
+
+} = {}) {
+    json // string[]
+>json : Symbol(json, Decl(destructuringParameterDeclaration10.ts, 1, 22))
+}
+
+export function prepareConfigWithoutAnnotation({
+>prepareConfigWithoutAnnotation : Symbol(prepareConfigWithoutAnnotation, Decl(destructuringParameterDeclaration10.ts, 8, 1))
+
+    additionalFiles: {
+>additionalFiles : Symbol(additionalFiles)
+
+        json = []
+>json : Symbol(json, Decl(destructuringParameterDeclaration10.ts, 11, 22))
+
+    } = {}
+} = {}) {
+    json
+>json : Symbol(json, Decl(destructuringParameterDeclaration10.ts, 11, 22))
+}
+
+export const prepareConfigWithContextualSignature: (param:{
+>prepareConfigWithContextualSignature : Symbol(prepareConfigWithContextualSignature, Decl(destructuringParameterDeclaration10.ts, 18, 12))
+>param : Symbol(param, Decl(destructuringParameterDeclaration10.ts, 18, 52))
+
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+>additionalFiles : Symbol(additionalFiles, Decl(destructuringParameterDeclaration10.ts, 18, 59))
+>Partial : Symbol(Partial, Decl(lib.es5.d.ts, --, --))
+>Record : Symbol(Record, Decl(lib.es5.d.ts, --, --))
+
+}) => void = ({
+    additionalFiles: {
+>additionalFiles : Symbol(additionalFiles, Decl(destructuringParameterDeclaration10.ts, 18, 59))
+
+        json = []
+>json : Symbol(json, Decl(destructuringParameterDeclaration10.ts, 21, 22))
+
+    } = {}
+} = {}) => {
+    json // string[]
+>json : Symbol(json, Decl(destructuringParameterDeclaration10.ts, 21, 22))
+}
+
diff --git a/tests/baselines/reference/destructuringParameterDeclaration10(strict=true).types b/tests/baselines/reference/destructuringParameterDeclaration10(strict=true).types
new file mode 100644
index 0000000000000..6eabd387b0b59
--- /dev/null
+++ b/tests/baselines/reference/destructuringParameterDeclaration10(strict=true).types
@@ -0,0 +1,99 @@
+//// [tests/cases/conformance/es6/destructuring/destructuringParameterDeclaration10.ts] ////
+
+=== destructuringParameterDeclaration10.ts ===
+export function prepareConfig({
+>prepareConfig : ({ additionalFiles: { json } }?: { additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>; }) => void
+>              : ^                             ^^^                                                                            ^^^^^^^^^
+
+    additionalFiles: {
+>additionalFiles : any
+>                : ^^^
+
+        json = []
+>json : string[]
+>     : ^^^^^^^^
+>[] : never[]
+>   : ^^^^^^^
+
+    } = {}
+>{} : {}
+>   : ^^
+
+}: {
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+>additionalFiles : Partial<Record<"json" | "jsonc" | "json5", string[]>> | undefined
+>                : ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+
+} = {}) {
+>{} : {}
+>   : ^^
+
+    json // string[]
+>json : string[]
+>     : ^^^^^^^^
+}
+
+export function prepareConfigWithoutAnnotation({
+>prepareConfigWithoutAnnotation : ({ additionalFiles: { json } }?: { additionalFiles?: { json?: never[] | undefined; } | undefined; }) => void
+>                               : ^                             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+
+    additionalFiles: {
+>additionalFiles : any
+>                : ^^^
+
+        json = []
+>json : never[]
+>     : ^^^^^^^
+>[] : never[]
+>   : ^^^^^^^
+
+    } = {}
+>{} : {}
+>   : ^^
+
+} = {}) {
+>{} : {}
+>   : ^^
+
+    json
+>json : never[]
+>     : ^^^^^^^
+}
+
+export const prepareConfigWithContextualSignature: (param:{
+>prepareConfigWithContextualSignature : (param: { additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>; }) => void
+>                                     : ^     ^^                                                                            ^^^^^    
+>param : { additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>; }
+>      : ^^^^^^^^^^^^^^^^^^^^                                                     ^^^
+
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+>additionalFiles : Partial<Record<"json" | "jsonc" | "json5", string[]>> | undefined
+>                : ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+
+}) => void = ({
+>({    additionalFiles: {        json = []    } = {}} = {}) => {    json // string[]} : ({ additionalFiles: { json } }?: { additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>; }) => void
+>                                                                                     : ^                             ^^^^^^^^^^^^^^^^^^^^^^^                                                     ^^^^^^^^^^^^
+
+    additionalFiles: {
+>additionalFiles : any
+>                : ^^^
+
+        json = []
+>json : string[]
+>     : ^^^^^^^^
+>[] : never[]
+>   : ^^^^^^^
+
+    } = {}
+>{} : {}
+>   : ^^
+
+} = {}) => {
+>{} : {}
+>   : ^^
+
+    json // string[]
+>json : string[]
+>     : ^^^^^^^^
+}
+
diff --git a/tests/baselines/reference/destructuringParameterDeclaration9(strict=false).symbols b/tests/baselines/reference/destructuringParameterDeclaration9(strict=false).symbols
new file mode 100644
index 0000000000000..da7a5cc68b4bb
--- /dev/null
+++ b/tests/baselines/reference/destructuringParameterDeclaration9(strict=false).symbols
@@ -0,0 +1,74 @@
+//// [tests/cases/conformance/es6/destructuring/destructuringParameterDeclaration9.ts] ////
+
+=== index.js ===
+/**
+ * @param {Object} [config]
+ * @param {Partial<Record<'json' | 'jsonc' | 'json5', string[]>>} [config.additionalFiles]
+ */
+export function prepareConfig({
+>prepareConfig : Symbol(prepareConfig, Decl(index.js, 0, 0))
+
+    additionalFiles: {
+>additionalFiles : Symbol(additionalFiles, Decl(index.js, 2, 3))
+
+        json = []
+>json : Symbol(json, Decl(index.js, 5, 22))
+
+    } = {}
+} = {}) {
+    json // string[]
+>json : Symbol(json, Decl(index.js, 5, 22))
+}
+
+export function prepareConfigWithoutAnnotation({
+>prepareConfigWithoutAnnotation : Symbol(prepareConfigWithoutAnnotation, Decl(index.js, 10, 1))
+
+    additionalFiles: {
+>additionalFiles : Symbol(additionalFiles)
+
+        json = []
+>json : Symbol(json, Decl(index.js, 13, 22))
+
+    } = {}
+} = {}) {
+    json
+>json : Symbol(json, Decl(index.js, 13, 22))
+}
+
+/** @type {(param: {
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+}) => void} */
+export const prepareConfigWithContextualSignature = ({
+>prepareConfigWithContextualSignature : Symbol(prepareConfigWithContextualSignature, Decl(index.js, 23, 12))
+
+    additionalFiles: {
+>additionalFiles : Symbol(additionalFiles, Decl(index.js, 20, 20))
+
+        json = []
+>json : Symbol(json, Decl(index.js, 24, 22))
+
+    } = {}
+} = {})=>  {
+    json // string[]
+>json : Symbol(json, Decl(index.js, 24, 22))
+}
+
+// Additional repros from https://github.com/microsoft/TypeScript/issues/59936
+
+/**
+ * @param {{ a?: { json?: string[] }}} [config]
+ */
+function f1({ a: { json = [] } = {} } = {}) { return json }
+>f1 : Symbol(f1, Decl(index.js, 29, 1))
+>a : Symbol(a, Decl(index.js, 34, 12))
+>json : Symbol(json, Decl(index.js, 36, 18))
+>json : Symbol(json, Decl(index.js, 36, 18))
+
+/**
+ * @param {[[string[]?]?]} [x]
+ */
+function f2([[json = []] = []] = []) { return json }
+>f2 : Symbol(f2, Decl(index.js, 36, 59))
+>json : Symbol(json, Decl(index.js, 41, 14))
+>json : Symbol(json, Decl(index.js, 41, 14))
+
diff --git a/tests/baselines/reference/destructuringParameterDeclaration9(strict=false).types b/tests/baselines/reference/destructuringParameterDeclaration9(strict=false).types
new file mode 100644
index 0000000000000..e827977063d76
--- /dev/null
+++ b/tests/baselines/reference/destructuringParameterDeclaration9(strict=false).types
@@ -0,0 +1,131 @@
+//// [tests/cases/conformance/es6/destructuring/destructuringParameterDeclaration9.ts] ////
+
+=== index.js ===
+/**
+ * @param {Object} [config]
+ * @param {Partial<Record<'json' | 'jsonc' | 'json5', string[]>>} [config.additionalFiles]
+ */
+export function prepareConfig({
+>prepareConfig : ({ additionalFiles: { json } }?: {    additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;}) => void
+>              : ^                             ^^^                    ^^^                                                     ^ ^^^^^^^^^
+
+    additionalFiles: {
+>additionalFiles : any
+>                : ^^^
+
+        json = []
+>json : string[]
+>     : ^^^^^^^^
+>[] : undefined[]
+>   : ^^^^^^^^^^^
+
+    } = {}
+>{} : {}
+>   : ^^
+
+} = {}) {
+>{} : {}
+>   : ^^
+
+    json // string[]
+>json : string[]
+>     : ^^^^^^^^
+}
+
+export function prepareConfigWithoutAnnotation({
+>prepareConfigWithoutAnnotation : ({ additionalFiles: { json } }?: { additionalFiles?: { json?: any[]; }; }) => void
+>                               : ^                             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+
+    additionalFiles: {
+>additionalFiles : any
+>                : ^^^
+
+        json = []
+>json : any[]
+>     : ^^^^^
+>[] : undefined[]
+>   : ^^^^^^^^^^^
+
+    } = {}
+>{} : {}
+>   : ^^
+
+} = {}) {
+>{} : {}
+>   : ^^
+
+    json
+>json : any[]
+>     : ^^^^^
+}
+
+/** @type {(param: {
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+}) => void} */
+export const prepareConfigWithContextualSignature = ({
+>prepareConfigWithContextualSignature : (param: { additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>; }) => void
+>                                     : ^     ^^                                                                            ^^^^^    
+>({    additionalFiles: {        json = []    } = {}} = {})=>  {    json // string[]} : ({ additionalFiles: { json } }?: { additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>; }) => void
+>                                                                                     : ^                             ^^^^^^^^^^^^^^^^^^^^^^^                                                     ^^^^^^^^    
+
+    additionalFiles: {
+>additionalFiles : any
+>                : ^^^
+
+        json = []
+>json : string[]
+>     : ^^^^^^^^
+>[] : undefined[]
+>   : ^^^^^^^^^^^
+
+    } = {}
+>{} : {}
+>   : ^^
+
+} = {})=>  {
+>{} : {}
+>   : ^^
+
+    json // string[]
+>json : string[]
+>     : ^^^^^^^^
+}
+
+// Additional repros from https://github.com/microsoft/TypeScript/issues/59936
+
+/**
+ * @param {{ a?: { json?: string[] }}} [config]
+ */
+function f1({ a: { json = [] } = {} } = {}) { return json }
+>f1 : ({ a: { json } }?: { a?: { json?: string[]; }; }) => string[]
+>   : ^               ^^^                             ^^^^^^^^^^^^^
+>a : any
+>  : ^^^
+>json : string[]
+>     : ^^^^^^^^
+>[] : undefined[]
+>   : ^^^^^^^^^^^
+>{} : {}
+>   : ^^
+>{} : {}
+>   : ^^
+>json : string[]
+>     : ^^^^^^^^
+
+/**
+ * @param {[[string[]?]?]} [x]
+ */
+function f2([[json = []] = []] = []) { return json }
+>f2 : ([[json]]?: [[string[]?]?]) => string[]
+>   : ^        ^^^              ^^^^^^^^^^^^^
+>json : string[]
+>     : ^^^^^^^^
+>[] : undefined[]
+>   : ^^^^^^^^^^^
+>[] : []
+>   : ^^
+>[] : []
+>   : ^^
+>json : string[]
+>     : ^^^^^^^^
+
diff --git a/tests/baselines/reference/destructuringParameterDeclaration9(strict=true).errors.txt b/tests/baselines/reference/destructuringParameterDeclaration9(strict=true).errors.txt
new file mode 100644
index 0000000000000..6f0315e55926d
--- /dev/null
+++ b/tests/baselines/reference/destructuringParameterDeclaration9(strict=true).errors.txt
@@ -0,0 +1,49 @@
+index.js(15,9): error TS7031: Binding element 'json' implicitly has an 'any[]' type.
+
+
+==== index.js (1 errors) ====
+    /**
+     * @param {Object} [config]
+     * @param {Partial<Record<'json' | 'jsonc' | 'json5', string[]>>} [config.additionalFiles]
+     */
+    export function prepareConfig({
+        additionalFiles: {
+            json = []
+        } = {}
+    } = {}) {
+        json // string[]
+    }
+    
+    export function prepareConfigWithoutAnnotation({
+        additionalFiles: {
+            json = []
+            ~~~~
+!!! error TS7031: Binding element 'json' implicitly has an 'any[]' type.
+        } = {}
+    } = {}) {
+        json
+    }
+    
+    /** @type {(param: {
+      additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+    }) => void} */
+    export const prepareConfigWithContextualSignature = ({
+        additionalFiles: {
+            json = []
+        } = {}
+    } = {})=>  {
+        json // string[]
+    }
+    
+    // Additional repros from https://github.com/microsoft/TypeScript/issues/59936
+    
+    /**
+     * @param {{ a?: { json?: string[] }}} [config]
+     */
+    function f1({ a: { json = [] } = {} } = {}) { return json }
+    
+    /**
+     * @param {[[string[]?]?]} [x]
+     */
+    function f2([[json = []] = []] = []) { return json }
+    
\ No newline at end of file
diff --git a/tests/baselines/reference/destructuringParameterDeclaration9(strict=true).symbols b/tests/baselines/reference/destructuringParameterDeclaration9(strict=true).symbols
new file mode 100644
index 0000000000000..648e03984cab4
--- /dev/null
+++ b/tests/baselines/reference/destructuringParameterDeclaration9(strict=true).symbols
@@ -0,0 +1,71 @@
+//// [tests/cases/conformance/es6/destructuring/destructuringParameterDeclaration9.ts] ////
+
+=== index.js ===
+/**
+ * @param {Object} [config]
+ * @param {Partial<Record<'json' | 'jsonc' | 'json5', string[]>>} [config.additionalFiles]
+ */
+export function prepareConfig({
+>prepareConfig : Symbol(prepareConfig, Decl(index.js, 0, 0))
+
+    additionalFiles: {
+        json = []
+>json : Symbol(json, Decl(index.js, 5, 22))
+
+    } = {}
+} = {}) {
+    json // string[]
+>json : Symbol(json, Decl(index.js, 5, 22))
+}
+
+export function prepareConfigWithoutAnnotation({
+>prepareConfigWithoutAnnotation : Symbol(prepareConfigWithoutAnnotation, Decl(index.js, 10, 1))
+
+    additionalFiles: {
+>additionalFiles : Symbol(additionalFiles)
+
+        json = []
+>json : Symbol(json, Decl(index.js, 13, 22))
+
+    } = {}
+} = {}) {
+    json
+>json : Symbol(json, Decl(index.js, 13, 22))
+}
+
+/** @type {(param: {
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+}) => void} */
+export const prepareConfigWithContextualSignature = ({
+>prepareConfigWithContextualSignature : Symbol(prepareConfigWithContextualSignature, Decl(index.js, 23, 12))
+
+    additionalFiles: {
+>additionalFiles : Symbol(additionalFiles, Decl(index.js, 20, 20))
+
+        json = []
+>json : Symbol(json, Decl(index.js, 24, 22))
+
+    } = {}
+} = {})=>  {
+    json // string[]
+>json : Symbol(json, Decl(index.js, 24, 22))
+}
+
+// Additional repros from https://github.com/microsoft/TypeScript/issues/59936
+
+/**
+ * @param {{ a?: { json?: string[] }}} [config]
+ */
+function f1({ a: { json = [] } = {} } = {}) { return json }
+>f1 : Symbol(f1, Decl(index.js, 29, 1))
+>json : Symbol(json, Decl(index.js, 36, 18))
+>json : Symbol(json, Decl(index.js, 36, 18))
+
+/**
+ * @param {[[string[]?]?]} [x]
+ */
+function f2([[json = []] = []] = []) { return json }
+>f2 : Symbol(f2, Decl(index.js, 36, 59))
+>json : Symbol(json, Decl(index.js, 41, 14))
+>json : Symbol(json, Decl(index.js, 41, 14))
+
diff --git a/tests/baselines/reference/destructuringParameterDeclaration9(strict=true).types b/tests/baselines/reference/destructuringParameterDeclaration9(strict=true).types
new file mode 100644
index 0000000000000..8b6f457266be6
--- /dev/null
+++ b/tests/baselines/reference/destructuringParameterDeclaration9(strict=true).types
@@ -0,0 +1,131 @@
+//// [tests/cases/conformance/es6/destructuring/destructuringParameterDeclaration9.ts] ////
+
+=== index.js ===
+/**
+ * @param {Object} [config]
+ * @param {Partial<Record<'json' | 'jsonc' | 'json5', string[]>>} [config.additionalFiles]
+ */
+export function prepareConfig({
+>prepareConfig : ({ additionalFiles: { json } }?: { additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>> | undefined; } | undefined) => void
+>              : ^                             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+
+    additionalFiles: {
+>additionalFiles : any
+>                : ^^^
+
+        json = []
+>json : string[]
+>     : ^^^^^^^^
+>[] : never[]
+>   : ^^^^^^^
+
+    } = {}
+>{} : {}
+>   : ^^
+
+} = {}) {
+>{} : {}
+>   : ^^
+
+    json // string[]
+>json : string[]
+>     : ^^^^^^^^
+}
+
+export function prepareConfigWithoutAnnotation({
+>prepareConfigWithoutAnnotation : ({ additionalFiles: { json } }?: { additionalFiles?: { json?: never[] | undefined; } | undefined; }) => void
+>                               : ^                             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+
+    additionalFiles: {
+>additionalFiles : any
+>                : ^^^
+
+        json = []
+>json : any[]
+>     : ^^^^^
+>[] : never[]
+>   : ^^^^^^^
+
+    } = {}
+>{} : {}
+>   : ^^
+
+} = {}) {
+>{} : {}
+>   : ^^
+
+    json
+>json : any[]
+>     : ^^^^^
+}
+
+/** @type {(param: {
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+}) => void} */
+export const prepareConfigWithContextualSignature = ({
+>prepareConfigWithContextualSignature : (param: { additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>; }) => void
+>                                     : ^     ^^                                                                            ^^^^^    
+>({    additionalFiles: {        json = []    } = {}} = {})=>  {    json // string[]} : ({ additionalFiles: { json } }?: { additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>; }) => void
+>                                                                                     : ^                             ^^^^^^^^^^^^^^^^^^^^^^^                                                     ^^^^^^^^    
+
+    additionalFiles: {
+>additionalFiles : any
+>                : ^^^
+
+        json = []
+>json : string[]
+>     : ^^^^^^^^
+>[] : never[]
+>   : ^^^^^^^
+
+    } = {}
+>{} : {}
+>   : ^^
+
+} = {})=>  {
+>{} : {}
+>   : ^^
+
+    json // string[]
+>json : string[]
+>     : ^^^^^^^^
+}
+
+// Additional repros from https://github.com/microsoft/TypeScript/issues/59936
+
+/**
+ * @param {{ a?: { json?: string[] }}} [config]
+ */
+function f1({ a: { json = [] } = {} } = {}) { return json }
+>f1 : ({ a: { json } }?: { a?: { json?: string[]; }; } | undefined) => string[]
+>   : ^               ^^^^^^^^^                    ^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+>a : any
+>  : ^^^
+>json : string[]
+>     : ^^^^^^^^
+>[] : never[]
+>   : ^^^^^^^
+>{} : {}
+>   : ^^
+>{} : {}
+>   : ^^
+>json : string[]
+>     : ^^^^^^^^
+
+/**
+ * @param {[[string[]?]?]} [x]
+ */
+function f2([[json = []] = []] = []) { return json }
+>f2 : ([[json]]?: [([(string[] | undefined)?] | undefined)?] | undefined) => string[]
+>   : ^        ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+>json : string[]
+>     : ^^^^^^^^
+>[] : never[]
+>   : ^^^^^^^
+>[] : []
+>   : ^^
+>[] : []
+>   : ^^
+>json : string[]
+>     : ^^^^^^^^
+
diff --git a/tests/cases/conformance/es6/destructuring/destructuringParameterDeclaration10.ts b/tests/cases/conformance/es6/destructuring/destructuringParameterDeclaration10.ts
new file mode 100644
index 0000000000000..997341c7cb1a6
--- /dev/null
+++ b/tests/cases/conformance/es6/destructuring/destructuringParameterDeclaration10.ts
@@ -0,0 +1,30 @@
+// @strict: true, false
+// @noEmit: true
+
+export function prepareConfig({
+    additionalFiles: {
+        json = []
+    } = {}
+}: {
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+} = {}) {
+    json // string[]
+}
+
+export function prepareConfigWithoutAnnotation({
+    additionalFiles: {
+        json = []
+    } = {}
+} = {}) {
+    json
+}
+
+export const prepareConfigWithContextualSignature: (param:{
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+}) => void = ({
+    additionalFiles: {
+        json = []
+    } = {}
+} = {}) => {
+    json // string[]
+}
diff --git a/tests/cases/conformance/es6/destructuring/destructuringParameterDeclaration9.ts b/tests/cases/conformance/es6/destructuring/destructuringParameterDeclaration9.ts
new file mode 100644
index 0000000000000..d033af2b0891e
--- /dev/null
+++ b/tests/cases/conformance/es6/destructuring/destructuringParameterDeclaration9.ts
@@ -0,0 +1,51 @@
+// @strict: true, false
+// @noEmit: true
+// @allowJs: true
+// @checkJs: true
+
+// https://github.com/microsoft/TypeScript/issues/59936
+
+// @filename: index.js
+
+/**
+ * @param {Object} [config]
+ * @param {Partial<Record<'json' | 'jsonc' | 'json5', string[]>>} [config.additionalFiles]
+ */
+export function prepareConfig({
+    additionalFiles: {
+        json = []
+    } = {}
+} = {}) {
+    json // string[]
+}
+
+export function prepareConfigWithoutAnnotation({
+    additionalFiles: {
+        json = []
+    } = {}
+} = {}) {
+    json
+}
+
+/** @type {(param: {
+  additionalFiles?: Partial<Record<"json" | "jsonc" | "json5", string[]>>;
+}) => void} */
+export const prepareConfigWithContextualSignature = ({
+    additionalFiles: {
+        json = []
+    } = {}
+} = {})=>  {
+    json // string[]
+}
+
+// Additional repros from https://github.com/microsoft/TypeScript/issues/59936
+
+/**
+ * @param {{ a?: { json?: string[] }}} [config]
+ */
+function f1({ a: { json = [] } = {} } = {}) { return json }
+
+/**
+ * @param {[[string[]?]?]} [x]
+ */
+function f2([[json = []] = []] = []) { return json }