diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 8556832569b76..1e100505ec7e4 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -3561,6 +3561,12 @@ namespace ts {
                     (isLiteralImportTypeNode(location) ? location : undefined)?.argument.literal;
             const mode = contextSpecifier && isStringLiteralLike(contextSpecifier) ? getModeForUsageLocation(currentSourceFile, contextSpecifier) : currentSourceFile.impliedNodeFormat;
             const resolvedModule = getResolvedModule(currentSourceFile, moduleReference, mode);
+            if (resolvedModule?.extension === Extension.Json) {
+                const mod = findMatchingPatternAmbientModule(moduleReference);
+                if (mod) {
+                    return mod;
+                }
+            }
             const resolutionDiagnostic = resolvedModule && getResolutionDiagnostic(compilerOptions, resolvedModule);
             const sourceFile = resolvedModule
                 && (!resolutionDiagnostic || resolutionDiagnostic === Diagnostics.Module_0_was_resolved_to_1_but_jsx_is_not_set)
@@ -3594,18 +3600,11 @@ namespace ts {
                 return undefined;
             }
 
-            if (patternAmbientModules) {
-                const pattern = findBestPatternMatch(patternAmbientModules, _ => _.pattern, moduleReference);
-                if (pattern) {
-                    // If the module reference matched a pattern ambient module ('*.foo') but there's also a
-                    // module augmentation by the specific name requested ('a.foo'), we store the merged symbol
-                    // by the augmentation name ('a.foo'), because asking for *.foo should not give you exports
-                    // from a.foo.
-                    const augmentation = patternAmbientModuleAugmentations && patternAmbientModuleAugmentations.get(moduleReference);
-                    if (augmentation) {
-                        return getMergedSymbol(augmentation);
-                    }
-                    return getMergedSymbol(pattern.symbol);
+            // JSON files have been tried before, no need to try again.
+            if (resolvedModule?.extension !== Extension.Json) {
+                const mod = findMatchingPatternAmbientModule(moduleReference);
+                if (mod) {
+                    return mod;
                 }
             }
 
@@ -3680,6 +3679,26 @@ namespace ts {
             return undefined;
         }
 
+        function findMatchingPatternAmbientModule(moduleReference: string): Symbol | undefined {
+            if (!patternAmbientModules) {
+                return;
+            }
+            const pattern = findBestPatternMatch(patternAmbientModules, _ => _.pattern, moduleReference);
+            if (!pattern) {
+                return;
+            }
+            // If the module reference matched a pattern ambient module ('*.foo') but there's also a
+            // module augmentation by the specific name requested ('a.foo'), we store the merged symbol
+            // by the augmentation name ('a.foo'), because asking for *.foo should not give you exports
+            // from a.foo.
+            const augmentation = patternAmbientModuleAugmentations && patternAmbientModuleAugmentations.get(moduleReference);
+            if (augmentation) {
+                return getMergedSymbol(augmentation);
+            }
+            return getMergedSymbol(pattern.symbol);
+        }
+
+
         function errorOnImplicitAnyModule(isError: boolean, errorNode: Node, { packageId, resolvedFileName }: ResolvedModuleFull, moduleReference: string): void {
             const errorInfo = !isExternalModuleNameRelative(moduleReference) && packageId
                 ? typesPackageExists(packageId.name)
diff --git a/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite.js b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite.js
new file mode 100644
index 0000000000000..dd1a3bf8a6694
--- /dev/null
+++ b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite.js
@@ -0,0 +1,26 @@
+//// [tests/cases/compiler/moduleResolutionWithExtensions_jsonOverwrite.ts] ////
+
+//// [hello.locstring.json]
+{ "hello": "Hello World" }
+
+//// [types.d.ts]
+type ResourceId = string & { __ResourceId: void };
+declare module "*.locstring.json" {
+    const value: { [key: string]: ResourceId };
+    export default value;
+}
+
+//// [a.ts]
+import strings from './hello.locstring.json';
+
+strings.hello;
+
+
+//// [a.js]
+"use strict";
+var __importDefault = (this && this.__importDefault) || function (mod) {
+    return (mod && mod.__esModule) ? mod : { "default": mod };
+};
+exports.__esModule = true;
+var hello_locstring_json_1 = __importDefault(require("./hello.locstring.json"));
+hello_locstring_json_1["default"].hello;
diff --git a/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite.symbols b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite.symbols
new file mode 100644
index 0000000000000..8343eb5ed7979
--- /dev/null
+++ b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite.symbols
@@ -0,0 +1,28 @@
+=== /hello.locstring.json ===
+{ "hello": "Hello World" }
+>"hello" : Symbol("hello", Decl(hello.locstring.json, 0, 1))
+
+=== /types.d.ts ===
+type ResourceId = string & { __ResourceId: void };
+>ResourceId : Symbol(ResourceId, Decl(types.d.ts, 0, 0))
+>__ResourceId : Symbol(__ResourceId, Decl(types.d.ts, 0, 28))
+
+declare module "*.locstring.json" {
+>"*.locstring.json" : Symbol("*.locstring.json", Decl(types.d.ts, 0, 50))
+
+    const value: { [key: string]: ResourceId };
+>value : Symbol(value, Decl(types.d.ts, 2, 9))
+>key : Symbol(key, Decl(types.d.ts, 2, 20))
+>ResourceId : Symbol(ResourceId, Decl(types.d.ts, 0, 0))
+
+    export default value;
+>value : Symbol(value, Decl(types.d.ts, 2, 9))
+}
+
+=== /a.ts ===
+import strings from './hello.locstring.json';
+>strings : Symbol(strings, Decl(a.ts, 0, 6))
+
+strings.hello;
+>strings : Symbol(strings, Decl(a.ts, 0, 6))
+
diff --git a/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite.trace.json b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite.trace.json
new file mode 100644
index 0000000000000..56eae81f3ab28
--- /dev/null
+++ b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite.trace.json
@@ -0,0 +1,17 @@
+[
+    "======== Resolving module './hello.locstring.json' from '/a.ts'. ========",
+    "Module resolution kind is not specified, using 'NodeJs'.",
+    "Loading module as file / folder, candidate module location '/hello.locstring.json', target file type 'TypeScript'.",
+    "File '/hello.locstring.json.ts' does not exist.",
+    "File '/hello.locstring.json.tsx' does not exist.",
+    "File '/hello.locstring.json.d.ts' does not exist.",
+    "File name '/hello.locstring.json' has a '.json' extension - stripping it.",
+    "File '/hello.locstring.json.d.ts' does not exist.",
+    "Directory '/hello.locstring.json' does not exist, skipping all lookups in it.",
+    "Loading module as file / folder, candidate module location '/hello.locstring.json', target file type 'JavaScript'.",
+    "File '/hello.locstring.json.js' does not exist.",
+    "File '/hello.locstring.json.jsx' does not exist.",
+    "File name '/hello.locstring.json' has a '.json' extension - stripping it.",
+    "File '/hello.locstring.json' exist - use it as a name resolution result.",
+    "======== Module name './hello.locstring.json' was successfully resolved to '/hello.locstring.json'. ========"
+]
\ No newline at end of file
diff --git a/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite.types b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite.types
new file mode 100644
index 0000000000000..0c3c5d9a144ca
--- /dev/null
+++ b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite.types
@@ -0,0 +1,31 @@
+=== /hello.locstring.json ===
+{ "hello": "Hello World" }
+>{ "hello": "Hello World" } : { hello: string; }
+>"hello" : string
+>"Hello World" : "Hello World"
+
+=== /types.d.ts ===
+type ResourceId = string & { __ResourceId: void };
+>ResourceId : string & { __ResourceId: void; }
+>__ResourceId : void
+
+declare module "*.locstring.json" {
+>"*.locstring.json" : typeof import("*.locstring.json")
+
+    const value: { [key: string]: ResourceId };
+>value : { [key: string]: ResourceId; }
+>key : string
+
+    export default value;
+>value : { [key: string]: ResourceId; }
+}
+
+=== /a.ts ===
+import strings from './hello.locstring.json';
+>strings : { [key: string]: ResourceId; }
+
+strings.hello;
+>strings.hello : ResourceId
+>strings : { [key: string]: ResourceId; }
+>hello : ResourceId
+
diff --git a/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite2.js b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite2.js
new file mode 100644
index 0000000000000..13e9053d536cd
--- /dev/null
+++ b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite2.js
@@ -0,0 +1,32 @@
+//// [tests/cases/compiler/moduleResolutionWithExtensions_jsonOverwrite2.ts] ////
+
+//// [hello.locstring.json]
+{ "hello": "Hello World" }
+
+//// [hello.locstring.json.d.ts]
+declare const _default: {
+    hello: number;
+};
+export default _default;
+
+//// [types.d.ts]
+type ResourceId = string & { __ResourceId: void };
+declare module "*.locstring.json" {
+    const value: { [key: string]: ResourceId };
+    export default value;
+}
+
+//// [a.ts]
+import strings from './hello.locstring.json';
+
+strings.hello;
+
+
+//// [a.js]
+"use strict";
+var __importDefault = (this && this.__importDefault) || function (mod) {
+    return (mod && mod.__esModule) ? mod : { "default": mod };
+};
+exports.__esModule = true;
+var hello_locstring_json_1 = __importDefault(require("./hello.locstring.json"));
+hello_locstring_json_1["default"].hello;
diff --git a/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite2.symbols b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite2.symbols
new file mode 100644
index 0000000000000..0f069e397da8a
--- /dev/null
+++ b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite2.symbols
@@ -0,0 +1,37 @@
+=== /hello.locstring.json.d.ts ===
+declare const _default: {
+>_default : Symbol(_default, Decl(hello.locstring.json.d.ts, 0, 13))
+
+    hello: number;
+>hello : Symbol(hello, Decl(hello.locstring.json.d.ts, 0, 25))
+
+};
+export default _default;
+>_default : Symbol(_default, Decl(hello.locstring.json.d.ts, 0, 13))
+
+=== /types.d.ts ===
+type ResourceId = string & { __ResourceId: void };
+>ResourceId : Symbol(ResourceId, Decl(types.d.ts, 0, 0))
+>__ResourceId : Symbol(__ResourceId, Decl(types.d.ts, 0, 28))
+
+declare module "*.locstring.json" {
+>"*.locstring.json" : Symbol("*.locstring.json", Decl(types.d.ts, 0, 50))
+
+    const value: { [key: string]: ResourceId };
+>value : Symbol(value, Decl(types.d.ts, 2, 9))
+>key : Symbol(key, Decl(types.d.ts, 2, 20))
+>ResourceId : Symbol(ResourceId, Decl(types.d.ts, 0, 0))
+
+    export default value;
+>value : Symbol(value, Decl(types.d.ts, 2, 9))
+}
+
+=== /a.ts ===
+import strings from './hello.locstring.json';
+>strings : Symbol(strings, Decl(a.ts, 0, 6))
+
+strings.hello;
+>strings.hello : Symbol(hello, Decl(hello.locstring.json.d.ts, 0, 25))
+>strings : Symbol(strings, Decl(a.ts, 0, 6))
+>hello : Symbol(hello, Decl(hello.locstring.json.d.ts, 0, 25))
+
diff --git a/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite2.trace.json b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite2.trace.json
new file mode 100644
index 0000000000000..6a9da9b9c03b3
--- /dev/null
+++ b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite2.trace.json
@@ -0,0 +1,9 @@
+[
+    "======== Resolving module './hello.locstring.json' from '/a.ts'. ========",
+    "Module resolution kind is not specified, using 'NodeJs'.",
+    "Loading module as file / folder, candidate module location '/hello.locstring.json', target file type 'TypeScript'.",
+    "File '/hello.locstring.json.ts' does not exist.",
+    "File '/hello.locstring.json.tsx' does not exist.",
+    "File '/hello.locstring.json.d.ts' exist - use it as a name resolution result.",
+    "======== Module name './hello.locstring.json' was successfully resolved to '/hello.locstring.json.d.ts'. ========"
+]
\ No newline at end of file
diff --git a/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite2.types b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite2.types
new file mode 100644
index 0000000000000..c44c0925e06ce
--- /dev/null
+++ b/tests/baselines/reference/moduleResolutionWithExtensions_jsonOverwrite2.types
@@ -0,0 +1,36 @@
+=== /hello.locstring.json.d.ts ===
+declare const _default: {
+>_default : { hello: number; }
+
+    hello: number;
+>hello : number
+
+};
+export default _default;
+>_default : { hello: number; }
+
+=== /types.d.ts ===
+type ResourceId = string & { __ResourceId: void };
+>ResourceId : string & { __ResourceId: void; }
+>__ResourceId : void
+
+declare module "*.locstring.json" {
+>"*.locstring.json" : typeof import("*.locstring.json")
+
+    const value: { [key: string]: ResourceId };
+>value : { [key: string]: ResourceId; }
+>key : string
+
+    export default value;
+>value : { [key: string]: ResourceId; }
+}
+
+=== /a.ts ===
+import strings from './hello.locstring.json';
+>strings : { hello: number; }
+
+strings.hello;
+>strings.hello : number
+>strings : { hello: number; }
+>hello : number
+
diff --git a/tests/cases/compiler/moduleResolutionWithExtensions_jsonOverwrite.ts b/tests/cases/compiler/moduleResolutionWithExtensions_jsonOverwrite.ts
new file mode 100644
index 0000000000000..e3c64f16c8947
--- /dev/null
+++ b/tests/cases/compiler/moduleResolutionWithExtensions_jsonOverwrite.ts
@@ -0,0 +1,19 @@
+// @resolveJsonModule: true
+// @traceResolution: true
+// @esModuleInterop: true
+
+
+// @Filename: /hello.locstring.json
+{ "hello": "Hello World" }
+
+// @Filename: /types.d.ts
+type ResourceId = string & { __ResourceId: void };
+declare module "*.locstring.json" {
+    const value: { [key: string]: ResourceId };
+    export default value;
+}
+
+// @Filename: /a.ts
+import strings from './hello.locstring.json';
+
+strings.hello;
diff --git a/tests/cases/compiler/moduleResolutionWithExtensions_jsonOverwrite2.ts b/tests/cases/compiler/moduleResolutionWithExtensions_jsonOverwrite2.ts
new file mode 100644
index 0000000000000..13a82175bf5dd
--- /dev/null
+++ b/tests/cases/compiler/moduleResolutionWithExtensions_jsonOverwrite2.ts
@@ -0,0 +1,25 @@
+// @resolveJsonModule: true
+// @traceResolution: true
+// @esModuleInterop: true
+
+
+// @Filename: /hello.locstring.json
+{ "hello": "Hello World" }
+
+// @Filename: /hello.locstring.json.d.ts
+declare const _default: {
+    hello: number;
+};
+export default _default;
+
+// @Filename: /types.d.ts
+type ResourceId = string & { __ResourceId: void };
+declare module "*.locstring.json" {
+    const value: { [key: string]: ResourceId };
+    export default value;
+}
+
+// @Filename: /a.ts
+import strings from './hello.locstring.json';
+
+strings.hello;