diff --git a/src/compiler/moduleSpecifiers.ts b/src/compiler/moduleSpecifiers.ts
index ac433ba8fed..5af3aab7d0f 100644
--- a/src/compiler/moduleSpecifiers.ts
+++ b/src/compiler/moduleSpecifiers.ts
@@ -613,7 +613,7 @@ function getLocalModuleSpecifier(moduleFileName: string, info: Info, compilerOpt
             prefersTsExtension(allowedEndings),
         );
 
-    const fromPaths = pathsOnly || fromPackageJsonImports === undefined ? paths && tryGetModuleNameFromPaths(relativeToBaseUrl, paths, allowedEndings, host, compilerOptions) : undefined;
+    const fromPaths = pathsOnly || fromPackageJsonImports === undefined ? paths && tryGetModuleNameFromPaths(relativeToBaseUrl, paths, allowedEndings, baseDirectory, getCanonicalFileName, host, compilerOptions) : undefined;
     if (pathsOnly) {
         return fromPaths;
     }
@@ -925,10 +925,11 @@ function tryGetModuleNameFromAmbientModule(moduleSymbol: Symbol, checker: TypeCh
     }
 }
 
-function tryGetModuleNameFromPaths(relativeToBaseUrl: string, paths: MapLike<readonly string[]>, allowedEndings: ModuleSpecifierEnding[], host: ModuleSpecifierResolutionHost, compilerOptions: CompilerOptions): string | undefined {
+function tryGetModuleNameFromPaths(relativeToBaseUrl: string, paths: MapLike<readonly string[]>, allowedEndings: ModuleSpecifierEnding[], baseDirectory: string, getCanonicalFileName: GetCanonicalFileName, host: ModuleSpecifierResolutionHost, compilerOptions: CompilerOptions): string | undefined {
     for (const key in paths) {
         for (const patternText of paths[key]) {
-            const pattern = normalizePath(patternText);
+            const normalized = normalizePath(patternText);
+            const pattern = getRelativePathIfInSameVolume(normalized, baseDirectory, getCanonicalFileName) ?? normalized;
             const indexOfStar = pattern.indexOf("*");
             // In module resolution, if `pattern` itself has an extension, a file with that extension is looked up directly,
             // meaning a '.ts' or '.d.ts' extension is allowed to resolve. This is distinct from the case where a '*' substitution
@@ -1290,6 +1291,8 @@ function tryGetModuleNameAsNodeModule({ path, isRedirect }: ModulePath, { getCan
                     subModuleName,
                     versionPaths.paths,
                     allowedEndings,
+                    packageRootPath,
+                    getCanonicalFileName,
                     host,
                     options,
                 );
diff --git a/tests/cases/fourslash/autoImportPathsConfigDir.ts b/tests/cases/fourslash/autoImportPathsConfigDir.ts
new file mode 100644
index 00000000000..0b451767b32
--- /dev/null
+++ b/tests/cases/fourslash/autoImportPathsConfigDir.ts
@@ -0,0 +1,18 @@
+/// <reference path="fourslash.ts" />
+
+// @Filename: tsconfig.json
+//// {
+////     "compilerOptions": {
+////         "paths": {
+////             "@root/*": ["${configDir}/src/*"]
+////         }
+////     }
+//// }
+
+// @Filename: src/one.ts
+//// export const one = 1;
+
+// @Filename: src/foo/two.ts
+//// one/**/
+
+verify.importFixModuleSpecifiers("", ["@root/one"]);