diff --git a/packages/plugin-dts/src/utils.ts b/packages/plugin-dts/src/utils.ts
index 703e55c3c..c24b1d8d3 100644
--- a/packages/plugin-dts/src/utils.ts
+++ b/packages/plugin-dts/src/utils.ts
@@ -5,6 +5,7 @@ import path, {
   basename,
   dirname,
   extname,
+  isAbsolute,
   join,
   normalize,
   relative,
@@ -185,10 +186,15 @@ async function addExtension(
 
   let redirectPath = path;
 
+  // Only add extension if redirectPath is an absolute or relative path
+  if (!isAbsolute(redirectPath) && !redirectPath.startsWith('.')) {
+    return redirectPath;
+  }
+
   // If the import path refers to a directory, it most likely actually refers to a `index.*` file due to Node's module resolution
   if (await isDirectory(join(dirname(dtsFile), redirectPath))) {
     // This uses `/` instead of `path.join` here because `join` removes potential "./" prefixes
-    redirectPath = `${redirectPath}/index`;
+    redirectPath = `${redirectPath.replace(/\/+$/, '')}/index`;
   }
 
   return `${redirectPath}${extension}`;
@@ -277,9 +283,12 @@ export async function redirectDtsImports(
       let redirectImportPath = importPath;
 
       if (absoluteImportPath && redirect.path) {
-        const isOutsideRootdir = !normalize(absoluteImportPath).startsWith(
-          normalize(rootDir) + path.sep,
+        const relativeRootDir = path.relative(
+          normalize(rootDir),
+          normalize(absoluteImportPath),
         );
+        const isOutsideRootdir =
+          relativeRootDir.startsWith('..') || path.isAbsolute(relativeRootDir);
 
         if (isOutsideRootdir) {
           const relativePath = relative(dirname(dtsFile), absoluteImportPath);
diff --git a/tests/integration/redirect/dts.test.ts b/tests/integration/redirect/dts.test.ts
index 6450bc342..fe3d66d7c 100644
--- a/tests/integration/redirect/dts.test.ts
+++ b/tests/integration/redirect/dts.test.ts
@@ -7,9 +7,9 @@ let contents: Awaited<ReturnType<typeof buildAndGetResults>>['contents'];
 beforeAll(async () => {
   const fixturePath = path.resolve(__dirname, './dts');
   contents = (await buildAndGetResults({ fixturePath, type: 'dts' })).contents;
-});
+}, 15000);
 
-test('redirect.dts default', async () => {
+test('redirect.dts.path: true with redirect.dts.extension: false - default', async () => {
   expect(contents.esm0).toMatchInlineSnapshot(`
     {
       "<ROOT>/tests/integration/redirect/dts/dist/default/esm/foo/foo.d.ts": "import { logRequest } from '../logger';
@@ -21,9 +21,10 @@ test('redirect.dts default', async () => {
     ",
       "<ROOT>/tests/integration/redirect/dts/dist/default/esm/index.d.ts": "import { logRequest } from './logger';
     import { logger } from '../../../compile/rslog';
+    import type { Baz } from './';
     import type { LoggerOptions } from './types';
     import { defaultOptions } from './types.js';
-    export { logRequest, logger, type LoggerOptions, defaultOptions };
+    export { type Baz as self, logRequest, logger, type LoggerOptions, defaultOptions, };
     export type { Foo } from './types';
     export type { Bar } from './types';
     export * from './foo';
@@ -47,12 +48,15 @@ test('redirect.dts default', async () => {
     export interface Bar {
         bar: string;
     }
+    export interface Baz {
+        baz: string;
+    }
     ",
     }
   `);
 });
 
-test('redirect.dts.path false', async () => {
+test('redirect.dts.path: false with redirect.dts.extension: false', async () => {
   expect(contents.esm1).toMatchInlineSnapshot(`
     {
       "<ROOT>/tests/integration/redirect/dts/dist/path-false/esm/foo/foo.d.ts": "import { logRequest } from '@src/logger';
@@ -64,9 +68,10 @@ test('redirect.dts.path false', async () => {
     ",
       "<ROOT>/tests/integration/redirect/dts/dist/path-false/esm/index.d.ts": "import { logRequest } from '@src/logger';
     import { logger } from 'rslog';
+    import type { Baz } from 'self-entry';
     import type { LoggerOptions } from './types';
     import { defaultOptions } from './types.js';
-    export { logRequest, logger, type LoggerOptions, defaultOptions };
+    export { type Baz as self, logRequest, logger, type LoggerOptions, defaultOptions, };
     export type { Foo } from '@src/types';
     export type { Bar } from 'types';
     export * from './foo';
@@ -90,12 +95,15 @@ test('redirect.dts.path false', async () => {
     export interface Bar {
         bar: string;
     }
+    export interface Baz {
+        baz: string;
+    }
     ",
     }
   `);
 });
 
-test('redirect.dts.extension true', async () => {
+test('redirect.dts.path: true with redirect.dts.extension: true', async () => {
   expect(contents.esm2).toMatchInlineSnapshot(`
     {
       "<ROOT>/tests/integration/redirect/dts/dist/extension-true/esm/foo/foo.d.ts": "import { logRequest } from '../logger.js';
@@ -107,9 +115,10 @@ test('redirect.dts.extension true', async () => {
     ",
       "<ROOT>/tests/integration/redirect/dts/dist/extension-true/esm/index.d.ts": "import { logRequest } from './logger.js';
     import { logger } from '../../../compile/rslog';
+    import type { Baz } from './index.js';
     import type { LoggerOptions } from './types.js';
     import { defaultOptions } from './types.js';
-    export { logRequest, logger, type LoggerOptions, defaultOptions };
+    export { type Baz as self, logRequest, logger, type LoggerOptions, defaultOptions, };
     export type { Foo } from './types.js';
     export type { Bar } from './types.js';
     export * from './foo/index.js';
@@ -133,13 +142,63 @@ test('redirect.dts.extension true', async () => {
     export interface Bar {
         bar: string;
     }
+    export interface Baz {
+        baz: string;
+    }
     ",
     }
   `);
 });
 
-test('redirect.dts.extension true with dts.autoExtension true', async () => {
+test('redirect.dts.path: false with dts.redirect.extension: true', async () => {
   expect(contents.esm3).toMatchInlineSnapshot(`
+    {
+      "<ROOT>/tests/integration/redirect/dts/dist/path-false-extension-true/esm/foo/foo.d.ts": "import { logRequest } from '@src/logger';
+    import { logger } from 'rslog';
+    import { logRequest as logRequest2 } from '../logger.js';
+    export { logRequest, logRequest2, logger };
+    ",
+      "<ROOT>/tests/integration/redirect/dts/dist/path-false-extension-true/esm/foo/index.d.ts": "export type Barrel = string;
+    ",
+      "<ROOT>/tests/integration/redirect/dts/dist/path-false-extension-true/esm/index.d.ts": "import { logRequest } from '@src/logger';
+    import { logger } from 'rslog';
+    import type { Baz } from 'self-entry';
+    import type { LoggerOptions } from './types.js';
+    import { defaultOptions } from './types.js';
+    export { type Baz as self, logRequest, logger, type LoggerOptions, defaultOptions, };
+    export type { Foo } from '@src/types';
+    export type { Bar } from 'types';
+    export * from './foo/index.js';
+    export * from '@src/foo';
+    export * from './types.js';
+    export * from 'rslog';
+    export * from '@src/logger';
+    ",
+      "<ROOT>/tests/integration/redirect/dts/dist/path-false-extension-true/esm/logger.d.ts": "import type { Request } from 'express';
+    import type { LoggerOptions } from './types.js';
+    export declare function logRequest(req: Request, options: LoggerOptions): void;
+    ",
+      "<ROOT>/tests/integration/redirect/dts/dist/path-false-extension-true/esm/types.d.ts": "export interface LoggerOptions {
+        logLevel: 'info' | 'debug' | 'warn' | 'error';
+        logBody: boolean;
+    }
+    export declare const defaultOptions: LoggerOptions;
+    export interface Foo {
+        foo: string;
+    }
+    export interface Bar {
+        bar: string;
+    }
+    export interface Baz {
+        baz: string;
+    }
+    ",
+    }
+  `);
+});
+
+test('redirect.dts.extension: true with dts.autoExtension: true', async () => {
+  expect(contents.esm4).toMatchInlineSnapshot(`
     {
       "<ROOT>/tests/integration/redirect/dts/dist/auto-extension-true/foo/foo.d.mts": "import { logRequest } from '../logger.mjs';
     import { logger } from '../../../compile/rslog';
@@ -157,9 +216,10 @@ test('redirect.dts.extension true with dts.autoExtension true', async () => {
     ",
       "<ROOT>/tests/integration/redirect/dts/dist/auto-extension-true/index.d.mts": "import { logRequest } from './logger.mjs';
     import { logger } from '../../compile/rslog';
+    import type { Baz } from './index.mjs';
     import type { LoggerOptions } from './types.mjs';
     import { defaultOptions } from './types.mjs';
-    export { logRequest, logger, type LoggerOptions, defaultOptions };
+    export { type Baz as self, logRequest, logger, type LoggerOptions, defaultOptions, };
     export type { Foo } from './types.mjs';
     export type { Bar } from './types.mjs';
     export * from './foo/index.mjs';
@@ -170,9 +230,10 @@ test('redirect.dts.extension true with dts.autoExtension true', async () => {
     ",
       "<ROOT>/tests/integration/redirect/dts/dist/auto-extension-true/index.d.ts": "import { logRequest } from './logger.js';
     import { logger } from '../../compile/rslog';
+    import type { Baz } from './index.js';
     import type { LoggerOptions } from './types.js';
     import { defaultOptions } from './types.js';
-    export { logRequest, logger, type LoggerOptions, defaultOptions };
+    export { type Baz as self, logRequest, logger, type LoggerOptions, defaultOptions, };
     export type { Foo } from './types.js';
     export type { Bar } from './types.js';
     export * from './foo/index.js';
@@ -200,6 +261,9 @@ test('redirect.dts.extension true with dts.autoExtension true', async () => {
     export interface Bar {
         bar: string;
     }
+    export interface Baz {
+        baz: string;
+    }
     ",
       "<ROOT>/tests/integration/redirect/dts/dist/auto-extension-true/types.d.ts": "export interface LoggerOptions {
         logLevel: 'info' | 'debug' | 'warn' | 'error';
@@ -212,6 +276,9 @@ test('redirect.dts.extension true with dts.autoExtension true', async () => {
     export interface Bar {
         bar: string;
     }
+    export interface Baz {
+        baz: string;
+    }
     ",
     }
   `);
diff --git a/tests/integration/redirect/dts/rslib.config.ts b/tests/integration/redirect/dts/rslib.config.ts
index 80114ae48..6cf190290 100644
--- a/tests/integration/redirect/dts/rslib.config.ts
+++ b/tests/integration/redirect/dts/rslib.config.ts
@@ -3,7 +3,7 @@ import { generateBundleCjsConfig, generateBundleEsmConfig } from 'test-helper';
 
 export default defineConfig({
   lib: [
-    // 0 - default
+    // 0 - default - path: true extension: false
     generateBundleEsmConfig({
       dts: true,
       output: {
@@ -12,7 +12,7 @@ export default defineConfig({
         },
       },
     }),
-    // 1 - path: false
+    // 1 - path: false extension: false
     generateBundleEsmConfig({
       dts: true,
       output: {
@@ -26,7 +26,7 @@ export default defineConfig({
         },
       },
     }),
-    // 2 - extension: true
+    // 2 - path: true extension: true
     generateBundleEsmConfig({
       dts: true,
       output: {
@@ -40,7 +40,22 @@ export default defineConfig({
         },
       },
     }),
-    // 3 - extension: true with dts.autoExtension true
+    // 3 - path: false extension: true
+    generateBundleEsmConfig({
+      dts: true,
+      output: {
+        distPath: {
+          root: './dist/path-false-extension-true/esm',
+        },
+      },
+      redirect: {
+        dts: {
+          path: false,
+          extension: true,
+        },
+      },
+    }),
+    // 4 - extension: true with dts.autoExtension true
     generateBundleEsmConfig({
       dts: {
         autoExtension: true,
@@ -56,7 +71,7 @@ export default defineConfig({
         },
       },
     }),
-    // 4 - extension: true with dts.autoExtension true
+    // 5 - extension: true with dts.autoExtension true
     generateBundleCjsConfig({
       dts: {
         autoExtension: true,
diff --git a/tests/integration/redirect/dts/src/index.ts b/tests/integration/redirect/dts/src/index.ts
index b4402c115..ef376e58a 100644
--- a/tests/integration/redirect/dts/src/index.ts
+++ b/tests/integration/redirect/dts/src/index.ts
@@ -1,9 +1,16 @@
 import { logRequest } from '@src/logger';
 import { logger } from 'rslog';
+import type { Baz } from 'self-entry';
 import type { LoggerOptions } from './types';
 import { defaultOptions } from './types.js';
 
-export { logRequest, logger, type LoggerOptions, defaultOptions };
+export {
+  type Baz as self,
+  logRequest,
+  logger,
+  type LoggerOptions,
+  defaultOptions,
+};
 
 export type { Foo } from '@src/types';
 export type { Bar } from 'types';
diff --git a/tests/integration/redirect/dts/src/types.ts b/tests/integration/redirect/dts/src/types.ts
index cc9ccac52..ef6a9bf2b 100644
--- a/tests/integration/redirect/dts/src/types.ts
+++ b/tests/integration/redirect/dts/src/types.ts
@@ -15,3 +15,7 @@ export interface Foo {
 export interface Bar {
   bar: string;
 }
+
+export interface Baz {
+  baz: string;
+}
diff --git a/tests/integration/redirect/dts/tsconfig.json b/tests/integration/redirect/dts/tsconfig.json
index c86ca44d8..d70d332f2 100644
--- a/tests/integration/redirect/dts/tsconfig.json
+++ b/tests/integration/redirect/dts/tsconfig.json
@@ -5,7 +5,8 @@
     "paths": {
       "*": ["./src/*"],
       "@src/*": ["./src/*"],
-      "rslog": ["./compile/rslog"]
+      "rslog": ["./compile/rslog"],
+      "self-entry": ["./src"]
     }
   },
   "include": ["src/**/*"]