diff --git a/packages/typescript/src/options/validate.ts b/packages/typescript/src/options/validate.ts
index c772ac0c1..5cb6a4c38 100644
--- a/packages/typescript/src/options/validate.ts
+++ b/packages/typescript/src/options/validate.ts
@@ -65,6 +65,11 @@ export function validatePaths(
             `@rollup/plugin-typescript: Path of Typescript compiler option '${dirProperty}' must be located inside Rollup 'dir' option.`
           );
         }
+      } else if(dirProperty === 'outDir') {
+        const fromTsDirToRollup = relative(compilerOptions[dirProperty],outputDir);
+        if (fromTsDirToRollup.startsWith('..')) {
+            context.error(`@rollup/plugin-typescript: Path of Typescript compiler option '${dirProperty}' must be located inside the same directory as the Rollup 'file' option.`);
+        }
       } else {
         const fromTsDirToRollup = relative(outputDir, compilerOptions[dirProperty]!);
         if (fromTsDirToRollup.startsWith('..')) {