diff --git a/packages/typescript/src/options/validate.ts b/packages/typescript/src/options/validate.ts
index ae53834a3..c772ac0c1 100644
--- a/packages/typescript/src/options/validate.ts
+++ b/packages/typescript/src/options/validate.ts
@@ -66,7 +66,7 @@ export function validatePaths(
           );
         }
       } else {
-        const fromTsDirToRollup = relative(compilerOptions[dirProperty]!, outputDir);
+        const fromTsDirToRollup = relative(outputDir, compilerOptions[dirProperty]!);
         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.`