diff --git a/packages/eslint-plugin/__tests__/fixtures/test_src/feature1/slice1/inner2/sub/index.ts b/packages/eslint-plugin/__tests__/fixtures/test_src/feature1/slice1/inner2/sub/index.ts
new file mode 100644
index 00000000..e69de29b
diff --git a/packages/eslint-plugin/__tests__/shortestImport.test.ts b/packages/eslint-plugin/__tests__/shortestImport.test.ts
index c8908845..9d01554a 100644
--- a/packages/eslint-plugin/__tests__/shortestImport.test.ts
+++ b/packages/eslint-plugin/__tests__/shortestImport.test.ts
@@ -164,6 +164,10 @@ typescriptSetups.forEach((config) => {
           path: '../inner2',
           filename: './test_src/feature1/slice1/inner1/index.ts',
         },
+        {
+          path: '../../inner1/index',
+          filename: './test_src/feature1/slice1/inner2/sub/index.ts',
+        },
         {
           path: '~/feature1/slice2/second',
           filename: './test_src/feature1/slice1/inner1/index.ts',
diff --git a/packages/eslint-plugin/src/shortestImport.ts b/packages/eslint-plugin/src/shortestImport.ts
index 68fd0c38..7f3ccb1e 100644
--- a/packages/eslint-plugin/src/shortestImport.ts
+++ b/packages/eslint-plugin/src/shortestImport.ts
@@ -273,12 +273,14 @@ class RuleChecker {
     preferredAliasPaths: string[];
   }) {
     if (!aliasPaths.length && !baseUrlPaths.length) return relativePath;
+    const arePreferredAliasPathsInvalid =
+      preferredAliasPaths.length &&
+      [...aliasPaths, ...baseUrlPaths].some((aliasPath) =>
+        preferredAliasPaths.some((alias) => aliasPath.startsWith(alias)),
+      );
     const shouldAvoidRelative =
       this.relativeGoesThroughBaseUrl(relativePath, resolvedFilePath) ||
-      [...aliasPaths, ...baseUrlPaths].some((aliasPath) => {
-        if (!preferredAliasPaths.length) return false;
-        return preferredAliasPaths.some((alias) => aliasPath.startsWith(alias));
-      });
+      arePreferredAliasPathsInvalid;
     const allPathsWithLength = (aliasPaths.length ? aliasPaths : baseUrlPaths)
       .map((aliasPath) => {
         const parts = aliasPath.split('/');
@@ -319,7 +321,7 @@ class RuleChecker {
           if (part === '..') dotsOverPaths += 1;
           else dotsOverPaths -= 1;
         });
-        return dotsOverPaths > 0;
+        return dotsOverPaths >= 0;
       }
       return relativePathLength < shortestAliasPathLength;
     }