diff --git a/src/compile-options.spec.ts b/src/compile-options.spec.ts
index b7d3ff8b8..dec3acfc8 100644
--- a/src/compile-options.spec.ts
+++ b/src/compile-options.spec.ts
@@ -5,6 +5,13 @@ import { determineOutDir } from './compile-options'
 describe('determineOutDir', () => {
   const isWindows = os.platform() === 'win32'
   it.each([
+    // Relative input path with explicit ./
+    ['./examples/*', 'examples/hello/contract.algo.ts', 'out', 'examples/hello/out'],
+    ['./examples/*', 'examples/hello/nested/contract.algo.ts', 'out', 'examples/hello/out/nested'],
+    ['./examples/**', 'examples/hello/nested/contract.algo.ts', 'out', 'examples/hello/nested/out'],
+    ['./examples', 'examples/hello/contract.algo.ts', 'out', 'examples/out/hello'],
+    ['./examples/hello', 'examples/hello/contract.algo.ts', 'out', 'examples/hello/out'],
+    ['./examples/hello/contract.algo.ts', 'examples/hello/contract.algo.ts', 'out', 'examples/hello/out'],
     // Relative outDir
     ['examples/*', 'examples/hello/contract.algo.ts', 'out', 'examples/hello/out'],
     ['examples/*', 'examples/hello/nested/contract.algo.ts', 'out', 'examples/hello/out/nested'],
diff --git a/src/compile-options.ts b/src/compile-options.ts
index 9b36b417f..ee1aa1fb1 100644
--- a/src/compile-options.ts
+++ b/src/compile-options.ts
@@ -83,8 +83,12 @@ export const buildCompileOptions = ({
   }
 }
 
+function trimCurrentDir(path: string) {
+  return path.startsWith('./') ? path.slice(2) : path
+}
+
 function findMinimalMatch(inputPath: string, testPath: string): string {
-  const [matchedPath] = minimatch.match([testPath], inputPath)
+  const [matchedPath] = minimatch.match([trimCurrentDir(testPath)], trimCurrentDir(inputPath))
   if (matchedPath) {
     if (matchedPath.endsWith('.algo.ts')) {
       return upath.dirname(matchedPath)