diff --git a/packages/handoff/src/index.ts b/packages/handoff/src/index.ts
index 30c912f227f5631949ee153740b478522430c0f0..1d0261f873bce9bb028e72f2c3393acf5ccfa2e9 100644
--- a/packages/handoff/src/index.ts
+++ b/packages/handoff/src/index.ts
@@ -174,10 +174,11 @@ function extractCandidateFiles(entries: SessionEntry[], conversationText: string
 		}
 	}
 
-	// Secondary: file-like patterns from conversation text
-	const filePattern = /(?:^|\s)([a-zA-Z0-9._\-/]+\.[a-zA-Z0-9]+)(?:\s|$|[,;:\)])/gm;
-	let match;
-	while ((match = filePattern.exec(conversationText)) !== null) {
+	// Secondary: file-like patterns from conversation text.
+	// Trailing lookahead so the boundary isn't consumed — otherwise adjacent
+	// files separated by a single space (e.g. "file1.txt file2.txt") get skipped.
+	const filePattern = /(?:^|\s)([a-zA-Z0-9._\-/]+\.[a-zA-Z0-9]+)(?=\s|$|[,;:)])/gm;
+	for (const match of conversationText.matchAll(filePattern)) {
 		const candidate = match[1];
 		if (candidate && !candidate.startsWith(".") && candidate.length > 2) {
 			files.add(candidate);