diff --git a/apps/server/src/workspace/WorkspaceEntries.test.ts b/apps/server/src/workspace/WorkspaceEntries.test.ts
index d861935fe17cc..154a260eea0f4 100644
--- a/apps/server/src/workspace/WorkspaceEntries.test.ts
+++ b/apps/server/src/workspace/WorkspaceEntries.test.ts
@@ -675,6 +675,29 @@ it.layer(layerTest, { excludeTestServices: true })("WorkspaceEntries", (it) => {
       }),
     );
 
+    it.effect("keeps matches past the truncated part of a long line", () =>
+      Effect.gen(function* () {
+        const cwd = yield* makeTempDir({ prefix: "t3code-workspace-content-long-line-" });
+        yield* writeTextFile(cwd, "dist/app.min.js", `${"x".repeat(600)} needleSuffix\n`);
+
+        const workspaceEntries = yield* WorkspaceEntries.WorkspaceEntries;
+        const search = (wholeWord: boolean) =>
+          workspaceEntries.searchContents({
+            cwd,
+            query: "needle",
+            limit: 100,
+            caseSensitive: true,
+            wholeWord,
+            useRegex: false,
+          });
+
+        expect((yield* search(false)).matches).toEqual([
+          expect.objectContaining({ path: "dist/app.min.js", lineNumber: 1 }),
+        ]);
+        expect((yield* search(true)).matches).toEqual([]);
+      }),
+    );
+
     it.effect("keeps answering from the live index when a refresh outlasts the scan wait", () =>
       Effect.gen(function* () {
         const cwd = yield* makeTempDir({ prefix: "t3code-workspace-content-refresh-" });
diff --git a/apps/server/src/workspace/WorkspaceSearchIndex.ts b/apps/server/src/workspace/WorkspaceSearchIndex.ts
index d5539e2f4e718..8b8782b200504 100644
--- a/apps/server/src/workspace/WorkspaceSearchIndex.ts
+++ b/apps/server/src/workspace/WorkspaceSearchIndex.ts
@@ -505,7 +505,8 @@ export const make = Effect.fn("WorkspaceSearchIndex.make")(function* (
         const matchRanges = mapContentMatchRanges(match.lineContent, match.matchRanges).filter(
           (range) => !input.wholeWord || isWholeWordRange(match.lineContent, range),
         );
-        if (matchRanges.length === 0) continue;
+        // fff reports hits past its 512-char lineContent cap with no ranges, so whole words can't be verified there.
+        if (input.wholeWord && matchRanges.length === 0) continue;
         matches.push({
           path: toPosixPath(match.relativePath),
           lineNumber: match.lineNumber,