diff --git a/src/hooks/grep-direct.ts b/src/hooks/grep-direct.ts
index 2c8bb52b..e0ffee31 100644
--- a/src/hooks/grep-direct.ts
+++ b/src/hooks/grep-direct.ts
@@ -294,9 +294,22 @@ export function parseBashGrep(cmd: string): GrepParams | null {
     ti++;
   }
 
-  const pattern = explicitPatterns.length > 0 ? explicitPatterns[0] : tokens[ti];
+  let pattern = explicitPatterns.length > 0 ? explicitPatterns[0] : tokens[ti];
   if (!pattern) return null;
 
+  // grep treats repeated -e/--regexp options as alternative patterns. Keep
+  // them together for the downstream line matcher, which accepts one regex.
+  // Fixed-string patterns must be escaped before building the alternation.
+  if (explicitPatterns.length > 1) {
+    const alternatives = explicitPatterns.map((p) =>
+      fixedString ? p.replace(/[.*+?^${}()|[\]\\]/g, "\\$&") : p,
+    );
+    // A bare alternation preserves grep's per-pattern OR semantics and keeps
+    // the alternatives visible to grep-core's SQL prefilter extractor.
+    pattern = alternatives.join("|");
+    fixedString = false;
+  }
+
   let target = explicitPatterns.length > 0 ? (tokens[ti] ?? "/") : (tokens[ti + 1] ?? "/");
   if (target === "." || target === "./") target = "/";
 
diff --git a/src/shell/grep-core.ts b/src/shell/grep-core.ts
index 02709ba9..76098b5e 100644
--- a/src/shell/grep-core.ts
+++ b/src/shell/grep-core.ts
@@ -614,11 +614,12 @@ export function extractRegexAlternationPrefilters(pattern: string): string[] | n
   if (escaped || !current) return null;
   parts.push(current);
 
-  const literals = [...new Set(
-    parts
-      .map((part) => extractRegexLiteralPrefilter(part))
-      .filter((part): part is string => typeof part === "string" && part.length >= 2),
-  )];
+  const branchLiterals = parts.map((part) => extractRegexLiteralPrefilter(part));
+  // An OR prefilter must retain at least one safe anchor from every branch.
+  // Dropping an unanchored branch would turn it into a false-negative filter.
+  if (branchLiterals.some((literal) => literal === null)) return null;
+
+  const literals = [...new Set(branchLiterals.filter((part): part is string => part !== null))];
   return literals.length > 0 ? literals : null;
 }
 
diff --git a/tests/claude-code/grep-core.test.ts b/tests/claude-code/grep-core.test.ts
index 995ad1b5..4ba77cd1 100644
--- a/tests/claude-code/grep-core.test.ts
+++ b/tests/claude-code/grep-core.test.ts
@@ -1010,6 +1010,10 @@ describe("regex literal prefilter", () => {
     expect(extractRegexAlternationPrefilters(".|.|.")).toBeNull();
   });
 
+  it("returns null when any branch has no safe literal anchor", () => {
+    expect(extractRegexAlternationPrefilters("apple|\\d+")).toBeNull();
+  });
+
   it("returns null when input has no alternation pipe", () => {
     expect(extractRegexAlternationPrefilters("foobar")).toBeNull();
   });
diff --git a/tests/claude-code/grep-direct.test.ts b/tests/claude-code/grep-direct.test.ts
index c4c2fa0b..2b4588a3 100644
--- a/tests/claude-code/grep-direct.test.ts
+++ b/tests/claude-code/grep-direct.test.ts
@@ -419,6 +419,33 @@ describe("parseBashGrep", () => {
   });
 });
 
+describe("parseBashGrep: repeated patterns", () => {
+  it("matches lines for every -e expression", async () => {
+    const parsed = parseBashGrep("grep -e apple -e banana /notes");
+    expect(parsed).not.toBeNull();
+    const api = {
+      query: vi.fn().mockResolvedValueOnce([{ path: "/notes/a.md", content: "apple pie\nbanana bread" }]),
+    } as any;
+    const result = await handleGrepDirect(api, "memory", "sessions", parsed!);
+    expect(result).toBe("apple pie\nbanana bread");
+    const sql = api.query.mock.calls[0][0] as string;
+    expect(sql).toContain("summary::text ILIKE '%apple%'");
+    expect(sql).toContain("summary::text ILIKE '%banana%'");
+    expect(sql).toContain("message::text ILIKE '%apple%'");
+    expect(sql).toContain("message::text ILIKE '%banana%'");
+  });
+
+  it("keeps repeated -F expressions literal", async () => {
+    const parsed = parseBashGrep("grep -F -e a.b -e banana /notes");
+    expect(parsed).not.toBeNull();
+    const api = {
+      query: vi.fn().mockResolvedValueOnce([{ path: "/notes/a.md", content: "a.b\naxb\nbanana" }]),
+    } as any;
+    const result = await handleGrepDirect(api, "memory", "sessions", parsed!);
+    expect(result).toBe("a.b\nbanana");
+  });
+});
+
 // ─── rg (ripgrep) ──────────────────────────────────────────────────────────
 //
 // Modern coding agents reach for `rg` by default for directory searches.