diff --git a/src/__tests__/pdfRateLimit-coverage.test.ts b/src/__tests__/pdfRateLimit-coverage.test.ts
new file mode 100644
index 0000000..b074ac9
--- /dev/null
+++ b/src/__tests__/pdfRateLimit-coverage.test.ts
@@ -0,0 +1,155 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import { isProKey } from "../services/keys.js";
+
+// Tests to improve coverage for pdfRateLimit.ts
+// Target: per-key queue fairness rejection and cleanupExpiredEntries behavior
+
+const mockNext = vi.fn();
+const headers: Record<string, string> = {};
+const mockSet = vi.fn((k: string, v: string) => { headers[k] = v; });
+const mockJson = vi.fn();
+const mockStatus = vi.fn(() => ({ json: mockJson }));
+
+function makeReq(key = "test-key"): any {
+  return {
+    apiKeyInfo: { key, tier: "free", email: "t@t.com", createdAt: "2025-01-01" },
+    headers: {},
+  };
+}
+
+function makeRes(): any {
+  Object.keys(headers).forEach((k) => delete headers[k]);
+  mockSet.mockClear();
+  mockJson.mockClear();
+  mockStatus.mockClear();
+  return { set: mockSet, status: mockStatus, json: mockJson };
+}
+
+describe("pdfRateLimit middleware - additional coverage", () => {
+  let pdfRateLimitMiddleware: any;
+
+  beforeEach(async () => {
+    vi.clearAllMocks();
+    vi.resetModules();
+    const mod = await import("../middleware/pdfRateLimit.js");
+    pdfRateLimitMiddleware = mod.pdfRateLimitMiddleware;
+  });
+
+  it("should reject per-key queue fairness when MAX_QUEUED_PER_KEY (3) exceeded", async () => {
+    vi.mocked(isProKey).mockReturnValue(false);
+    
+    // Fill up 3 concurrent slots with different keys
+    const concurrentReqs = [];
+    for (let i = 0; i < 3; i++) {
+      const req = makeReq(`concurrent-${i}`);
+      const res = makeRes();
+      pdfRateLimitMiddleware(req, res, mockNext);
+      concurrentReqs.push(req);
+      await (req as any).acquirePdfSlot(); // Acquire but don't release
+    }
+
+    // Now try to queue 4 requests with the same key (should only allow 3 per key)
+    const sameKeyPromises = [];
+    const sameKey = "same-key";
+    
+    // Queue 3 requests with the same key (this should work)
+    for (let i = 0; i < 3; i++) {
+      const req = makeReq(sameKey);
+      const res = makeRes();
+      pdfRateLimitMiddleware(req, res, mockNext);
+      sameKeyPromises.push((req as any).acquirePdfSlot());
+    }
+
+    // Try to queue a 4th request with the same key - this should fail with QUEUE_FULL
+    const req4th = makeReq(sameKey);
+    const res4th = makeRes();
+    pdfRateLimitMiddleware(req4th, res4th, mockNext);
+    
+    await expect((req4th as any).acquirePdfSlot()).rejects.toThrow("QUEUE_FULL");
+  });
+
+  it("should call cleanupExpiredEntries and remove expired rate limit entries", async () => {
+    vi.mocked(isProKey).mockReturnValue(false);
+    vi.useFakeTimers();
+    
+    try {
+      // Create a rate limit entry
+      const req = makeReq("cleanup-test-key");
+      const res = makeRes();
+      pdfRateLimitMiddleware(req, res, mockNext);
+      
+      // Verify it was allowed (first request)
+      expect(mockNext).toHaveBeenCalled();
+      mockNext.mockClear();
+      
+      // Advance time past the rate limit window (60s + 1ms)
+      vi.advanceTimersByTime(60_001);
+      
+      // Make another request - this should trigger cleanup and reset the rate limit
+      const req2 = makeReq("cleanup-test-key");
+      const res2 = makeRes();
+      pdfRateLimitMiddleware(req2, res2, mockNext);
+      
+      // Should be allowed again since cleanup removed the expired entry
+      expect(mockNext).toHaveBeenCalled();
+      expect(mockSet).toHaveBeenCalledWith("X-RateLimit-Remaining", "9"); // Should be 9 (10-1)
+      
+    } finally {
+      vi.useRealTimers();
+    }
+  });
+
+  it("should test automatic cleanup interval calls cleanupExpiredEntries", async () => {
+    vi.useFakeTimers();
+    
+    try {
+      // Import the module to trigger the setInterval
+      const mod = await import("../middleware/pdfRateLimit.js");
+      pdfRateLimitMiddleware = mod.pdfRateLimitMiddleware;
+      
+      vi.mocked(isProKey).mockReturnValue(false);
+      
+      // Create some rate limit entries that will expire
+      const req1 = makeReq("auto-cleanup-1");
+      const res1 = makeRes();
+      pdfRateLimitMiddleware(req1, res1, mockNext);
+      
+      const req2 = makeReq("auto-cleanup-2");
+      const res2 = makeRes();
+      pdfRateLimitMiddleware(req2, res2, mockNext);
+      
+      // Advance past expiration
+      vi.advanceTimersByTime(70_000); // 70 seconds
+      
+      // Trigger the automatic cleanup by advancing the interval timer
+      vi.advanceTimersByTime(60_000); // Cleanup runs every 60s
+      
+      // Create a new request - should start fresh since old entries were cleaned up
+      const req3 = makeReq("auto-cleanup-1");
+      const res3 = makeRes();
+      pdfRateLimitMiddleware(req3, res3, mockNext);
+      
+      expect(mockNext).toHaveBeenCalled();
+      
+    } finally {
+      vi.useRealTimers();
+    }
+  });
+
+  it("should handle unknown api key in middleware", () => {
+    vi.mocked(isProKey).mockReturnValue(false);
+    
+    // Request without apiKeyInfo (should default to "unknown")
+    const req = {
+      apiKeyInfo: undefined,
+      headers: {},
+    };
+    const res = makeRes();
+    
+    pdfRateLimitMiddleware(req, res, mockNext);
+    
+    // Should still set headers and call next (using "unknown" as key)
+    expect(mockSet).toHaveBeenCalledWith("X-RateLimit-Limit", "10");
+    expect(mockNext).toHaveBeenCalled();
+  });
+});
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