diff --git a/orchestrator/src/server/tailoring-flow.test.ts b/orchestrator/src/server/tailoring-flow.test.ts
new file mode 100644
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+++ b/orchestrator/src/server/tailoring-flow.test.ts
@@ -0,0 +1,85 @@
+
+import { describe, it, expect, vi, beforeEach } from 'vitest';
+import * as jobsRepo from './repositories/jobs.js';
+import * as pdfService from './services/pdf.js';
+import { generateFinalPdf } from './pipeline/orchestrator.js';
+
+// Mock dependencies
+vi.mock('./repositories/jobs.js');
+vi.mock('./services/pdf.js');
+
+describe('Tailoring Flow', () => {
+    beforeEach(() => {
+        vi.resetAllMocks();
+    });
+
+    it('should use manual overrides (tailoring) when generating PDF', async () => {
+        // 1. Setup: A job exists with manual tailoring applied (e.g. via the UI)
+        // This simulates a job where the user has edited the summary and projects
+        const tailoredJob = {
+            id: 'job-tailored-123',
+            jobDescription: 'Senior TypeScript Developer',
+            status: 'discovered',
+            // Manual overrides:
+            tailoredSummary: 'This is a manually edited summary specifically for this job.',
+            tailoredHeadline: 'Manually Edited Headline',
+            tailoredSkills: JSON.stringify(['React', 'TypeScript', 'Vitest']),
+            selectedProjectIds: 'project-a,project-c', // User selected specific projects
+        };
+
+        // Mock getting the job
+        vi.mocked(jobsRepo.getJobById).mockResolvedValue(tailoredJob as any);
+
+        // Mock successful PDF generation
+        vi.mocked(pdfService.generatePdf).mockResolvedValue({ success: true, pdfPath: 'generated/path/resume.pdf' });
+
+        // 2. Action: Trigger the PDF generation 
+        // (This would be called when the user clicks "Generate PDF")
+        const result = await generateFinalPdf('job-tailored-123');
+
+        // 3. Assertion: The operation was successful
+        expect(result.success).toBe(true);
+
+        // 4. Critical Assertion: The PDF service was called with the MANUALLY EDITED values
+        // This verifies that the user's edits are respected and not overwritten by AI defaults
+        expect(pdfService.generatePdf).toHaveBeenCalledTimes(1);
+        expect(pdfService.generatePdf).toHaveBeenCalledWith(
+            'job-tailored-123',
+            expect.objectContaining({
+                summary: 'This is a manually edited summary specifically for this job.',
+                headline: 'Manually Edited Headline',
+                skills: ['React', 'TypeScript', 'Vitest']
+            }),
+            'Senior TypeScript Developer', // Original JD
+            expect.any(String), // Profile path
+            'project-a,project-c' // The manually selected projects
+        );
+    });
+
+    it('should fall back to defaults if no tailoring is present', async () => {
+        // Setup: A job with no overrides
+        const rawJob = {
+            id: 'job-raw-456',
+            jobDescription: 'Junior Java Developer',
+            status: 'discovered',
+            // No tailored fields
+        };
+
+        vi.mocked(jobsRepo.getJobById).mockResolvedValue(rawJob as any);
+        vi.mocked(pdfService.generatePdf).mockResolvedValue({ success: true, pdfPath: 'path.pdf' });
+
+        await generateFinalPdf('job-raw-456');
+
+        expect(pdfService.generatePdf).toHaveBeenCalledWith(
+            'job-raw-456',
+            expect.objectContaining({
+                summary: '', // Empty if not tailored
+                headline: '',
+                skills: []
+            }),
+            'Junior Java Developer',
+            expect.any(String),
+            undefined // No projects selected
+        );
+    });
+});