diff --git a/packages/ai/src/prompts/analyze-resume-system.md b/packages/ai/src/prompts/analyze-resume-system.md
index 6aefedf93..6fcdbd795 100644
--- a/packages/ai/src/prompts/analyze-resume-system.md
+++ b/packages/ai/src/prompts/analyze-resume-system.md
@@ -47,6 +47,7 @@ Do not include markdown, comments, or additional keys.
 4. Never invent candidate achievements or facts.
 5. If data is missing, call it out explicitly in rationale/suggestions.
 6. Keep scorecard dimensions practical and common for resume review.
+7. Use the current date from the analysis context for chronology checks. Do not flag a date on or before that date as future-dated.
 
 ## Suggestions Requirements
 
diff --git a/packages/api/src/features/ai/service.test.ts b/packages/api/src/features/ai/service.test.ts
index 57f3ef703..5b6f580f0 100644
--- a/packages/api/src/features/ai/service.test.ts
+++ b/packages/api/src/features/ai/service.test.ts
@@ -1,4 +1,5 @@
 import type { UIMessage } from "ai";
+import type { ResumeData } from "@reactive-resume/schema/resume/data";
 import { afterEach, describe, expect, it, vi } from "vitest";
 import { convertToModelMessages, modelMessageSchema } from "ai";
 
@@ -10,6 +11,7 @@ vi.mock("@reactive-resume/env/server", () => ({ env: envMock }));
 
 afterEach(() => {
 	vi.unstubAllGlobals();
+	vi.useRealTimers();
 });
 
 function stubOpenAICompatibleResponse(response?: { content?: string; finishReason?: string }) {
@@ -67,7 +69,7 @@ function stubRejectedFetch(error: unknown) {
 	return fetchMock;
 }
 
-const { testConnection } = await import("./service");
+const { analyzeResume, testConnection } = await import("./service");
 
 describe("AI provider connection test", () => {
 	it("names the rejected key instead of reporting a transport failure", async () => {
@@ -168,6 +170,26 @@ describe("AI provider connection test", () => {
 	});
 });
 
+describe("AI resume analysis", () => {
+	it("gives the model the actual current date for chronology checks", async () => {
+		vi.useFakeTimers();
+		vi.setSystemTime(new Date("2026-08-18T12:00:00Z"));
+
+		const response = stubOpenAICompatibleResponse({
+			content: JSON.stringify({
+				overallScore: 80,
+				scorecard: [{ dimension: "Clarity", score: 80, rationale: "Clear." }],
+				suggestions: [],
+				strengths: ["Clear experience."],
+			}),
+		});
+
+		await analyzeResume({ ...testInput(), resumeData: {} as ResumeData });
+
+		expect(JSON.stringify(response.getRequestBody())).toContain("Current date: 2026-08-18");
+	});
+});
+
 describe("AI chat service", () => {
 	it("tests OpenAI-compatible providers without requiring structured output", async () => {
 		const openAiCompatible = stubOpenAICompatibleResponse();
diff --git a/packages/api/src/features/ai/service.ts b/packages/api/src/features/ai/service.ts
index 755e04532..803629b4c 100644
--- a/packages/api/src/features/ai/service.ts
+++ b/packages/api/src/features/ai/service.ts
@@ -509,8 +509,9 @@ type AnalyzeResumeInput = z.infer<typeof aiCredentialsSchema> & {
 	resumeData: ResumeData;
 };
 
-function buildAnalyzeResumeSystemPrompt(resumeData: ResumeData): string {
-	return `${analyzeResumeSystemPromptTemplate}\n\n## Resume Data\n\n${JSON.stringify(resumeData, null, 2)}`;
+function buildAnalyzeResumeSystemPrompt(resumeData: ResumeData, now = new Date()): string {
+	const currentDate = now.toISOString().slice(0, 10);
+	return `${analyzeResumeSystemPromptTemplate}\n\n## Analysis Context\n\nCurrent date: ${currentDate} (UTC). Treat dates on or before this date as not future-dated. Flag a date as future-dated only when it is after the current date.\n\n## Resume Data\n\n${JSON.stringify(resumeData, null, 2)}`;
 }
 
 /** Sends resume data to the AI provider and returns a structured analysis, parsing raw JSON from the response text. */