diff --git a/src/server/routes/file-etag.ts b/src/server/routes/file-etag.ts
new file mode 100644
index 0000000..90ad240
--- /dev/null
+++ b/src/server/routes/file-etag.ts
@@ -0,0 +1,16 @@
+import { createHash } from "crypto";
+
+// Build an ETag that fingerprints both the upstream content (?v=<sha>) and
+// the anonymization config the user has saved. Without the config part, the
+// browser kept serving content anonymized under an older term list — see
+// #439 (anonymization "doesn't work" in regular tabs but works in incognito).
+export function fileETag(
+  versionParam: string | undefined,
+  options: unknown
+): string {
+  const h = createHash("sha1");
+  h.update(versionParam || "");
+  h.update("|");
+  h.update(JSON.stringify(options ?? null));
+  return `"f-${h.digest("hex")}"`;
+}
diff --git a/src/server/routes/file.ts b/src/server/routes/file.ts
index b20fbac..69157d4 100644
--- a/src/server/routes/file.ts
+++ b/src/server/routes/file.ts
@@ -2,6 +2,7 @@ import * as express from "express";
 import AnonymizedFile from "../../core/AnonymizedFile";
 import AnonymousError from "../../core/AnonymousError";
 import { getRepo, handleError } from "./route-utils";
+import { fileETag } from "./file-etag";
 
 export const router = express.Router();
 
@@ -51,12 +52,18 @@ router.get(
           anonymizedPath.substring(anonymizedPath.lastIndexOf("/") + 1)
         );
       }
-      if (req.query.v) {
-        // cache the file for a month
-        res.header("Cache-Control", "max-age=18144000");
-      } else {
-        // cache the file for 5min
-        res.header("Cache-Control", "max-age=300");
+      const etag = fileETag(
+        req.query.v as string | undefined,
+        repo.model.options
+      );
+      res.header("ETag", etag);
+      // Force the browser to revalidate every time. The previous 210-day
+      // max-age was keyed only on the upstream sha, so editing the
+      // anonymization term list left old anonymizations cached under the
+      // same URL.
+      res.header("Cache-Control", "private, no-cache, must-revalidate");
+      if (req.headers["if-none-match"] === etag) {
+        return res.status(304).end();
       }
       await f.send(res);
       await repo.countView();
diff --git a/test/file-etag.test.js b/test/file-etag.test.js
new file mode 100644
index 0000000..ecd78f8
--- /dev/null
+++ b/test/file-etag.test.js
@@ -0,0 +1,39 @@
+const { expect } = require("chai");
+require("ts-node/register/transpile-only");
+const { fileETag } = require("../src/server/routes/file-etag");
+
+describe("fileETag", function () {
+  it("changes when the upstream sha changes", function () {
+    const opts = { terms: ["alice"] };
+    expect(fileETag("sha1", opts)).to.not.equal(fileETag("sha2", opts));
+  });
+
+  // #439 — without folding the anonymization options into the ETag, editing
+  // the term list left the same URL serving stale anonymized bytes.
+  it("changes when the anonymization terms change", function () {
+    const a = fileETag("sha1", { terms: ["alice"] });
+    const b = fileETag("sha1", { terms: ["alice", "bob"] });
+    expect(a).to.not.equal(b);
+  });
+
+  it("changes when an anonymization toggle changes", function () {
+    const a = fileETag("sha1", { terms: ["alice"], image: true });
+    const b = fileETag("sha1", { terms: ["alice"], image: false });
+    expect(a).to.not.equal(b);
+  });
+
+  it("is stable for the same inputs", function () {
+    const opts = { terms: ["alice", "bob"], image: true };
+    expect(fileETag("sha1", opts)).to.equal(fileETag("sha1", opts));
+  });
+
+  it("treats missing version like an empty string", function () {
+    const opts = { terms: [] };
+    expect(fileETag(undefined, opts)).to.equal(fileETag("", opts));
+  });
+
+  it("returns a quoted opaque tag", function () {
+    const tag = fileETag("sha1", { terms: [] });
+    expect(tag).to.match(/^"f-[0-9a-f]{40}"$/);
+  });
+});