diff --git a/.github/workflows/ci.yaml b/.github/workflows/ci.yaml
index dbcfc93cc8..298f91bddd 100644
--- a/.github/workflows/ci.yaml
+++ b/.github/workflows/ci.yaml
@@ -984,6 +984,19 @@ jobs:
       - run: pnpm playwright:install
         working-directory: site
 
+      # Cache the Coder release binaries downloaded by the outdatedCLI /
+      # outdatedAgent e2e tests so most runs skip the flaky GitHub release
+      # download entirely. The cache key is keyed off the test files that pin
+      # the downloaded versions, so it invalidates when those versions change.
+      - name: Restore e2e Coder release binary cache
+        id: coder-e2e-cache
+        uses: actions/cache/restore@55cc8345863c7cc4c66a329aec7e433d2d1c52a9 # v6.1.0
+        with:
+          path: /tmp/coder-e2e-cache
+          key: coder-e2e-cache-${{ runner.os }}-${{ hashFiles('site/e2e/tests/outdatedCLI.spec.ts', 'site/e2e/tests/outdatedAgent.spec.ts') }}
+          restore-keys: |
+            coder-e2e-cache-${{ runner.os }}-
+
       # Run tests that don't require a premium license without a premium license
       - run: pnpm playwright:test --forbid-only --workers 1
         if: ${{ !matrix.variant.premium }}
@@ -1000,6 +1013,16 @@ jobs:
           CODER_E2E_REQUIRE_PREMIUM_TESTS: "1"
         working-directory: site
 
+      - name: Save e2e Coder release binary cache
+        # Only the default branch is trusted to write the cache, so PR runs
+        # cannot poison the cache that subsequent runs restore from. Skip when
+        # the cache already had an exact key hit (no new content).
+        if: always() && github.ref == 'refs/heads/main' && steps.coder-e2e-cache.outputs.cache-hit != 'true'
+        uses: actions/cache/save@55cc8345863c7cc4c66a329aec7e433d2d1c52a9 # v6.1.0
+        with:
+          path: /tmp/coder-e2e-cache
+          key: ${{ steps.coder-e2e-cache.outputs.cache-primary-key }}
+
       - name: Upload Playwright failure artifacts
         if: failure() && github.actor != 'dependabot[bot]' && runner.os == 'Linux' && !github.event.pull_request.head.repo.fork
         uses: actions/upload-artifact@043fb46d1a93c77aae656e7c1c64a875d1fc6a0a # v7.0.1
diff --git a/site/e2e/helpers.ts b/site/e2e/helpers.ts
index 637951887f..9d58d98aff 100644
--- a/site/e2e/helpers.ts
+++ b/site/e2e/helpers.ts
@@ -487,38 +487,60 @@ export const downloadCoderVersion = async (
 		return binaryPath;
 	}
 
-	// Run our official install script to install the binary
-	await new Promise<void>((resolve, reject) => {
-		const cp = spawn(
-			path.join(__dirname, "../../install.sh"),
-			[
-				"--version",
-				versionNumber,
-				"--method",
-				"standalone",
-				"--prefix",
-				tempDir,
-				"--binary-name",
-				binaryName,
-			],
-			{
-				env: {
-					...process.env,
-					XDG_CACHE_HOME: "/tmp/coder-e2e-cache",
-					TRACE: "1", // tells install.sh to `set -x`, helpful if something goes wrong
+	// runInstallScript runs our official install script to install the binary,
+	// resolving with the script's exit code.
+	const runInstallScript = (): Promise<number> =>
+		new Promise<number>((resolve, reject) => {
+			const cp = spawn(
+				path.join(__dirname, "../../install.sh"),
+				[
+					"--version",
+					versionNumber,
+					"--method",
+					"standalone",
+					"--prefix",
+					tempDir,
+					"--binary-name",
+					binaryName,
+				],
+				{
+					env: {
+						...process.env,
+						XDG_CACHE_HOME: "/tmp/coder-e2e-cache",
+						TRACE: "1", // tells install.sh to `set -x`, helpful if something goes wrong
+					},
 				},
-			},
-		);
-		cp.stderr.on("data", (data) => console.error(data.toString()));
-		cp.stdout.on("data", (data) => console.info(data.toString()));
-		cp.on("close", (code) => {
-			if (code === 0) {
-				resolve();
-			} else {
-				reject(new Error(`install.sh failed with code ${code}`));
-			}
+			);
+			cp.stderr.on("data", (data) => console.error(data.toString()));
+			cp.stdout.on("data", (data) => console.info(data.toString()));
+			cp.on("error", (err) => reject(err));
+			cp.on("close", (code) => resolve(code ?? 1));
 		});
-	});
+
+	// The install script downloads the release asset from GitHub, which
+	// occasionally returns a transient error (e.g. HTTP 403/503, surfacing as a
+	// nonzero curl exit code). Retry with exponential backoff so a single hiccup
+	// does not fail the test. Partial downloads are resumed and completed
+	// binaries are reused across attempts by install.sh.
+	const maxAttempts = 5;
+	for (let attempt = 1; attempt <= maxAttempts; attempt++) {
+		const code = await runInstallScript();
+		if (code === 0) {
+			return binaryPath;
+		}
+		if (attempt === maxAttempts) {
+			throw new Error(
+				`install.sh failed with code ${code} after ${maxAttempts} attempts`,
+			);
+		}
+		// Exponential backoff with jitter: ~1s, 2s, 4s, 8s between attempts.
+		const backoffMs =
+			2 ** (attempt - 1) * 1000 + Math.floor(Math.random() * 1000);
+		console.error(
+			`install.sh attempt ${attempt}/${maxAttempts} failed with code ${code}; retrying in ${backoffMs}ms`,
+		);
+		await new Promise((resolve) => setTimeout(resolve, backoffMs));
+	}
 	return binaryPath;
 };