diff --git a/e2e/fixtures.ts b/e2e/fixtures.ts
index ad191a6..9127743 100644
--- a/e2e/fixtures.ts
+++ b/e2e/fixtures.ts
@@ -12,41 +12,12 @@ import * as path from "path";
 export const test = base.extend<{ server: { baseURL: string }; page: Page }>({
   server: [
     async ({}, use) => {
-      const dbPath = path.join(
-        os.tmpdir(),
-        `sustenance-e2e-${process.pid}-${Date.now()}-${Math.random()
-          .toString(36)
-          .slice(2)}.db`,
-      );
-      const port = 3200 + Math.floor(Math.random() * 2000);
-      const baseURL = `http://127.0.0.1:${port}`;
-
-      const child = spawn(
-        path.resolve(__dirname, "..", "target", "debug", "sustenance"),
-        [],
-        {
-          env: {
-            ...process.env,
-            DATABASE_PATH: dbPath,
-            REGISTRATION_MODE: "open",
-            BIND_ADDRESS: `127.0.0.1:${port}`,
-            // Point SEED_CONFIG at a nonexistent file so no default user is created.
-            SEED_CONFIG: path.join(os.tmpdir(), "sustenance-e2e-no-seed.json"),
-          },
-          stdio: "ignore",
-          // Run in its own process group so we can kill the whole tree.
-          detached: true,
-        },
-      );
-
-      await waitForServer(baseURL, child);
-
-      await use({ baseURL });
-
-      await killTree(child);
+      const server = await startServer();
+      await use({ baseURL: server.baseURL });
+      await killTree(server.child);
       // Clean up the DB files (including -wal / -shm).
       for (const suffix of ["", "-wal", "-shm"]) {
-        fs.rmSync(dbPath + suffix, { force: true });
+        fs.rmSync(server.dbPath + suffix, { force: true });
       }
     },
     { scope: "test", auto: true },
@@ -61,6 +32,60 @@ export const test = base.extend<{ server: { baseURL: string }; page: Page }>({
   },
 });
 
+/** Starts a server, retrying on a fresh port if the first attempt fails to bind. */
+async function startServer() {
+  for (let attempt = 0; attempt < 5; attempt++) {
+    const dbPath = path.join(
+      os.tmpdir(),
+      `sustenance-e2e-${process.pid}-${Date.now()}-${Math.random()
+        .toString(36)
+        .slice(2)}.db`,
+    );
+    const port = 20000 + Math.floor(Math.random() * 30000);
+    const baseURL = `http://127.0.0.1:${port}`;
+
+    const child = spawn(
+      path.resolve(__dirname, "..", "target", "debug", "sustenance"),
+      [],
+      {
+        env: {
+          ...process.env,
+          DATABASE_PATH: dbPath,
+          REGISTRATION_MODE: "open",
+          BIND_ADDRESS: `127.0.0.1:${port}`,
+          // Point SEED_CONFIG at a nonexistent file so no default user is created.
+          SEED_CONFIG: path.join(os.tmpdir(), "sustenance-e2e-no-seed.json"),
+        },
+        stdio: ["ignore", "ignore", "pipe"],
+        // Run in its own process group so we can kill the whole tree.
+        detached: true,
+      },
+    );
+
+    let stderr = "";
+    child.stderr?.on("data", (chunk) => {
+      stderr += chunk.toString();
+    });
+
+    try {
+      await waitForServer(baseURL, child);
+      return { baseURL, child, dbPath };
+    } catch (error) {
+      // The server may have failed to bind (port collision). Clean up and retry.
+      await killTree(child);
+      for (const suffix of ["", "-wal", "-shm"]) {
+        fs.rmSync(dbPath + suffix, { force: true });
+      }
+      if (attempt === 4) {
+        throw new Error(
+          `server failed to start after retries; last stderr:\n${stderr}\n${error}`,
+        );
+      }
+    }
+  }
+  throw new Error("unreachable");
+}
+
 async function waitForServer(baseURL: string, child: ChildProcess) {
   const deadline = Date.now() + 60_000;
   while (Date.now() < deadline) {
diff --git a/e2e/playwright.config.ts b/e2e/playwright.config.ts
index eb71193..c5992d3 100644
--- a/e2e/playwright.config.ts
+++ b/e2e/playwright.config.ts
@@ -3,7 +3,7 @@ import { defineConfig } from "@playwright/test";
 export default defineConfig({
   testDir: "./tests",
   timeout: 30_000,
-  retries: 0,
+  retries: 2,
   use: {
     trace: "on-first-retry",
   },