diff --git a/.github/workflows/e2e.yml b/.github/workflows/e2e.yml
index 3f79ea788ecf..a43e5d51226a 100644
--- a/.github/workflows/e2e.yml
+++ b/.github/workflows/e2e.yml
@@ -59,7 +59,7 @@ jobs:
         run: npm ci
 
       - name: Run builds
-        run: npm run -w wrangler build
+        run: npm run build
         env:
           NODE_ENV: "production"
 
diff --git a/packages/wrangler/e2e/c3-integration.test.ts b/packages/wrangler/e2e/c3-integration.test.ts
index f1d61294494f..7bb5db63f4fc 100644
--- a/packages/wrangler/e2e/c3-integration.test.ts
+++ b/packages/wrangler/e2e/c3-integration.test.ts
@@ -19,14 +19,16 @@ describe("c3 integration", () => {
 	let workerName: string;
 	let workerPath: string;
 	let workersDev: string | null = null;
-	let run: typeof shellac;
+	let runInRoot: typeof shellac;
+	let runInWorker: typeof shellac;
 	let normalize: (str: string) => string;
 
 	beforeAll(async () => {
 		const root = await makeRoot();
-		run = shellac.in(root).env(process.env);
+		runInRoot = shellac.in(root).env(process.env);
 		workerName = `smoke-test-worker-${crypto.randomBytes(4).toString("hex")}`;
 		workerPath = path.join(root, workerName);
+		runInWorker = shellac.in(workerPath).env(process.env);
 		normalize = (str) =>
 			normalizeOutput(str, { [workerName]: "smoke-test-worker" });
 	});
@@ -36,15 +38,19 @@ describe("c3 integration", () => {
 		const env = {
 			...process.env,
 			WRANGLER_C3_COMMAND: `exec ${pathToC3}`,
+			GIT_AUTHOR_NAME: "test-user",
+			GIT_AUTHOR_EMAIL: "test-user@cloudflare.com",
+			GIT_COMMITTER_NAME: "test-user",
+			GIT_COMMITTER_EMAIL: "test-user@cloudflare.com",
 		};
 
-		await run.env(env)`$$ ${WRANGLER} init ${workerName} --yes`;
+		await runInRoot.env(env)`$ ${WRANGLER} init ${workerName} --yes`;
 
 		expect(existsSync(workerPath)).toBe(true);
 	});
 
 	it("deploy the worker", async () => {
-		const { stdout, stderr } = await run.in(workerPath)`$ ${WRANGLER} deploy`;
+		const { stdout, stderr } = await runInWorker`$ ${WRANGLER} deploy`;
 		expect(normalize(stdout)).toMatchInlineSnapshot(`
 			"Total Upload: xx KiB / gzip: xx KiB
 			Uploaded smoke-test-worker (TIMINGS)
@@ -54,22 +60,30 @@ describe("c3 integration", () => {
 		`);
 		expect(stderr).toMatchInlineSnapshot('""');
 		workersDev = matchWorkersDev(stdout);
-		const responseText = await retry("", () =>
-			fetch(`https://${workerName}.${workersDev}`).then((r) => r.text())
+		const { text } = await retry(
+			(s) => s.status !== 200,
+			async () => {
+				const r = await fetch(`https://${workerName}.${workersDev}`);
+				return { text: await r.text(), status: r.status };
+			}
 		);
-		expect(responseText).toMatchInlineSnapshot('"Hello World!"');
+		expect(text).toMatchInlineSnapshot('"Hello World!"');
 	});
 
-	it("deletes the worker", async () => {
-		const { stdout, stderr } = await run.in(workerPath)`$ ${WRANGLER} delete`;
+	it("delete the worker", async () => {
+		const { stdout, stderr } = await runInWorker`$$ ${WRANGLER} delete`;
 		expect(normalize(stdout)).toMatchInlineSnapshot(`
 			"? Are you sure you want to delete smoke-test-worker? This action cannot be undone.
 			🤖 Using default value in non-interactive context: yes
 			Successfully deleted smoke-test-worker"
 		`);
 		expect(stderr).toMatchInlineSnapshot('""');
-		const status = await retry(200, () =>
-			fetch(`https://${workerName}.${workersDev}`).then((r) => r.status)
+		const { status } = await retry(
+			(s) => s.status === 200 || s.status === 500,
+			async () => {
+				const r = await fetch(`https://${workerName}.${workersDev}`);
+				return { text: await r.text(), status: r.status };
+			}
 		);
 		expect(status).toBe(404);
 	});
diff --git a/packages/wrangler/e2e/deploy.test.ts b/packages/wrangler/e2e/deploy.test.ts
index 17c29e80a907..78d9ccc4dd41 100644
--- a/packages/wrangler/e2e/deploy.test.ts
+++ b/packages/wrangler/e2e/deploy.test.ts
@@ -68,10 +68,14 @@ describe("deploy", () => {
 		expect(stderr).toMatchInlineSnapshot('""');
 		workersDev = matchWorkersDev(stdout);
 
-		const responseText = await retry("", () =>
-			fetch(`https://${workerName}.${workersDev}`).then((r) => r.text())
+		const { text } = await retry(
+			(s) => s.status !== 200,
+			async () => {
+				const r = await fetch(`https://${workerName}.${workersDev}`);
+				return { text: await r.text(), status: r.status };
+			}
 		);
-		expect(responseText).toMatchInlineSnapshot('"Hello World!"');
+		expect(text).toMatchInlineSnapshot('"Hello World!"');
 	});
 
 	it("modify & deploy worker", async () => {
@@ -94,10 +98,14 @@ describe("deploy", () => {
 		expect(stderr).toMatchInlineSnapshot('""');
 		workersDev = matchWorkersDev(stdout);
 
-		const responseText = await retry("Hello World!", () =>
-			fetch(`https://${workerName}.${workersDev}`).then((r) => r.text())
+		const { text } = await retry(
+			(s) => s.status !== 200 || s.text === "Hello World!",
+			async () => {
+				const r = await fetch(`https://${workerName}.${workersDev}`);
+				return { text: await r.text(), status: r.status };
+			}
 		);
-		expect(responseText).toMatchInlineSnapshot('"Updated Worker!"');
+		expect(text).toMatchInlineSnapshot('"Updated Worker!"');
 	});
 
 	it("delete worker", async () => {
@@ -108,8 +116,12 @@ describe("deploy", () => {
 			Successfully deleted smoke-test-worker"
 		`);
 		expect(stderr).toMatchInlineSnapshot('""');
-		const status = await retry(200, () =>
-			fetch(`https://${workerName}.${workersDev}`).then((r) => r.status)
+		const { status } = await retry(
+			(s) => s.status === 200 || s.status === 500,
+			async () => {
+				const r = await fetch(`https://${workerName}.${workersDev}`);
+				return { text: await r.text(), status: r.status };
+			}
 		);
 		expect(status).toBe(404);
 	});
diff --git a/packages/wrangler/e2e/deployments.test.ts b/packages/wrangler/e2e/deployments.test.ts
index 1c0006db07b1..f370b956a8d0 100644
--- a/packages/wrangler/e2e/deployments.test.ts
+++ b/packages/wrangler/e2e/deployments.test.ts
@@ -41,7 +41,7 @@ describe("deployments", () => {
 				[workerName]: "smoke-test-worker",
 				[email]: "person@example.com",
 			});
-	});
+	}, 50_000);
 
 	it("init worker", async () => {
 		const { stdout } =
@@ -78,10 +78,14 @@ describe("deployments", () => {
 		expect(stderr).toMatchInlineSnapshot('""');
 		workersDev = matchWorkersDev(stdout);
 
-		const responseText = await retry("", () =>
-			fetch(`https://${workerName}.${workersDev}`).then((r) => r.text())
+		const { text } = await retry(
+			(s) => s.status !== 200,
+			async () => {
+				const r = await fetch(`https://${workerName}.${workersDev}`);
+				return { text: await r.text(), status: r.status };
+			}
 		);
-		expect(responseText).toMatchInlineSnapshot('"Hello World!"');
+		expect(text).toMatchInlineSnapshot('"Hello World!"');
 	});
 
 	it("list 1 deployment", async () => {
@@ -119,10 +123,14 @@ describe("deployments", () => {
 		expect(stderr).toMatchInlineSnapshot('""');
 		workersDev = matchWorkersDev(stdout);
 
-		const responseText = await retry("Hello World!", () =>
-			fetch(`https://${workerName}.${workersDev}`).then((r) => r.text())
+		const { text } = await retry(
+			(s) => s.status !== 200 || s.text === "Hello World!",
+			async () => {
+				const r = await fetch(`https://${workerName}.${workersDev}`);
+				return { text: await r.text(), status: r.status };
+			}
 		);
-		expect(responseText).toMatchInlineSnapshot('"Updated Worker!"');
+		expect(text).toMatchInlineSnapshot('"Updated Worker!"');
 	});
 
 	it("list 2 deployments", async () => {
@@ -186,8 +194,9 @@ describe("deployments", () => {
 			Successfully deleted smoke-test-worker"
 		`);
 		expect(stderr).toMatchInlineSnapshot('""');
-		const status = await retry(200, () =>
-			fetch(`https://${workerName}.${workersDev}`).then((r) => r.status)
+		const status = await retry(
+			(s) => s === 200 || s === 500,
+			() => fetch(`https://${workerName}.${workersDev}`).then((r) => r.status)
 		);
 		expect(status).toBe(404);
 	});
diff --git a/packages/wrangler/e2e/dev.test.ts b/packages/wrangler/e2e/dev.test.ts
index aa36d4cfa0d5..9d1115e994d7 100644
--- a/packages/wrangler/e2e/dev.test.ts
+++ b/packages/wrangler/e2e/dev.test.ts
@@ -22,7 +22,7 @@ async function runDevSession(
 		const bg = await shellac.env(process.env).bg`
 		in ${workerPath} {
 			exits {
-				$$ ${WRANGLER} dev ${flags} --port ${port}
+				$ ${WRANGLER} dev ${flags} --port ${port}
 			}
 		}
 			`;
@@ -66,10 +66,14 @@ describe("basic dev tests", () => {
 
 	it("can modify worker during dev session (local)", async () => {
 		await runDevSession(workerPath, "", async (port) => {
-			const responseText = await retry("", () =>
-				fetch(`http://127.0.0.1:${port}`).then((r) => r.text())
+			const { text } = await retry(
+				(s) => s.status !== 200,
+				async () => {
+					const r = await fetch(`http://127.0.0.1:${port}`);
+					return { text: await r.text(), status: r.status };
+				}
 			);
-			expect(responseText).toMatchInlineSnapshot('"Hello World!"');
+			expect(text).toMatchInlineSnapshot('"Hello World!"');
 
 			await seed(workerPath, {
 				"src/index.ts": dedent`
@@ -80,19 +84,27 @@ describe("basic dev tests", () => {
 						}`,
 			});
 
-			const response2Text = await retry("Hello World!", () =>
-				fetch(`http://127.0.0.1:${port}`).then((r) => r.text())
+			const { text: text2 } = await retry(
+				(s) => s.status !== 200 || s.text === "Hello World!",
+				async () => {
+					const r = await fetch(`http://127.0.0.1:${port}`);
+					return { text: await r.text(), status: r.status };
+				}
 			);
-			expect(response2Text).toMatchInlineSnapshot('"Updated Worker!"');
+			expect(text2).toMatchInlineSnapshot('"Updated Worker!"');
 		});
 	});
 
 	it("can modify worker during dev session (remote)", async () => {
 		await runDevSession(workerPath, "--remote --ip 127.0.0.1", async (port) => {
-			const responseText = await retry("", () =>
-				fetch(`http://127.0.0.1:${port}`).then((r) => r.text())
+			const { text } = await retry(
+				(s) => s.status !== 200 || s.text === "",
+				async () => {
+					const r = await fetch(`http://127.0.0.1:${port}`);
+					return { text: await r.text(), status: r.status };
+				}
 			);
-			expect(responseText).toMatchInlineSnapshot('"Hello World!"');
+			expect(text).toMatchInlineSnapshot('"Hello World!"');
 
 			await seed(workerPath, {
 				"src/index.ts": dedent`
@@ -104,12 +116,17 @@ describe("basic dev tests", () => {
 			});
 
 			// Give a bit of time for the change to propagate.
+			// Otherwise the process has a tendency to hang.
 			await setTimeout(5000);
 
-			const response2Text = await retry("Hello World!", () =>
-				fetch(`http://127.0.0.1:${port}`).then((r) => r.text())
+			const { text: text2 } = await retry(
+				(s) => s.status !== 200 || s.text === "Hello World!",
+				async () => {
+					const r = await fetch(`http://127.0.0.1:${port}`);
+					return { text: await r.text(), status: r.status };
+				}
 			);
-			expect(response2Text).toMatchInlineSnapshot('"Updated Worker!"');
+			expect(text2).toMatchInlineSnapshot('"Updated Worker!"');
 		});
 	});
 });
diff --git a/packages/wrangler/e2e/helpers/normalize.ts b/packages/wrangler/e2e/helpers/normalize.ts
index c8c2f62fa05b..5ca1f6c95ef1 100644
--- a/packages/wrangler/e2e/helpers/normalize.ts
+++ b/packages/wrangler/e2e/helpers/normalize.ts
@@ -104,7 +104,7 @@ export function stripTimings(stdout: string): string {
 export function npmStripTimings(stdout: string): string {
 	return stdout
 		.replace(
-			/added \d+ packages, and audited \d+ packages in \d+s/,
+			/added \d+ packages, and audited \d+ packages in [\dms]+/,
 			"added (N) packages, and audited (N) packages in (TIMINGS)"
 		)
 		.replace(
diff --git a/packages/wrangler/e2e/helpers/retry.ts b/packages/wrangler/e2e/helpers/retry.ts
index a8e803667998..d749998b6322 100644
--- a/packages/wrangler/e2e/helpers/retry.ts
+++ b/packages/wrangler/e2e/helpers/retry.ts
@@ -1,20 +1,22 @@
 import { setTimeout } from "node:timers/promises";
 
 export async function retry<T>(
-	originalState: T,
+	retryIf: (currentState: T) => boolean,
 	action: () => Promise<T>,
-	n = 20
+	n = 30
 ): Promise<T> {
+	const states: T[] = [];
 	while (n >= 0) {
 		try {
 			const currentState = await action();
-			if (currentState !== originalState) {
+			if (!retryIf(currentState)) {
 				return currentState;
 			}
-		} catch (e) {
-			await setTimeout(2_000);
-			n--;
-		}
+			states.push(currentState);
+		} catch {}
+		await setTimeout(2_000);
+		n--;
 	}
+	console.error(states);
 	throw new Error("Timed out waiting for state to change");
 }