diff --git a/.changeset/improve-asset-upload-retry-log.md b/.changeset/improve-asset-upload-retry-log.md
new file mode 100644
index 0000000000..3347e64632
--- /dev/null
+++ b/.changeset/improve-asset-upload-retry-log.md
@@ -0,0 +1,7 @@
+---
+"wrangler": patch
+---
+
+Improve the log message shown when an asset upload attempt fails and is retried
+
+The retry message now reports which attempt is being made (e.g. `Asset upload failed. Retrying... 1 of 5 attempts.`), making it easier to gauge how close Wrangler is to exhausting its retry budget. The raw error object is no longer appended to this user-facing message; it is instead logged at debug level (visible via `WRANGLER_LOG=debug`).
diff --git a/packages/wrangler/src/__tests__/deploy/assets.test.ts b/packages/wrangler/src/__tests__/deploy/assets.test.ts
index 44e18c714b..0c9644b400 100644
--- a/packages/wrangler/src/__tests__/deploy/assets.test.ts
+++ b/packages/wrangler/src/__tests__/deploy/assets.test.ts
@@ -1326,5 +1326,76 @@ describe("deploy", () => {
 				`[Error: An unexpected response has been received from the Cloudflare API for assets upload. Please try again.]`
 			);
 		});
+
+		it("should retry asset uploads on failure and log a retry message including the attempt count", async ({
+			expect,
+		}) => {
+			vi.stubEnv("WRANGLER_LOG", "debug");
+
+			const assets = [{ filePath: "file-1.txt", content: "Content of file-1" }];
+			writeAssets(assets);
+			writeWranglerConfig({
+				assets: { directory: "assets" },
+			});
+
+			const mockBuckets = [["0de3dd5df907418e9730fd2bd747bd5e"]];
+			await mockAUSRequest([], mockBuckets, "<<aus-token>>");
+
+			// Fail the first upload attempt, succeed on the second.
+			const uploadAttempts: Request[] = [];
+			msw.use(
+				http.post(
+					"*/accounts/some-account-id/workers/assets/upload",
+					async ({ request }) => {
+						uploadAttempts.push(request);
+						if (uploadAttempts.length === 1) {
+							return HttpResponse.json(
+								{
+									success: false,
+									errors: [{ code: 1, message: "upload-boom-from-test" }],
+									messages: [],
+									result: null,
+								},
+								{ status: 500 }
+							);
+						}
+						return HttpResponse.json(
+							{
+								success: true,
+								errors: [],
+								messages: [],
+								result: { jwt: "<<aus-completion-token>>" },
+							},
+							{ status: 201 }
+						);
+					}
+				)
+			);
+
+			mockSubDomainRequest();
+			mockUploadWorkerRequest({
+				expectedAssets: {
+					jwt: "<<aus-completion-token>>",
+					config: {},
+				},
+				expectedType: "none",
+			});
+
+			await runWrangler("deploy");
+
+			// The upload endpoint was hit twice: once failing, once succeeding.
+			expect(uploadAttempts.length).toBe(2);
+
+			// The new info message includes the attempt count.
+			expect(std.info).toContain(
+				"Asset upload failed. Retrying... 1 of 5 attempts."
+			);
+
+			// The error details no longer leak into the user-facing info log.
+			expect(std.info).not.toContain("upload-boom-from-test");
+
+			// The error is now logged at debug level instead.
+			expect(std.debug).toContain("upload-boom-from-test");
+		});
 	});
 });
diff --git a/packages/wrangler/src/assets.ts b/packages/wrangler/src/assets.ts
index 7637ef9f0e..42b1cd88c0 100644
--- a/packages/wrangler/src/assets.ts
+++ b/packages/wrangler/src/assets.ts
@@ -193,7 +193,12 @@ export const syncAssets = async (
 				return res;
 			} catch (e) {
 				if (attempts < MAX_UPLOAD_ATTEMPTS) {
-					logger.info(chalk.dim(`Asset upload failed. Retrying...\n`, e));
+					logger.info(
+						chalk.dim(
+							`Asset upload failed. Retrying... ${attempts + 1} of ${MAX_UPLOAD_ATTEMPTS} attempts.\n`
+						)
+					);
+					logger.debug(e);
 					// Exponential backoff, 1 second first time, then 2 second, then 4 second etc.
 					await new Promise((resolvePromise) =>
 						setTimeout(resolvePromise, Math.pow(2, attempts) * 1000)