diff --git a/.changeset/green-bugs-shout.md b/.changeset/green-bugs-shout.md
new file mode 100644
index 000000000000..2e48c1609c10
--- /dev/null
+++ b/.changeset/green-bugs-shout.md
@@ -0,0 +1,5 @@
+---
+"wrangler": patch
+---
+
+Simplify ENOENT debug logs for `.env` files
diff --git a/packages/wrangler/src/__tests__/dev.test.ts b/packages/wrangler/src/__tests__/dev.test.ts
index b41373492799..645630880925 100644
--- a/packages/wrangler/src/__tests__/dev.test.ts
+++ b/packages/wrangler/src/__tests__/dev.test.ts
@@ -1118,6 +1118,17 @@ describe.sequential("wrangler dev", () => {
 					__DOT_ENV_TEST_CUSTOM_BUILD_VAR_LOCAL=other-local"
 				`);
 			});
+
+			it("should show reasonable debug output if `.env` does not exist", async () => {
+				fs.rmSync(".env");
+				writeWranglerConfig({
+					main: "index.js",
+				});
+				await runWranglerUntilConfig("dev --log-level debug");
+				expect(std.debug).toContain(
+					'.env file not found at "<cwd>/.env". Continuing... For more details, refer to https://developers.cloudflare.com/workers/wrangler/system-environment-variables/'
+				);
+			});
 		});
 	});
 
diff --git a/packages/wrangler/src/config/dot-env.ts b/packages/wrangler/src/config/dot-env.ts
index a890878de844..7d6a1f3b3cb8 100644
--- a/packages/wrangler/src/config/dot-env.ts
+++ b/packages/wrangler/src/config/dot-env.ts
@@ -49,7 +49,13 @@ export function loadDotEnv(
 			override: true,
 		});
 		if (error) {
-			logger.debug(`Failed to load .env file "${envPath}":`, error);
+			if ("code" in error && error.code === "ENOENT") {
+				logger.debug(
+					`.env file not found at "${envPath}". Continuing... For more details, refer to https://developers.cloudflare.com/workers/wrangler/system-environment-variables/`
+				);
+			} else {
+				logger.debug(`Failed to load .env file "${envPath}":`, error);
+			}
 		} else if (parsed && !silent) {
 			const relativePath = path.relative(process.cwd(), envPath);
 			logger.log(`Using vars defined in ${relativePath}`);