diff --git a/src/remote/proxyCommandRetry.ts b/src/remote/proxyCommandRetry.ts
new file mode 100644
index 00000000..83ecce72
--- /dev/null
+++ b/src/remote/proxyCommandRetry.ts
@@ -0,0 +1,71 @@
+import * as fs from "node:fs/promises";
+import * as path from "node:path";
+
+import { renameWithRetry, tempFilePath } from "../util";
+
+import type { Logger } from "../logging/logger";
+
+/**
+ * POSIX shell script that wraps `coder ssh` with retry logic for the SSH
+ * ProxyCommand. After sleep/wake, DNS failures cause `coder ssh` to exit
+ * instantly, producing unparsable output that the Remote SSH extension
+ * treats as a permanent error ("Reload Window"). Retrying with a delay
+ * allows DNS to recover, including across system suspend/resume.
+ *
+ * Only retries when the command exits quickly (< CODER_RETRY_MIN_RUNTIME).
+ */
+const RETRY_SCRIPT = `#!/bin/sh
+# Coder SSH ProxyCommand retry wrapper.
+# Written by the Coder VS Code extension; do not edit.
+max_retries=\${CODER_RETRY_MAX_RETRIES:-10}
+retry_sleep=\${CODER_RETRY_SLEEP:-5}
+min_runtime=\${CODER_RETRY_MIN_RUNTIME:-10}
+n=0
+while [ $n -lt $max_retries ]; do
+    start=$(date +%s)
+    "$@"
+    rc=$?
+    elapsed=$(($(date +%s) - start))
+    [ $elapsed -ge $min_runtime ] && exit $rc
+    [ $rc -eq 0 ] && exit 0
+    n=$((n + 1))
+    echo "coder-retry: attempt $n/$max_retries failed (rc=$rc, elapsed=\${elapsed}s)" >&2
+    [ $n -lt $max_retries ] && sleep $retry_sleep
+done
+exit "$rc"
+`;
+
+const SCRIPT_NAME = "coder-ssh-retry.sh";
+
+/**
+ * Ensure the retry wrapper script exists on disk and return its path.
+ */
+export async function ensureRetryScript(
+	baseDir: string,
+	logger: Logger,
+): Promise<string> {
+	await fs.mkdir(baseDir, { recursive: true });
+	const scriptPath = path.join(baseDir, SCRIPT_NAME);
+
+	// Atomic write: temp file + rename to avoid races between concurrent
+	// VS Code windows writing the same script simultaneously.
+	const tmpPath = tempFilePath(scriptPath, "tmp");
+	await fs.writeFile(tmpPath, RETRY_SCRIPT, { mode: 0o755 });
+	try {
+		await renameWithRetry(
+			(src, dest) => fs.rename(src, dest),
+			tmpPath,
+			scriptPath,
+		);
+	} catch (error) {
+		await fs.unlink(tmpPath).catch((unlinkErr: NodeJS.ErrnoException) => {
+			if (unlinkErr.code !== "ENOENT") {
+				logger.warn("Failed to clean up temp retry script", tmpPath, unlinkErr);
+			}
+		});
+		throw new Error(`Failed to write retry script to ${scriptPath}`, {
+			cause: error,
+		});
+	}
+	return scriptPath;
+}
diff --git a/src/remote/remote.ts b/src/remote/remote.ts
index e482725a..06d5d31c 100644
--- a/src/remote/remote.ts
+++ b/src/remote/remote.ts
@@ -51,6 +51,7 @@ import {
 import { vscodeProposed } from "../vscodeProposed";
 import { WorkspaceMonitor } from "../workspace/workspaceMonitor";
 
+import { ensureRetryScript } from "./proxyCommandRetry";
 import {
 	SshConfig,
 	type SSHValues,
@@ -660,8 +661,8 @@ export class Remote {
 
 	/**
 	 * Builds the ProxyCommand for SSH connections to Coder workspaces.
-	 * Uses `coder ssh` for modern deployments with wildcard support,
-	 * or falls back to `coder vscodessh` for older deployments.
+	 * On macOS/Linux, wraps with a retry script to survive transient DNS
+	 * failures after sleep/wake (see proxyCommandRetry.ts).
 	 */
 	private async buildProxyCommand(
 		binaryPath: string,
@@ -670,6 +671,41 @@ export class Remote {
 		logDir: string,
 		useWildcardSSH: boolean,
 		cliAuth: CliAuth,
+	): Promise<string> {
+		const coderCommand = await this.buildCoderCommand(
+			binaryPath,
+			label,
+			hostPrefix,
+			logDir,
+			useWildcardSSH,
+			cliAuth,
+		);
+
+		if (os.platform() === "win32") {
+			return coderCommand;
+		}
+		try {
+			const retryScript = await ensureRetryScript(
+				this.pathResolver.getGlobalConfigDir(""),
+				this.logger,
+			);
+			return `${escapeCommandArg(retryScript)} ${coderCommand}`;
+		} catch (error) {
+			this.logger.warn("Failed to write retry wrapper, skipping", error);
+			return coderCommand;
+		}
+	}
+
+	/**
+	 * Builds the raw `coder ssh` or `coder vscodessh` command string.
+	 */
+	private async buildCoderCommand(
+		binaryPath: string,
+		label: string,
+		hostPrefix: string,
+		logDir: string,
+		useWildcardSSH: boolean,
+		cliAuth: CliAuth,
 	): Promise<string> {
 		const vscodeConfig = vscode.workspace.getConfiguration();
 
@@ -678,8 +714,7 @@ export class Remote {
 		const logArgs = await this.getLogArgs(logDir);
 
 		if (useWildcardSSH) {
-			// User SSH flags are included first; internally-managed flags
-			// are appended last so they take precedence.
+			// User SSH flags first; internal flags last so they take precedence.
 			const userSshFlags = getSshFlags(vscodeConfig);
 			// Make sure to update the `coder.sshFlags` description if we add more internal flags here!
 			const internalFlags = [
@@ -695,28 +730,28 @@ export class Remote {
 
 			const allFlags = [...userSshFlags, ...internalFlags];
 			return `${escapedBinaryPath} ${globalConfig.join(" ")} ssh ${allFlags.join(" ")}`;
-		} else {
-			const networkInfoDir = escapeCommandArg(
-				this.pathResolver.getNetworkInfoPath(),
-			);
-			const sessionTokenFile = escapeCommandArg(
-				this.pathResolver.getSessionTokenPath(label),
-			);
-			const urlFile = escapeCommandArg(this.pathResolver.getUrlPath(label));
+		}
 
-			const sshFlags = [
-				"--network-info-dir",
-				networkInfoDir,
-				...logArgs,
-				"--session-token-file",
-				sessionTokenFile,
-				"--url-file",
-				urlFile,
-				"%h",
-			];
+		const networkInfoDir = escapeCommandArg(
+			this.pathResolver.getNetworkInfoPath(),
+		);
+		const sessionTokenFile = escapeCommandArg(
+			this.pathResolver.getSessionTokenPath(label),
+		);
+		const urlFile = escapeCommandArg(this.pathResolver.getUrlPath(label));
+
+		const sshFlags = [
+			"--network-info-dir",
+			networkInfoDir,
+			...logArgs,
+			"--session-token-file",
+			sessionTokenFile,
+			"--url-file",
+			urlFile,
+			"%h",
+		];
 
-			return `${escapedBinaryPath} ${globalConfig.join(" ")} vscodessh ${sshFlags.join(" ")}`;
-		}
+		return `${escapedBinaryPath} ${globalConfig.join(" ")} vscodessh ${sshFlags.join(" ")}`;
 	}
 
 	/**
diff --git a/test/unit/remote/proxyCommandRetry.test.ts b/test/unit/remote/proxyCommandRetry.test.ts
new file mode 100644
index 00000000..bc28350c
--- /dev/null
+++ b/test/unit/remote/proxyCommandRetry.test.ts
@@ -0,0 +1,109 @@
+import { execFile } from "node:child_process";
+import * as fs from "node:fs/promises";
+import * as os from "node:os";
+import * as path from "node:path";
+import { promisify } from "node:util";
+import { afterEach, beforeEach, describe, expect, it } from "vitest";
+
+import { ensureRetryScript } from "@/remote/proxyCommandRetry";
+
+import { createMockLogger } from "../../mocks/testHelpers";
+import { isWindows } from "../../utils/platform";
+
+const execFileAsync = promisify(execFile);
+
+/** Run the retry script with fast defaults (0s sleep). */
+function run(
+	script: string,
+	args: string[],
+	env: Record<string, string> = {},
+	timeout?: number,
+) {
+	return execFileAsync(script, args, {
+		timeout,
+		env: {
+			...process.env,
+			CODER_RETRY_SLEEP: "0",
+			CODER_RETRY_MAX_RETRIES: "10",
+			CODER_RETRY_MIN_RUNTIME: "10",
+			...env,
+		},
+	});
+}
+
+describe.skipIf(isWindows())("proxyCommandRetry", () => {
+	let tmpDir: string;
+	let script: string;
+
+	beforeEach(async () => {
+		tmpDir = await fs.mkdtemp(path.join(os.tmpdir(), "coder-retry-test-"));
+		script = await ensureRetryScript(tmpDir, createMockLogger());
+	});
+
+	afterEach(async () => {
+		await fs.rm(tmpDir, { recursive: true, force: true });
+	});
+
+	it("passes through on success", async () => {
+		const { stdout } = await run(script, ["echo", "hello"]);
+		expect(stdout.trim()).toBe("hello");
+	});
+
+	it("retries on quick failure then succeeds", async () => {
+		// Fails until marker file exists, then succeeds.
+		const marker = path.join(tmpDir, "marker");
+		const helper = path.join(tmpDir, "h.sh");
+		await fs.writeFile(
+			helper,
+			`#!/bin/sh\n[ -f "${marker}" ] && echo ok && exit 0\ntouch "${marker}"\nexit 1\n`,
+			{ mode: 0o755 },
+		);
+
+		const { stdout } = await run(script, [helper]);
+		expect(stdout.trim()).toBe("ok");
+	});
+
+	it("gives up after max retries and logs each attempt", async () => {
+		try {
+			await run(script, ["sh", "-c", "exit 42"], {
+				CODER_RETRY_MAX_RETRIES: "3",
+			});
+			expect.fail("should have thrown");
+		} catch (err: unknown) {
+			const e = err as { code: number; stderr: string };
+			expect(e.code).toBe(42);
+			expect(e.stderr).toContain("attempt 1/3 failed");
+			expect(e.stderr).toContain("attempt 3/3 failed");
+		}
+	});
+
+	it("skips retry when command ran longer than min runtime", async () => {
+		const marker = path.join(tmpDir, "ran");
+		const helper = path.join(tmpDir, "slow.sh");
+		await fs.writeFile(
+			helper,
+			`#!/bin/sh\n[ -f "${marker}" ] && exit 99\ntouch "${marker}"\nsleep 2\nexit 1\n`,
+			{ mode: 0o755 },
+		);
+
+		try {
+			await run(script, [helper], { CODER_RETRY_MIN_RUNTIME: "1" }, 10000);
+			expect.fail("should have thrown");
+		} catch (err: unknown) {
+			// Exit code 1 (not 99) proves it ran once and didn't retry.
+			expect((err as { code: number }).code).toBe(1);
+		}
+	});
+
+	it("preserves arguments with spaces", async () => {
+		const { stdout } = await run(script, [
+			"sh",
+			"-c",
+			'echo "$1 $2"',
+			"--",
+			"hello world",
+			"it's fine",
+		]);
+		expect(stdout.trim()).toBe("hello world it's fine");
+	});
+});