diff --git a/site/src/contexts/useProxyLatency.ts b/site/src/contexts/useProxyLatency.ts
index a3f63f213063c..ae1d26edbf380 100644
--- a/site/src/contexts/useProxyLatency.ts
+++ b/site/src/contexts/useProxyLatency.ts
@@ -1,7 +1,7 @@
 import { useEffect, useReducer, useState } from "react";
 import { API } from "#/api/api";
 import type { Region } from "#/api/typesGenerated";
-import { generateRandomString } from "#/utils/random";
+import { generateRandomBase64String } from "#/utils/random";
 
 const proxyIntervalSeconds = 30; // seconds
 
@@ -133,7 +133,7 @@ export const useProxyLatency = (
 				// Add a random query param to the url to make sure we don't get a cached response.
 				// This is important in case there is some caching layer between us and the proxy.
 				const url = new URL(
-					`/latency-check?cache_bust=${generateRandomString(6)}`,
+					`/latency-check?cache_bust=${generateRandomBase64String(6)}`,
 					proxy.path_app_url,
 				);
 				acc[url.toString()] = proxy;
diff --git a/site/src/pages/UsersPage/UsersPage.tsx b/site/src/pages/UsersPage/UsersPage.tsx
index 2151dc954db9b..37144254673f4 100644
--- a/site/src/pages/UsersPage/UsersPage.tsx
+++ b/site/src/pages/UsersPage/UsersPage.tsx
@@ -25,7 +25,7 @@ import { shouldShowAISeatColumn } from "#/modules/dashboard/entitlements";
 import { useDashboard } from "#/modules/dashboard/useDashboard";
 import { RoleSelectorDialog } from "#/modules/roles/RoleSelectorDialog";
 import { pageTitle } from "#/utils/page";
-import { generateRandomString } from "#/utils/random";
+import { generateRandomBase64String } from "#/utils/random";
 import { ResetPasswordDialog } from "./ResetPasswordDialog";
 import { UsersPageView } from "./UsersPageView";
 
@@ -122,7 +122,7 @@ const UsersPage: React.FC = () => {
 						newPassword:
 							process.env.STORYBOOK === "true"
 								? "hello-storybook"
-								: generateRandomString(12),
+								: generateRandomBase64String(12),
 					});
 				}}
 				onSuspendUser={setUserToSuspend}
diff --git a/site/src/utils/random.test.ts b/site/src/utils/random.test.ts
new file mode 100644
index 0000000000000..99efb5ef7461a
--- /dev/null
+++ b/site/src/utils/random.test.ts
@@ -0,0 +1,23 @@
+import { describe, expect, it } from "vitest";
+import { generateConnectionSessionId } from "#/utils/random";
+
+describe("generateConnectionSessionId", () => {
+	it("is 32 characters long", () => {
+		const id = generateConnectionSessionId();
+		expect(id.length).toBe(32);
+	});
+
+	it("outputs a hexadecimal string", () => {
+		const id = generateConnectionSessionId();
+		const hexRegex = /^[\da-f]+$/;
+		expect(hexRegex.test(id)).toBe(true);
+	});
+
+	it("generates unique values across calls", () => {
+		const numValues = 1000;
+		const ids = new Set(
+			Array.from({ length: numValues }, () => generateConnectionSessionId()),
+		);
+		expect(ids.size).toBe(numValues);
+	});
+});
diff --git a/site/src/utils/random.ts b/site/src/utils/random.ts
index 6a995b29393d6..39cfed9041623 100644
--- a/site/src/utils/random.ts
+++ b/site/src/utils/random.ts
@@ -1,3 +1,13 @@
+/**
+ * Generate a random hexadecimal string from the specified number of bytes.
+ */
+const generateRandomString = (bytes: number): string => {
+	const byteArr = crypto.getRandomValues(new Uint8Array(bytes));
+	return [...byteArr]
+		.map((byte) => byte.toString(16).padStart(2, "0"))
+		.join("");
+};
+
 /**
  * Generate a cryptographically secure random string using the specified number
  * of bytes then encode with base64.
@@ -6,14 +16,14 @@
  * equal the number of randomly generated bytes.
  * @see <https://developer.mozilla.org/en-US/docs/Glossary/Base64#encoded_size_increase>
  */
-export const generateRandomString = (bytes: number): string => {
-	const byteArr = window.crypto.getRandomValues(new Uint8Array(bytes));
-	// The types for `map` don't seem to support mapping from one array type to
-	// another and `String.fromCharCode.apply` wants `number[]` so loop like this
-	// instead.
-	const strArr: string[] = [];
-	for (const byte of byteArr) {
-		strArr.push(String.fromCharCode(byte));
-	}
-	return btoa(strArr.join(""));
+export const generateRandomBase64String = (bytes: number): string => {
+	return btoa(generateRandomString(bytes));
+};
+
+/**
+ * Generate a 16-byte (32-character) hexadecimal string for identifying
+ * workspace connection sessions.
+ */
+export const generateConnectionSessionId = (): string => {
+	return generateRandomString(16);
 };