diff --git a/site/e2e/tests/deployment/security.spec.ts b/site/e2e/tests/deployment/security.spec.ts
new file mode 100644
index 0000000000..fe88dcfba2
--- /dev/null
+++ b/site/e2e/tests/deployment/security.spec.ts
@@ -0,0 +1,71 @@
+import { expect, test, type Page } from "@playwright/test";
+import * as API from "api/api";
+import { setupApiCalls } from "../../api";
+
+test("enabled security settings", async ({ page }) => {
+  await setupApiCalls(page);
+
+  const config = await API.getDeploymentConfig();
+
+  await page.goto("/deployment/security", { waitUntil: "domcontentloaded" });
+
+  const flags = [
+    "ssh-keygen-algorithm",
+    "secure-auth-cookie",
+    "disable-owner-workspace-access",
+
+    "tls-redirect-http-to-https",
+    "strict-transport-security",
+    "tls-address",
+    "tls-allow-insecure-ciphers",
+    "tls-client-auth",
+    "tls-enable",
+    "tls-min-version",
+  ];
+
+  for (const flag of flags) {
+    await verifyConfigFlag(page, config, flag);
+  }
+});
+
+const verifyConfigFlag = async (
+  page: Page,
+  config: API.DeploymentConfig,
+  flag: string,
+) => {
+  const opt = config.options.find((option) => option.flag === flag);
+  if (opt === undefined) {
+    throw new Error(`Option with env ${flag} has undefined value.`);
+  }
+
+  // Map option type to test class name.
+  let type = "",
+    value = opt.value;
+  if (typeof value === "boolean") {
+    // Boolean options map to string (Enabled/Disabled).
+    type = value ? "option-enabled" : "option-disabled";
+    value = value ? "Enabled" : "Disabled";
+  } else if (typeof value === "number") {
+    type = "option-value-number";
+    value = String(value);
+  } else if (!value || value.length === 0) {
+    type = "option-value-empty";
+  } else if (typeof value === "string") {
+    type = "option-value-string";
+  } else if (typeof value === "object") {
+    type = "object-array";
+  } else {
+    type = "option-value-json";
+  }
+
+  // Special cases
+  if (opt.flag === "strict-transport-security" && opt.value === 0) {
+    type = "option-value-string";
+    value = "Disabled"; // Display "Disabled" instead of zero seconds.
+  }
+
+  const configOption = page.locator(
+    `div.options-table .option-${flag} .${type}`,
+  );
+  await expect(configOption).toHaveText(String(value));
+};
diff --git a/site/src/components/Badges/Badges.tsx b/site/src/components/Badges/Badges.tsx
index 152e7735fd..7fc76fb879 100644
--- a/site/src/components/Badges/Badges.tsx
+++ b/site/src/components/Badges/Badges.tsx
@@ -41,7 +41,11 @@ const styles = {
 } satisfies Record<string, Interpolation<Theme>>;
 
 export const EnabledBadge: FC = () => {
-  return <span css={[styles.badge, styles.enabledBadge]}>Enabled</span>;
+  return (
+    <span css={[styles.badge, styles.enabledBadge]} className="option-enabled">
+      Enabled
+    </span>
+  );
 };
 
 export const EntitledBadge: FC = () => {
@@ -95,6 +99,7 @@ export const DisabledBadge: FC = forwardRef<
           color: theme.experimental.l1.text,
         }),
       ]}
+      className="option-disabled"
     >
       Disabled
     </span>
diff --git a/site/src/pages/DeploySettingsPage/Option.tsx b/site/src/pages/DeploySettingsPage/Option.tsx
index 9e5e9f7abd..b79aeef3ab 100644
--- a/site/src/pages/DeploySettingsPage/Option.tsx
+++ b/site/src/pages/DeploySettingsPage/Option.tsx
@@ -34,19 +34,35 @@ export const OptionValue: FC<OptionValueProps> = (props) => {
   const theme = useTheme();
 
   if (typeof value === "boolean") {
-    return value ? <EnabledBadge /> : <DisabledBadge />;
+    return (
+      <div className="option-value-boolean">
+        {value ? <EnabledBadge /> : <DisabledBadge />}
+      </div>
+    );
   }
 
   if (typeof value === "number") {
-    return <span css={styles.option}>{value}</span>;
+    return (
+      <span css={styles.option} className="option-value-number">
+        {value}
+      </span>
+    );
   }
 
   if (!value || value.length === 0) {
-    return <span css={styles.option}>Not set</span>;
+    return (
+      <span css={styles.option} className="option-value-empty">
+        Not set
+      </span>
+    );
   }
 
   if (typeof value === "string") {
-    return <span css={styles.option}>{value}</span>;
+    return (
+      <span css={styles.option} className="option-value-string">
+        {value}
+      </span>
+    );
   }
 
   if (typeof value === "object" && !Array.isArray(value)) {
@@ -94,7 +110,7 @@ export const OptionValue: FC<OptionValueProps> = (props) => {
 
   if (Array.isArray(value)) {
     return (
-      <ul css={{ listStylePosition: "inside" }}>
+      <ul css={{ listStylePosition: "inside" }} className="option-array">
         {value.map((item) => (
           <li key={item} css={styles.option}>
             {item}
@@ -104,7 +120,11 @@ export const OptionValue: FC<OptionValueProps> = (props) => {
     );
   }
 
-  return <span css={styles.option}>{JSON.stringify(value)}</span>;
+  return (
+    <span css={styles.option} className="option-value-json">
+      {JSON.stringify(value)}
+    </span>
+  );
 };
 
 type OptionConfigProps = HTMLAttributes<HTMLDivElement> & { isSource: boolean };