diff --git a/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicenseCard.test.tsx b/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicenseCard.test.tsx
index 59f1182ac7..09737c1e98 100644
--- a/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicenseCard.test.tsx
+++ b/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicenseCard.test.tsx
@@ -1,6 +1,7 @@
 import { MockLicenseResponse } from "testHelpers/entities";
 import { render } from "testHelpers/renderHelpers";
 import { screen } from "@testing-library/react";
+import userEvent from "@testing-library/user-event";
 import { LicenseCard } from "./LicenseCard";
 
 describe("LicenseCard", () => {
@@ -40,6 +41,44 @@ describe("LicenseCard", () => {
 		await screen.findByText("Enterprise");
 	});
 
+	it("shows expired removal message for expired licenses", async () => {
+		const user = userEvent.setup();
+		render(
+			<LicenseCard
+				license={MockLicenseResponse[3]}
+				userLimitActual={1}
+				userLimitLimit={10}
+				onRemove={() => null}
+				isRemoving={false}
+			/>,
+		);
+
+		const removeButton = await screen.findByRole("button", { name: /remove/i });
+		await user.click(removeButton);
+
+		await screen.findByText(/This license has already expired/);
+	});
+
+	it("shows disabling features warning for active licenses", async () => {
+		const user = userEvent.setup();
+		render(
+			<LicenseCard
+				license={MockLicenseResponse[0]}
+				userLimitActual={1}
+				userLimitLimit={10}
+				onRemove={() => null}
+				isRemoving={false}
+			/>,
+		);
+
+		const removeButton = await screen.findByRole("button", { name: /remove/i });
+		await user.click(removeButton);
+
+		await screen.findByText(
+			/Removing this license will disable all Premium features/,
+		);
+	});
+
 	it("renders license's user_limit when it is available instead of using the default", async () => {
 		const licenseUserLimit = 3;
 		const license = {
diff --git a/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicenseCard.tsx b/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicenseCard.tsx
index 0a22317d75..15edcf5da4 100644
--- a/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicenseCard.tsx
+++ b/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicenseCard.tsx
@@ -29,6 +29,10 @@ export const LicenseCard: FC<LicenseCardProps> = ({
 
 	const currentUserLimit = license.claims.features.user_limit || userLimitLimit;
 
+	const isExpired = dayjs
+		.unix(license.claims.license_expires)
+		.isBefore(dayjs());
+
 	const licenseType = license.claims.trial
 		? "Trial"
 		: license.claims.feature_set?.toLowerCase() === "premium"
@@ -57,7 +61,11 @@ export const LicenseCard: FC<LicenseCardProps> = ({
 				title="Confirm License Removal"
 				confirmLoading={isRemoving}
 				confirmText="Remove"
-				description="Removing this license will disable all Premium features. You add a new license at any time."
+				description={
+					isExpired
+						? "This license has already expired and is not providing any features. Removing it will not affect your current entitlements."
+						: "Removing this license will disable all Premium features. You can add a new license at any time."
+				}
 			/>
 			<Stack
 				direction="row"
@@ -94,7 +102,7 @@ export const LicenseCard: FC<LicenseCardProps> = ({
 						</Stack>
 					)}
 					<Stack direction="column" spacing={0} alignItems="center">
-						{dayjs(license.claims.license_expires * 1000).isBefore(dayjs()) ? (
+						{isExpired ? (
 							<Pill css={styles.expiredBadge} type="error">
 								Expired
 							</Pill>