diff --git a/site/src/api/api.ts b/site/src/api/api.ts
index 5a314ddde151a..43051961fa7e7 100644
--- a/site/src/api/api.ts
+++ b/site/src/api/api.ts
@@ -804,7 +804,7 @@ class ApiMethods {
 	) => {
 		const params = new URLSearchParams();
 		params.set("claimField", field);
-		const response = await this.axios.get<TypesGen.Response>(
+		const response = await this.axios.get<readonly string[]>(
 			`/api/v2/organizations/${organization}/settings/idpsync/field-values?${params}`,
 		);
 		return response.data;
diff --git a/site/src/pages/DeploymentSettingsPage/IdpOrgSyncPage/IdpOrgSyncPageView.stories.tsx b/site/src/pages/DeploymentSettingsPage/IdpOrgSyncPage/IdpOrgSyncPageView.stories.tsx
index 78842737e5baf..430fce3a2ee05 100644
--- a/site/src/pages/DeploymentSettingsPage/IdpOrgSyncPage/IdpOrgSyncPageView.stories.tsx
+++ b/site/src/pages/DeploymentSettingsPage/IdpOrgSyncPage/IdpOrgSyncPageView.stories.tsx
@@ -1,5 +1,5 @@
 import type { Meta, StoryObj } from "@storybook/react";
-import { userEvent, within } from "@storybook/test";
+import { expect, userEvent, within } from "@storybook/test";
 import {
 	MockOrganization,
 	MockOrganization2,
@@ -45,10 +45,16 @@ export const MissingGroups: Story = {
 	},
 };
 
-export const MissingClaim: Story = {
+export const MissingClaims: Story = {
 	args: {
 		claimFieldValues: [],
 	},
+	play: async ({ canvasElement }) => {
+		const user = userEvent.setup();
+		const warning = canvasElement.querySelector(".lucide-triangle-alert")!;
+		expect(warning).not.toBe(null);
+		await user.hover(warning);
+	},
 };
 
 export const AssignDefaultOrgWarningDialog: Story = {
diff --git a/site/src/pages/DeploymentSettingsPage/IdpOrgSyncPage/IdpOrgSyncPageView.tsx b/site/src/pages/DeploymentSettingsPage/IdpOrgSyncPage/IdpOrgSyncPageView.tsx
index f6822ba0a60ef..bdcc65b89aaba 100644
--- a/site/src/pages/DeploymentSettingsPage/IdpOrgSyncPage/IdpOrgSyncPageView.tsx
+++ b/site/src/pages/DeploymentSettingsPage/IdpOrgSyncPage/IdpOrgSyncPageView.tsx
@@ -1,4 +1,3 @@
-import { TooltipProvider } from "@radix-ui/react-tooltip";
 import type {
 	Organization,
 	OrganizationSyncSettings,
@@ -30,7 +29,6 @@ import {
 	type Option,
 } from "components/MultiSelectCombobox/MultiSelectCombobox";
 import { Spinner } from "components/Spinner/Spinner";
-import { Stack } from "components/Stack/Stack";
 import { Switch } from "components/Switch/Switch";
 import {
 	Table,
@@ -42,6 +40,7 @@ import {
 import {
 	Tooltip,
 	TooltipContent,
+	TooltipProvider,
 	TooltipTrigger,
 } from "components/Tooltip/Tooltip";
 import { useFormik } from "formik";
diff --git a/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpGroupSyncForm.tsx b/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpGroupSyncForm.tsx
index 2f1c0be7fa602..9d63baf180fbc 100644
--- a/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpGroupSyncForm.tsx
+++ b/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpGroupSyncForm.tsx
@@ -22,8 +22,14 @@ import {
 } from "components/MultiSelectCombobox/MultiSelectCombobox";
 import { Spinner } from "components/Spinner/Spinner";
 import { Switch } from "components/Switch/Switch";
+import {
+	Tooltip,
+	TooltipContent,
+	TooltipProvider,
+	TooltipTrigger,
+} from "components/Tooltip/Tooltip";
 import { useFormik } from "formik";
-import { Plus, Trash } from "lucide-react";
+import { Plus, Trash, TriangleAlert } from "lucide-react";
 import { type FC, useId, useState } from "react";
 import { docs } from "utils/docs";
 import { isUUID } from "utils/uuid";
@@ -32,16 +38,6 @@ import { ExportPolicyButton } from "./ExportPolicyButton";
 import { IdpMappingTable } from "./IdpMappingTable";
 import { IdpPillList } from "./IdpPillList";
 
-interface IdpGroupSyncFormProps {
-	groupSyncSettings: GroupSyncSettings;
-	groupsMap: Map<string, string>;
-	groups: Group[];
-	groupMappingCount: number;
-	legacyGroupMappingCount: number;
-	organization: Organization;
-	onSubmit: (data: GroupSyncSettings) => void;
-}
-
 const groupSyncValidationSchema = Yup.object({
 	field: Yup.string().trim(),
 	regex_filter: Yup.string().trim(),
@@ -65,15 +61,27 @@ const groupSyncValidationSchema = Yup.object({
 		.default({}),
 });
 
-export const IdpGroupSyncForm = ({
+interface IdpGroupSyncFormProps {
+	groupSyncSettings: GroupSyncSettings;
+	claimFieldValues: readonly string[] | undefined;
+	groupsMap: Map<string, string>;
+	groups: Group[];
+	groupMappingCount: number;
+	legacyGroupMappingCount: number;
+	organization: Organization;
+	onSubmit: (data: GroupSyncSettings) => void;
+}
+
+export const IdpGroupSyncForm: FC<IdpGroupSyncFormProps> = ({
 	groupSyncSettings,
+	claimFieldValues,
 	groupMappingCount,
 	legacyGroupMappingCount,
 	groups,
 	groupsMap,
 	organization,
 	onSubmit,
-}: IdpGroupSyncFormProps) => {
+}) => {
 	const form = useFormik<GroupSyncSettings>({
 		initialValues: {
 			field: groupSyncSettings?.field ?? "",
@@ -270,6 +278,7 @@ export const IdpGroupSyncForm = ({
 									<GroupRow
 										key={idpGroup}
 										idpGroup={idpGroup}
+										exists={claimFieldValues?.includes(idpGroup)}
 										coderGroup={getGroupNames(groups)}
 										onDelete={handleDelete}
 									/>
@@ -288,6 +297,7 @@ export const IdpGroupSyncForm = ({
 										<GroupRow
 											key={groupId}
 											idpGroup={idpGroup}
+											exists={claimFieldValues?.includes(idpGroup)}
 											coderGroup={getGroupNames([groupId])}
 											onDelete={handleDelete}
 										/>
@@ -303,17 +313,48 @@ export const IdpGroupSyncForm = ({
 
 interface GroupRowProps {
 	idpGroup: string;
+	exists: boolean | undefined;
 	coderGroup: readonly string[];
 	onDelete: (idpOrg: string) => void;
 }
 
-const GroupRow: FC<GroupRowProps> = ({ idpGroup, coderGroup, onDelete }) => {
+const GroupRow: FC<GroupRowProps> = ({
+	idpGroup,
+	exists = true,
+	coderGroup,
+	onDelete,
+}) => {
 	return (
 		<TableRow data-testid={`group-${idpGroup}`}>
-			<TableCell>{idpGroup}</TableCell>
+			<TableCell>
+				<div className="flex flex-row items-center gap-2 text-content-primary">
+					{idpGroup}
+					{!exists && (
+						<TooltipProvider>
+							<Tooltip>
+								<TooltipTrigger asChild>
+									<TriangleAlert className="size-icon-xs cursor-pointer text-content-warning" />
+								</TooltipTrigger>
+								<TooltipContent
+									align="start"
+									alignOffset={-8}
+									sideOffset={8}
+									className="p-2 text-xs text-content-secondary max-w-sm"
+								>
+									This value has not be seen in the specified claim field
+									before. You might want to check your IdP configuration and
+									ensure that this value is not misspelled.
+								</TooltipContent>
+							</Tooltip>
+						</TooltipProvider>
+					)}
+				</div>
+			</TableCell>
+
 			<TableCell>
 				<IdpPillList roles={coderGroup} />
 			</TableCell>
+
 			<TableCell>
 				<Button
 					variant="outline"
diff --git a/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpRoleSyncForm.tsx b/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpRoleSyncForm.tsx
index ffe68e33e2ecc..c605decf47c58 100644
--- a/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpRoleSyncForm.tsx
+++ b/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpRoleSyncForm.tsx
@@ -9,22 +9,20 @@ import {
 	type Option,
 } from "components/MultiSelectCombobox/MultiSelectCombobox";
 import { Spinner } from "components/Spinner/Spinner";
+import {
+	Tooltip,
+	TooltipContent,
+	TooltipProvider,
+	TooltipTrigger,
+} from "components/Tooltip/Tooltip";
 import { useFormik } from "formik";
-import { Plus, Trash } from "lucide-react";
+import { Plus, Trash, TriangleAlert } from "lucide-react";
 import { type FC, useId, useState } from "react";
 import * as Yup from "yup";
 import { ExportPolicyButton } from "./ExportPolicyButton";
 import { IdpMappingTable } from "./IdpMappingTable";
 import { IdpPillList } from "./IdpPillList";
 
-interface IdpRoleSyncFormProps {
-	roleSyncSettings: RoleSyncSettings;
-	roleMappingCount: number;
-	organization: Organization;
-	roles: Role[];
-	onSubmit: (data: RoleSyncSettings) => void;
-}
-
 const roleSyncValidationSchema = Yup.object({
 	field: Yup.string().trim(),
 	regex_filter: Yup.string().trim(),
@@ -48,13 +46,23 @@ const roleSyncValidationSchema = Yup.object({
 		.default({}),
 });
 
-export const IdpRoleSyncForm = ({
+interface IdpRoleSyncFormProps {
+	roleSyncSettings: RoleSyncSettings;
+	claimFieldValues: readonly string[] | undefined;
+	roleMappingCount: number;
+	organization: Organization;
+	roles: Role[];
+	onSubmit: (data: RoleSyncSettings) => void;
+}
+
+export const IdpRoleSyncForm: FC<IdpRoleSyncFormProps> = ({
 	roleSyncSettings,
+	claimFieldValues,
 	roleMappingCount,
 	organization,
 	roles,
 	onSubmit,
-}: IdpRoleSyncFormProps) => {
+}) => {
 	const form = useFormik<RoleSyncSettings>({
 		initialValues: {
 			field: roleSyncSettings?.field ?? "",
@@ -210,6 +218,7 @@ export const IdpRoleSyncForm = ({
 								<RoleRow
 									key={idpRole}
 									idpRole={idpRole}
+									exists={claimFieldValues?.includes(idpRole)}
 									coderRoles={roles}
 									onDelete={handleDelete}
 								/>
@@ -222,17 +231,48 @@ export const IdpRoleSyncForm = ({
 
 interface RoleRowProps {
 	idpRole: string;
+	exists: boolean | undefined;
 	coderRoles: readonly string[];
 	onDelete: (idpOrg: string) => void;
 }
 
-const RoleRow: FC<RoleRowProps> = ({ idpRole, coderRoles, onDelete }) => {
+const RoleRow: FC<RoleRowProps> = ({
+	idpRole,
+	exists = true,
+	coderRoles,
+	onDelete,
+}) => {
 	return (
 		<TableRow data-testid={`role-${idpRole}`}>
-			<TableCell>{idpRole}</TableCell>
+			<TableCell>
+				<div className="flex flex-row items-center gap-2 text-content-primary">
+					{idpRole}
+					{!exists && (
+						<TooltipProvider>
+							<Tooltip>
+								<TooltipTrigger asChild>
+									<TriangleAlert className="size-icon-xs cursor-pointer text-content-warning" />
+								</TooltipTrigger>
+								<TooltipContent
+									align="start"
+									alignOffset={-8}
+									sideOffset={8}
+									className="p-2 text-xs text-content-secondary max-w-sm"
+								>
+									This value has not be seen in the specified claim field
+									before. You might want to check your IdP configuration and
+									ensure that this value is not misspelled.
+								</TooltipContent>
+							</Tooltip>
+						</TooltipProvider>
+					)}
+				</div>
+			</TableCell>
+
 			<TableCell>
 				<IdpPillList roles={coderRoles} />
 			</TableCell>
+
 			<TableCell>
 				<Button
 					variant="outline"
diff --git a/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPage.tsx b/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPage.tsx
index 1164558ef6586..723ea919d2e39 100644
--- a/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPage.tsx
+++ b/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPage.tsx
@@ -2,6 +2,7 @@ import { getErrorMessage } from "api/errors";
 import { groupsByOrganization } from "api/queries/groups";
 import {
 	groupIdpSyncSettings,
+	organizationIdpSyncClaimFieldValues,
 	patchGroupSyncSettings,
 	patchRoleSyncSettings,
 	roleIdpSyncSettings,
@@ -17,8 +18,8 @@ import { useFeatureVisibility } from "modules/dashboard/useFeatureVisibility";
 import { useOrganizationSettings } from "modules/management/OrganizationSettingsLayout";
 import type { FC } from "react";
 import { Helmet } from "react-helmet-async";
-import { useMutation, useQueries, useQueryClient } from "react-query";
-import { useParams } from "react-router-dom";
+import { useMutation, useQueries, useQuery, useQueryClient } from "react-query";
+import { useParams, useSearchParams } from "react-router-dom";
 import { docs } from "utils/docs";
 import { pageTitle } from "utils/page";
 import IdpSyncPageView from "./IdpSyncPageView";
@@ -47,6 +48,19 @@ export const IdpSyncPage: FC = () => {
 		],
 	});
 
+	const [searchParams] = useSearchParams();
+	const tab = searchParams.get("tab") || "groups";
+	const field =
+		tab === "groups"
+			? groupIdpSyncSettingsQuery.data?.field
+			: roleIdpSyncSettingsQuery.data?.field;
+
+	const fieldValuesQuery = useQuery(
+		field
+			? organizationIdpSyncClaimFieldValues(organizationName, field)
+			: { enabled: false },
+	);
+
 	if (!organization) {
 		return <EmptyState message="Organization not found" />;
 	}
@@ -99,8 +113,10 @@ export const IdpSyncPage: FC = () => {
 					</Cond>
 					<Cond>
 						<IdpSyncPageView
+							tab={tab}
 							groupSyncSettings={groupIdpSyncSettingsQuery.data}
 							roleSyncSettings={roleIdpSyncSettingsQuery.data}
+							claimFieldValues={fieldValuesQuery.data}
 							groups={groupsQuery.data}
 							groupsMap={groupsMap}
 							roles={rolesQuery.data}
diff --git a/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPageView.stories.tsx b/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPageView.stories.tsx
index ec5cc299c645c..759d84a039b71 100644
--- a/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPageView.stories.tsx
+++ b/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPageView.stories.tsx
@@ -1,5 +1,5 @@
 import type { Meta, StoryObj } from "@storybook/react";
-import { expect, userEvent, within } from "@storybook/test";
+import { expect, userEvent } from "@storybook/test";
 import {
 	MockGroup,
 	MockGroup2,
@@ -11,20 +11,32 @@ import {
 } from "testHelpers/entities";
 import { IdpSyncPageView } from "./IdpSyncPageView";
 
+const groupsMap = new Map<string, string>();
+for (const group of [MockGroup, MockGroup2]) {
+	groupsMap.set(group.id, group.display_name || group.name);
+}
+
 const meta: Meta<typeof IdpSyncPageView> = {
 	title: "pages/IdpSyncPage",
 	component: IdpSyncPageView,
+	args: {
+		tab: "groups",
+		groupSyncSettings: MockGroupSyncSettings,
+		roleSyncSettings: MockRoleSyncSettings,
+		claimFieldValues: [
+			...Object.keys(MockGroupSyncSettings.mapping),
+			...Object.keys(MockRoleSyncSettings.mapping),
+		],
+		groups: [MockGroup, MockGroup2],
+		groupsMap,
+		organization: MockOrganization,
+		error: undefined,
+	},
 };
 
 export default meta;
 type Story = StoryObj<typeof IdpSyncPageView>;
 
-const groupsMap = new Map<string, string>();
-
-for (const group of [MockGroup, MockGroup2]) {
-	groupsMap.set(group.id, group.display_name || group.name);
-}
-
 export const Empty: Story = {
 	args: {
 		groupSyncSettings: {
@@ -44,47 +56,56 @@ export const Empty: Story = {
 	},
 };
 
-export const Default: Story = {
-	args: {
-		groupSyncSettings: MockGroupSyncSettings,
-		roleSyncSettings: MockRoleSyncSettings,
-		groups: [MockGroup, MockGroup2],
-		groupsMap,
-		organization: MockOrganization,
-		error: undefined,
-	},
-};
+export const Default: Story = {};
 
 export const HasError: Story = {
 	args: {
-		...Default.args,
 		error: "This is a test error",
 	},
 };
 
 export const MissingGroups: Story = {
 	args: {
-		...Default.args,
 		groupSyncSettings: MockGroupSyncSettings2,
 	},
 };
 
 export const WithLegacyMapping: Story = {
 	args: {
-		...Default.args,
 		groupSyncSettings: MockLegacyMappingGroupSyncSettings,
+		claimFieldValues: Object.keys(
+			MockLegacyMappingGroupSyncSettings.legacy_group_name_mapping,
+		),
+	},
+};
+
+export const GroupsTabMissingClaims: Story = {
+	args: {
+		claimFieldValues: [],
+	},
+	play: async ({ canvasElement }) => {
+		const user = userEvent.setup();
+		const warning = canvasElement.querySelector(".lucide-triangle-alert")!;
+		expect(warning).not.toBe(null);
+		await user.hover(warning);
 	},
 };
 
 export const RolesTab: Story = {
 	args: {
-		...Default.args,
+		tab: "roles",
+	},
+};
+
+export const RolesTabMissingClaims: Story = {
+	args: {
+		tab: "roles",
+		claimFieldValues: [],
 	},
 	play: async ({ canvasElement }) => {
 		const user = userEvent.setup();
-		const canvas = within(canvasElement);
-		const rolesTab = await canvas.findByText("Role sync settings");
-		await user.click(rolesTab);
-		await expect(canvas.findByText("IdP role")).resolves.toBeVisible();
+		const warning = canvasElement.querySelector(".lucide-triangle-alert")!;
+		expect(warning).not.toBe(null);
+		await user.hover(warning);
 	},
 };
diff --git a/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPageView.tsx b/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPageView.tsx
index 18e1fd96fbdff..b196b0a09c600 100644
--- a/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPageView.tsx
+++ b/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPageView.tsx
@@ -9,13 +9,14 @@ import { ErrorAlert } from "components/Alert/ErrorAlert";
 import { Loader } from "components/Loader/Loader";
 import { TabLink, Tabs, TabsList } from "components/Tabs/Tabs";
 import type { FC } from "react";
-import { useSearchParams } from "react-router-dom";
 import { IdpGroupSyncForm } from "./IdpGroupSyncForm";
 import { IdpRoleSyncForm } from "./IdpRoleSyncForm";
 
 interface IdpSyncPageViewProps {
+	tab: string;
 	groupSyncSettings: GroupSyncSettings | undefined;
 	roleSyncSettings: RoleSyncSettings | undefined;
+	claimFieldValues: readonly string[] | undefined;
 	groups: Group[] | undefined;
 	groupsMap: Map<string, string>;
 	roles: Role[] | undefined;
@@ -26,8 +27,10 @@ interface IdpSyncPageViewProps {
 }
 
 export const IdpSyncPageView: FC<IdpSyncPageViewProps> = ({
+	tab,
 	groupSyncSettings,
 	roleSyncSettings,
+	claimFieldValues,
 	groups,
 	groupsMap,
 	roles,
@@ -36,8 +39,6 @@ export const IdpSyncPageView: FC<IdpSyncPageViewProps> = ({
 	onSubmitGroupSyncSettings,
 	onSubmitRoleSyncSettings,
 }) => {
-	const [searchParams] = useSearchParams();
-	const tab = searchParams.get("tab") || "groups";
 	const groupMappingCount = groupSyncSettings?.mapping
 		? Object.entries(groupSyncSettings.mapping).length
 		: 0;
@@ -68,6 +69,7 @@ export const IdpSyncPageView: FC<IdpSyncPageViewProps> = ({
 			{tab === "groups" ? (
 				<IdpGroupSyncForm
 					groupSyncSettings={groupSyncSettings}
+					claimFieldValues={claimFieldValues}
 					groupMappingCount={groupMappingCount}
 					legacyGroupMappingCount={legacyGroupMappingCount}
 					groups={groups}
@@ -78,6 +80,7 @@ export const IdpSyncPageView: FC<IdpSyncPageViewProps> = ({
 			) : (
 				<IdpRoleSyncForm
 					roleSyncSettings={roleSyncSettings}
+					claimFieldValues={claimFieldValues}
 					roleMappingCount={roleMappingCount}
 					roles={roles || []}
 					organization={organization}
diff --git a/site/src/testHelpers/entities.ts b/site/src/testHelpers/entities.ts
index d8ce878bdef6e..ee2158394c7eb 100644
--- a/site/src/testHelpers/entities.ts
+++ b/site/src/testHelpers/entities.ts
@@ -2668,14 +2668,14 @@ export const MockGroupSyncSettings: TypesGen.GroupSyncSettings = {
 	auto_create_missing_groups: false,
 };
 
-export const MockLegacyMappingGroupSyncSettings: TypesGen.GroupSyncSettings = {
+export const MockLegacyMappingGroupSyncSettings = {
 	...MockGroupSyncSettings,
 	mapping: {},
 	legacy_group_name_mapping: {
 		"idp-group-1": "fbd2116a-8961-4954-87ae-e4575bd29ce0",
 		"idp-group-2": "13de3eb4-9b4f-49e7-b0f8-0c3728a0d2e2",
 	},
-};
+} satisfies TypesGen.GroupSyncSettings;
 
 export const MockGroupSyncSettings2: TypesGen.GroupSyncSettings = {
 	field: "group-test",