diff --git a/site/src/api/queries/chats.ts b/site/src/api/queries/chats.ts
index 0da5ec2197..9525f3a1c2 100644
--- a/site/src/api/queries/chats.ts
+++ b/site/src/api/queries/chats.ts
@@ -1743,7 +1743,9 @@ export const deleteUserChatProviderKey = (queryClient: QueryClient) => ({
 	},
 });
 
-const invalidateChatConfigurationQueries = async (queryClient: QueryClient) => {
+export const invalidateChatConfigurationQueries = async (
+	queryClient: QueryClient,
+) => {
 	await Promise.all([
 		queryClient.invalidateQueries({ queryKey: chatProviderConfigsKey }),
 		queryClient.invalidateQueries({ queryKey: chatModelConfigsKey }),
diff --git a/site/src/pages/AISettingsPage/ProvidersPage/UpdateProviderPage/UpdateProviderPageView.tsx b/site/src/pages/AISettingsPage/ProvidersPage/UpdateProviderPage/UpdateProviderPageView.tsx
index dbeb16003d..e0290652cc 100644
--- a/site/src/pages/AISettingsPage/ProvidersPage/UpdateProviderPage/UpdateProviderPageView.tsx
+++ b/site/src/pages/AISettingsPage/ProvidersPage/UpdateProviderPage/UpdateProviderPageView.tsx
@@ -4,18 +4,31 @@ import { useState } from "react";
 import { useMutation, useQuery, useQueryClient } from "react-query";
 import { Link, Navigate, useNavigate, useParams } from "react-router";
 import { toast } from "sonner";
+import { API } from "#/api/api";
 import { getErrorMessage } from "#/api/errors";
 import {
 	aiProvider,
 	deleteAIProviderMutation,
 	updateAIProviderMutation,
 } from "#/api/queries/aiProviders";
+import {
+	chatModelConfigs,
+	invalidateChatConfigurationQueries,
+} from "#/api/queries/chats";
 import { Avatar } from "#/components/Avatar/Avatar";
 import { Badge } from "#/components/Badge/Badge";
 import { Button } from "#/components/Button/Button";
-import { DeleteDialog } from "#/components/Dialogs/DeleteDialog/DeleteDialog";
+import {
+	Dialog,
+	DialogContent,
+	DialogFooter,
+	DialogHeader,
+	DialogTitle,
+} from "#/components/Dialog/Dialog";
+import { Input } from "#/components/Input/Input";
 import { Loader } from "#/components/Loader/Loader";
 import { SettingsHeaderTitle } from "#/components/SettingsHeader/SettingsHeader";
+import { Spinner } from "#/components/Spinner/Spinner";
 import { Switch } from "#/components/Switch/Switch";
 import { pageTitle } from "#/utils/page";
 import { ProviderForm } from "../components/ProviderForm";
@@ -36,6 +49,8 @@ const UpdateProviderPageView: React.FC = () => {
 	const navigate = useNavigate();
 
 	const [deleteDialogOpen, setDeleteDialogOpen] = useState(false);
+	const [deleteConfirmText, setDeleteConfirmText] = useState("");
+	const [isCascadeDeleting, setIsCascadeDeleting] = useState(false);
 
 	const providerQuery = useQuery({
 		...aiProvider(providerId ?? ""),
@@ -54,6 +69,16 @@ const UpdateProviderPageView: React.FC = () => {
 		deleteAIProviderMutation(queryClient, providerId ?? ""),
 	);
 
+	const modelConfigsQuery = useQuery({
+		...chatModelConfigs(),
+		enabled: Boolean(providerId),
+	});
+
+	const associatedModels = (modelConfigsQuery.data ?? []).filter(
+		(mc) => mc.ai_provider_id === provider?.id,
+	);
+	const associatedModelCount = associatedModels.length;
+
 	// Rendered into every non-redirect return so the document title reflects
 	// the provider as soon as we know it; falls back to a placeholder while
 	// the query is in flight.
@@ -210,36 +235,123 @@ const UpdateProviderPageView: React.FC = () => {
 						}}
 					/>
 				</div>
-				<DeleteDialog
-					key={provider.name}
-					isOpen={deleteDialogOpen}
-					title="Delete provider"
-					entity="provider"
-					name={provider.name}
-					confirmLoading={deleteMutation.isPending}
-					onCancel={() => {
-						setDeleteDialogOpen(false);
+				<Dialog
+					open={deleteDialogOpen}
+					onOpenChange={(open) => {
+						if (!open && !isCascadeDeleting && !deleteMutation.isPending) {
+							setDeleteDialogOpen(false);
+							setDeleteConfirmText("");
+						}
 					}}
-					onConfirm={() => {
-						deleteMutation.mutate(undefined, {
-							onSuccess: () => {
-								toast.success(
-									`Provider "${provider.display_name || provider.name}" deleted.`,
-								);
-								setDeleteDialogOpen(false);
-								void navigate(BACK_HREF, { replace: true });
-							},
-							onError: (error) => {
-								toast.error(
-									getErrorMessage(
-										error,
-										`Failed to delete provider "${provider.display_name || provider.name}".`,
-									),
-								);
-							},
-						});
-					}}
-				/>
+				>
+					<DialogContent variant="destructive">
+						<DialogHeader>
+							<DialogTitle>Delete provider</DialogTitle>
+						</DialogHeader>
+						<div className="flex flex-col gap-3 text-sm text-content-secondary">
+							<p className="m-0 font-medium text-content-destructive">
+								Deleting this provider is irreversible!
+							</p>
+							{associatedModelCount > 0 && (
+								<ul className="m-0 pl-5">
+									<li>
+										Deleting this provider will also disable{" "}
+										<strong className="text-content-primary">
+											{associatedModelCount}{" "}
+											{associatedModelCount === 1 ? "model" : "models"}
+										</strong>{" "}
+										from your settings.
+									</li>
+								</ul>
+							)}
+							<p className="m-0">
+								Type{" "}
+								<strong className="text-content-primary">
+									{provider.name}
+								</strong>{" "}
+								to confirm.
+							</p>
+							<Input
+								id="delete-confirm"
+								aria-label={`Type ${provider.name} to confirm`}
+								autoFocus
+								autoComplete="off"
+								placeholder={provider.name}
+								value={deleteConfirmText}
+								onChange={(e) => setDeleteConfirmText(e.target.value)}
+							/>
+						</div>
+						<DialogFooter>
+							<Button
+								variant="outline"
+								onClick={() => {
+									setDeleteDialogOpen(false);
+									setDeleteConfirmText("");
+								}}
+								disabled={isCascadeDeleting || deleteMutation.isPending}
+							>
+								Cancel
+							</Button>
+							<Button
+								variant="destructive"
+								className="disabled:border-border"
+								disabled={
+									deleteConfirmText !== provider.name ||
+									isCascadeDeleting ||
+									deleteMutation.isPending ||
+									modelConfigsQuery.isLoading ||
+									modelConfigsQuery.isError
+								}
+								onClick={() => {
+									const deleteAll = async () => {
+										setIsCascadeDeleting(true);
+										try {
+											for (const mc of associatedModels) {
+												await API.experimental.updateChatModelConfig(mc.id, {
+													enabled: false,
+												});
+											}
+											await invalidateChatConfigurationQueries(queryClient);
+											deleteMutation.mutate(undefined, {
+												onSuccess: () => {
+													toast.success(
+														`Provider "${provider.display_name || provider.name}" deleted.`,
+													);
+													setDeleteDialogOpen(false);
+													setDeleteConfirmText("");
+													void navigate(BACK_HREF, { replace: true });
+												},
+												onError: (error) => {
+													toast.error(
+														getErrorMessage(
+															error,
+															`Failed to delete provider "${provider.display_name || provider.name}".`,
+														),
+													);
+												},
+												onSettled: () => {
+													setIsCascadeDeleting(false);
+												},
+											});
+										} catch (error) {
+											toast.error(
+												getErrorMessage(error, "Failed to delete provider."),
+											);
+											setIsCascadeDeleting(false);
+											await invalidateChatConfigurationQueries(queryClient);
+										}
+									};
+									void deleteAll();
+								}}
+							>
+								{(isCascadeDeleting || deleteMutation.isPending) && (
+									<Spinner className="h-4 w-4" loading />
+								)}
+								Delete provider
+							</Button>
+						</DialogFooter>
+					</DialogContent>
+				</Dialog>
 			</div>
 		</>
 	);
diff --git a/site/src/pages/AISettingsPage/ProvidersPage/components/ProviderForm.tsx b/site/src/pages/AISettingsPage/ProvidersPage/components/ProviderForm.tsx
index 0a609de2ac..ae1d886508 100644
--- a/site/src/pages/AISettingsPage/ProvidersPage/components/ProviderForm.tsx
+++ b/site/src/pages/AISettingsPage/ProvidersPage/components/ProviderForm.tsx
@@ -303,7 +303,7 @@ export const ProviderForm: FC<ProviderFormProps> = ({
 								required
 								field={getFieldHelpers("name")}
 								label="Name"
-								description="Unique identifier (used in urls, can't be changed)"
+								description="URL identifier. Cannot be changed."
 								className="w-full"
 								placeholder={namePlaceholder(form.values.type)}
 								disabled={editing}
@@ -341,7 +341,7 @@ export const ProviderForm: FC<ProviderFormProps> = ({
 								required
 								field={getFieldHelpers("name")}
 								label="Name"
-								description="Unique identifier (used in urls, can't be changed)"
+								description="URL identifier. Cannot be changed."
 								className="w-full"
 								placeholder={namePlaceholder(form.values.type)}
 								disabled={editing}
diff --git a/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ChatModelAdminPanel.tsx b/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ChatModelAdminPanel.tsx
index 6ecb1b0cc9..ea84ab77e7 100644
--- a/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ChatModelAdminPanel.tsx
+++ b/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ChatModelAdminPanel.tsx
@@ -324,6 +324,7 @@ export const ChatModelAdminPanel: FC<ChatModelAdminPanelProps> = ({
 						onCreateProvider={onCreateProvider}
 						onUpdateProvider={onUpdateProvider}
 						onDeleteProvider={onDeleteProvider}
+						onDisableModel={onUpdateModel}
 					/>
 				) : (
 					<ModelsSection
diff --git a/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ModelsSection.tsx b/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ModelsSection.tsx
index 0cc2a554d5..bf105a1ecb 100644
--- a/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ModelsSection.tsx
+++ b/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ModelsSection.tsx
@@ -377,7 +377,7 @@ export const ModelsSection: FC<ModelsSectionProps> = ({
 										)}
 									</div>
 									{modelConfig.enabled === false && (
-										<Badge size="xs" variant="warning">
+										<Badge size="xs" variant="default">
 											disabled
 										</Badge>
 									)}
diff --git a/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ProviderForm.tsx b/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ProviderForm.tsx
index fe817705f7..ed6c0fc474 100644
--- a/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ProviderForm.tsx
+++ b/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ProviderForm.tsx
@@ -8,6 +8,8 @@ import {
 	useState,
 } from "react";
 import { useNavigate } from "react-router";
+import { toast } from "sonner";
+import { getErrorMessage } from "#/api/errors";
 import type * as TypesGen from "#/api/typesGenerated";
 import { Alert, AlertDescription, AlertTitle } from "#/components/Alert/Alert";
 import { Button } from "#/components/Button/Button";
@@ -45,6 +47,10 @@ interface ProviderFormProps {
 		req: TypesGen.UpdateChatProviderConfigRequest,
 	) => Promise<unknown>;
 	onDeleteProvider: (providerConfigId: string) => Promise<void>;
+	onDisableModel: (
+		modelConfigId: string,
+		req: TypesGen.UpdateChatModelConfigRequest,
+	) => Promise<unknown>;
 	onBack: () => void;
 }
 
@@ -55,6 +61,7 @@ export const ProviderForm: FC<ProviderFormProps> = ({
 	onCreateProvider,
 	onUpdateProvider,
 	onDeleteProvider,
+	onDisableModel,
 	onBack,
 }) => {
 	const navigate = useNavigate();
@@ -80,6 +87,7 @@ export const ProviderForm: FC<ProviderFormProps> = ({
 	const [apiKeyModified, setApiKeyModified] = useState(false);
 	const [baseURLValue, setBaseURLValue] = useState(initialValues.baseURL);
 	const [confirmingDelete, setConfirmingDelete] = useState(false);
+	const [isCascadeDeleting, setIsCascadeDeleting] = useState(false);
 
 	const isBedrockProvider = provider === "bedrock";
 	const isAPIKeyEnvManaged = isEnvPreset && !providerConfig;
@@ -106,10 +114,11 @@ export const ProviderForm: FC<ProviderFormProps> = ({
 		? "Bedrock runtime endpoint. Use the AWS region for the models this provider should call."
 		: "Endpoint used to call this provider.";
 	const apiKeyPlaceholder = isBedrockProvider ? "Enter bearer token" : "sk-...";
+	const associatedModelCount = providerState.modelConfigs.length;
 	const deleteProviderDescription =
-		"Are you sure you want to delete this provider? The provider will be " +
-		"disabled and hidden from new model configuration. Existing model " +
-		"configs that reference it remain saved but cannot run until updated.";
+		associatedModelCount > 0
+			? `Deleting this provider will also disable ${associatedModelCount} ${associatedModelCount === 1 ? "model" : "models"} from your settings.`
+			: "Are you sure you want to delete this provider? This action is irreversible.";
 	const hasNewProviderConfiguration = !providerConfig;
 
 	const isDirty =
@@ -371,10 +380,29 @@ export const ProviderForm: FC<ProviderFormProps> = ({
 				<ConfirmDeleteDialog
 					entity="provider"
 					description={deleteProviderDescription}
-					onConfirm={() => void onDeleteProvider(providerConfig.id)}
-					isPending={isProviderMutationPending}
+					onConfirm={() => {
+						setIsCascadeDeleting(true);
+						const chain = providerState.modelConfigs.reduce<Promise<unknown>>(
+							(prev, mc) =>
+								prev.then(() => onDisableModel(mc.id, { enabled: false })),
+							Promise.resolve(),
+						);
+						chain
+							.then(() => onDeleteProvider(providerConfig.id))
+							.catch((error: unknown) => {
+								toast.error(
+									getErrorMessage(error, "Failed to delete provider."),
+								);
+							})
+							.then(() => setIsCascadeDeleting(false));
+					}}
+					isPending={isCascadeDeleting || isProviderMutationPending}
 					open={confirmingDelete}
-					onOpenChange={(open) => !open && setConfirmingDelete(false)}
+					onOpenChange={(open) => {
+						if (!open && !isCascadeDeleting && !isProviderMutationPending) {
+							setConfirmingDelete(false);
+						}
+					}}
 				/>
 			)}
 		</div>
diff --git a/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ProvidersSection.tsx b/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ProvidersSection.tsx
index 56b3d293bf..eb0a68827c 100644
--- a/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ProvidersSection.tsx
+++ b/site/src/pages/AgentsPage/components/ChatModelAdminPanel/ProvidersSection.tsx
@@ -10,6 +10,7 @@ import {
 	type AIProviderType,
 	AIProviderTypes,
 	type CreateChatProviderConfigRequest,
+	type UpdateChatModelConfigRequest,
 	type UpdateChatProviderConfigRequest,
 } from "#/api/typesGenerated";
 import { Badge } from "#/components/Badge/Badge";
@@ -79,6 +80,10 @@ interface ProvidersSectionProps {
 		req: UpdateChatProviderConfigRequest,
 	) => Promise<unknown>;
 	onDeleteProvider: (providerConfigId: string) => Promise<void>;
+	onDisableModel: (
+		modelConfigId: string,
+		req: UpdateChatModelConfigRequest,
+	) => Promise<unknown>;
 }
 
 export const ProvidersSection: FC<ProvidersSectionProps> = ({
@@ -90,6 +95,7 @@ export const ProvidersSection: FC<ProvidersSectionProps> = ({
 	onCreateProvider,
 	onUpdateProvider,
 	onDeleteProvider,
+	onDisableModel,
 }) => {
 	const [searchParams, setSearchParams] = useSearchParams();
 	const navigate = useNavigate();
@@ -198,6 +204,7 @@ export const ProvidersSection: FC<ProvidersSectionProps> = ({
 					}
 				}}
 				onBack={clearProviderView}
+				onDisableModel={onDisableModel}
 			/>
 		);
 	}