diff --git a/ui/admin/app/components/chat/Message.tsx b/ui/admin/app/components/chat/Message.tsx
index 3708c513e..a4b925875 100644
--- a/ui/admin/app/components/chat/Message.tsx
+++ b/ui/admin/app/components/chat/Message.tsx
@@ -1,21 +1,34 @@
 import "@radix-ui/react-tooltip";
 import { WrenchIcon } from "lucide-react";
-import React, { useMemo } from "react";
+import React, { useMemo, useState } from "react";
+import { useForm } from "react-hook-form";
 import Markdown, { defaultUrlTransform } from "react-markdown";
 import rehypeExternalLinks from "rehype-external-links";
 import remarkGfm from "remark-gfm";
 
-import { OAuthPrompt } from "~/lib/model/chatEvents";
+import { AuthPrompt } from "~/lib/model/chatEvents";
 import { Message as MessageType } from "~/lib/model/messages";
+import { PromptApiService } from "~/lib/service/api/PromptApi";
 import { cn } from "~/lib/utils";
 
 import { TypographyP } from "~/components/Typography";
 import { MessageDebug } from "~/components/chat/MessageDebug";
 import { ToolCallInfo } from "~/components/chat/ToolCallInfo";
+import { ControlledInput } from "~/components/form/controlledInputs";
 import { CustomMarkdownComponents } from "~/components/react-markdown";
 import { ToolIcon } from "~/components/tools/ToolIcon";
 import { Button } from "~/components/ui/button";
 import { Card } from "~/components/ui/card";
+import {
+    Dialog,
+    DialogContent,
+    DialogHeader,
+    DialogTitle,
+    DialogTrigger,
+} from "~/components/ui/dialog";
+import { Form } from "~/components/ui/form";
+import { Link } from "~/components/ui/link";
+import { useAsync } from "~/hooks/useAsync";
 
 interface MessageProps {
     message: MessageType;
@@ -126,7 +139,9 @@ export const Message = React.memo(({ message }: MessageProps) => {
 
 Message.displayName = "Message";
 
-function PromptMessage({ prompt }: { prompt: OAuthPrompt }) {
+function PromptMessage({ prompt }: { prompt: AuthPrompt }) {
+    const [open, setOpen] = useState(false);
+
     if (!prompt.metadata) return null;
 
     return (
@@ -141,23 +156,107 @@ function PromptMessage({ prompt }: { prompt: OAuthPrompt }) {
                 Tool Call requires authentication
             </TypographyP>
 
-            <Button asChild variant="secondary">
-                <a
+            {prompt.metadata.authType === "oauth" && (
+                <Link
+                    buttonVariant="secondary"
+                    as="button"
                     rel="noreferrer"
                     target="_blank"
-                    href={prompt.metadata?.authURL}
-                    className="flex items-center gap-2 w-fit"
+                    to={prompt.metadata.authURL}
+                    className="w-fit"
                 >
                     <ToolIcon
-                        icon={prompt.metadata?.icon}
-                        category={prompt.metadata?.category}
+                        icon={prompt.metadata.icon}
+                        category={prompt.metadata.category}
                         name={prompt.name}
-                        className="w-5 h-5"
                         disableTooltip
                     />
-                    Authenticate with {prompt.metadata?.category}
-                </a>
-            </Button>
+                    Authenticate with {prompt.metadata.category}
+                </Link>
+            )}
+
+            {prompt.metadata.authType === "basic" && prompt.fields && (
+                <Dialog open={open} onOpenChange={setOpen}>
+                    <DialogTrigger asChild>
+                        <Button
+                            variant="secondary"
+                            startContent={
+                                <ToolIcon
+                                    icon={prompt.metadata.icon}
+                                    category={prompt.metadata.category}
+                                    name={prompt.name}
+                                    disableTooltip
+                                />
+                            }
+                        >
+                            Authenticate with {prompt.metadata.category}
+                        </Button>
+                    </DialogTrigger>
+
+                    <DialogContent>
+                        <DialogHeader>
+                            <DialogTitle>
+                                Authenticate with {prompt.metadata.category}
+                            </DialogTitle>
+                        </DialogHeader>
+
+                        <PromptAuthForm
+                            prompt={prompt}
+                            onSuccess={() => setOpen(false)}
+                        />
+                    </DialogContent>
+                </Dialog>
+            )}
         </div>
     );
 }
+
+function PromptAuthForm({
+    prompt,
+    onSuccess,
+}: {
+    prompt: AuthPrompt;
+    onSuccess: () => void;
+}) {
+    const authenticate = useAsync(PromptApiService.promptResponse, {
+        onSuccess,
+    });
+
+    const form = useForm<Record<string, string>>({
+        defaultValues: prompt.fields?.reduce(
+            (acc, field) => {
+                acc[field] = "";
+                return acc;
+            },
+            {} as Record<string, string>
+        ),
+    });
+
+    const handleSubmit = form.handleSubmit(async (values) =>
+        authenticate.execute({ id: prompt.id, response: values })
+    );
+
+    return (
+        <Form {...form}>
+            <form onSubmit={handleSubmit} className="flex flex-col gap-4">
+                {prompt.fields?.map((field) => (
+                    <ControlledInput
+                        key={field}
+                        control={form.control}
+                        name={field}
+                        label={field}
+                        type={field.includes("password") ? "password" : "text"}
+                    />
+                ))}
+
+                <Button
+                    disabled={authenticate.isLoading}
+                    loading={authenticate.isLoading}
+                    type="submit"
+                >
+                    Authenticate
+                </Button>
+            </form>
+        </Form>
+    );
+}
diff --git a/ui/admin/app/lib/model/chatEvents.ts b/ui/admin/app/lib/model/chatEvents.ts
index 189bad3da..2ac485d7c 100644
--- a/ui/admin/app/lib/model/chatEvents.ts
+++ b/ui/admin/app/lib/model/chatEvents.ts
@@ -13,23 +13,30 @@ export type ToolCall = {
     };
 };
 
-type PromptOAuthMeta = {
-    authType: "oauth";
-    authURL: string;
+type PromptAuthMetaBase = {
     category: string;
     icon: string;
     toolContext: string;
     toolDisplayName: string;
 };
 
-export type OAuthPrompt = {
+type PromptOAuthMeta = PromptAuthMetaBase & {
+    authType: "oauth";
+    authURL: string;
+};
+
+type PromptAuthBasicMeta = PromptAuthMetaBase & {
+    authType: "basic";
+};
+
+export type AuthPrompt = {
     id?: string;
     name: string;
     time?: Date;
     message: string;
     fields?: string[];
     sensitive?: boolean;
-    metadata?: PromptOAuthMeta;
+    metadata?: PromptOAuthMeta | PromptAuthBasicMeta;
 };
 
 // note(ryanhopperlowe) renaming this to ChatEvent to differentiate itself specifically for a chat with an agent
@@ -45,7 +52,7 @@ export type ChatEvent = {
     waitingOnModel?: boolean;
     toolInput?: ToolInput;
     toolCall?: ToolCall;
-    prompt?: OAuthPrompt;
+    prompt?: AuthPrompt;
 };
 
 export function combineChatEvents(events: ChatEvent[]): ChatEvent[] {
diff --git a/ui/admin/app/lib/model/messages.ts b/ui/admin/app/lib/model/messages.ts
index d7813b86e..72c5c6880 100644
--- a/ui/admin/app/lib/model/messages.ts
+++ b/ui/admin/app/lib/model/messages.ts
@@ -1,4 +1,4 @@
-import { ChatEvent, OAuthPrompt, ToolCall } from "~/lib/model/chatEvents";
+import { AuthPrompt, ChatEvent, ToolCall } from "~/lib/model/chatEvents";
 import { Run } from "~/lib/model/runs";
 
 export interface Message {
@@ -6,7 +6,7 @@ export interface Message {
     sender: "user" | "agent";
     // note(ryanhopperlowe) we only support one tool call per message for now
     // leaving it as an array case that changes in the future
-    prompt?: OAuthPrompt;
+    prompt?: AuthPrompt;
     tools?: ToolCall[];
     runId?: string;
     isLoading?: boolean;
@@ -40,7 +40,7 @@ export const toolCallMessage = (toolCall: ToolCall): Message => ({
     tools: [toolCall],
 });
 
-export const promptMessage = (prompt: OAuthPrompt, runID: string): Message => ({
+export const promptMessage = (prompt: AuthPrompt, runID: string): Message => ({
     sender: "agent",
     text: prompt.message,
     prompt,
diff --git a/ui/admin/app/lib/routers/apiRoutes.ts b/ui/admin/app/lib/routers/apiRoutes.ts
index 4951a4f77..947be4c58 100644
--- a/ui/admin/app/lib/routers/apiRoutes.ts
+++ b/ui/admin/app/lib/routers/apiRoutes.ts
@@ -127,6 +127,10 @@ export const ApiRoutes = {
             buildUrl(`/threads/${threadId}/knowledge`),
         getFiles: (threadId: string) => buildUrl(`/threads/${threadId}/files`),
     },
+    prompt: {
+        base: () => buildUrl("/prompt"),
+        promptResponse: () => buildUrl("/prompt"),
+    },
     runs: {
         base: () => buildUrl("/runs"),
         getRunById: (runId: string) => buildUrl(`/runs/${runId}`),
diff --git a/ui/admin/app/lib/service/api/PromptApi.tsx b/ui/admin/app/lib/service/api/PromptApi.tsx
new file mode 100644
index 000000000..d8db2cce7
--- /dev/null
+++ b/ui/admin/app/lib/service/api/PromptApi.tsx
@@ -0,0 +1,14 @@
+import { ApiRoutes } from "~/lib/routers/apiRoutes";
+import { request } from "~/lib/service/api/primitives";
+
+async function promptResponse(prompt: {
+    id?: string;
+    response?: Record<string, string>;
+}) {
+    await request({
+        method: "POST",
+        url: ApiRoutes.prompt.promptResponse().url,
+        data: prompt,
+    });
+}
+export const PromptApiService = { promptResponse };