diff --git a/site/src/pages/AgentsPage/components/ChatConversation/ConversationTimeline.stories.tsx b/site/src/pages/AgentsPage/components/ChatConversation/ConversationTimeline.stories.tsx
index 4c2f7072722..08cd95a8738 100644
--- a/site/src/pages/AgentsPage/components/ChatConversation/ConversationTimeline.stories.tsx
+++ b/site/src/pages/AgentsPage/components/ChatConversation/ConversationTimeline.stories.tsx
@@ -1062,6 +1062,79 @@ export const UserMessageWithMixedAttachments: Story = {
 	},
 };
 
+export const UserMessageLinksStayLiteralAndSafe: Story = {
+	args: {
+		...buildStoryArgs(
+			buildUserMessage({
+				text: "Visit https://coder.com, www.coder.com, see https://coder.com/docs. Literal [docs](https://coder.com/docs) <script>alert(1)</script>",
+			}),
+		),
+		urlTransform: fn((url) =>
+			url === "https://coder.com" ? "https://proxy.example" : url,
+		),
+	},
+	play: async ({ args, canvasElement }) => {
+		const canvas = within(canvasElement);
+		expect(args.urlTransform).toHaveBeenCalled();
+		const secureLink = canvas.getByRole("link", { name: "https://coder.com" });
+		expect(secureLink).toHaveAttribute("href", "https://proxy.example");
+		expect(secureLink).toHaveAttribute("target", "_blank");
+		expect(secureLink).toHaveAttribute(
+			"rel",
+			expect.stringContaining("noopener"),
+		);
+		expect(secureLink).toHaveAttribute(
+			"rel",
+			expect.stringContaining("noreferrer"),
+		);
+
+		expect(canvas.getByRole("link", { name: "www.coder.com" })).toHaveAttribute(
+			"href",
+			"https://www.coder.com",
+		);
+		const docsLinks = canvas.getAllByRole("link", {
+			name: "https://coder.com/docs",
+		});
+		expect(docsLinks).toHaveLength(2);
+		for (const link of docsLinks) {
+			expect(link).toHaveAttribute("href", "https://coder.com/docs");
+		}
+
+		const userRow = secureLink.closest('[data-role="user"]');
+		expect(userRow).not.toBeNull();
+		expect(userRow).toHaveTextContent("see https://coder.com/docs.");
+		expect(userRow).toHaveTextContent("[docs](https://coder.com/docs)");
+		expect(userRow).toHaveTextContent("<script>alert(1)</script>");
+		expect(userRow?.querySelector("script")).toBeNull();
+	},
+};
+
+export const AssistantMessageBareURLIsLinked: Story = {
+	args: {
+		...defaultArgs,
+		parsedMessages: buildMessages([
+			{
+				...baseMessage,
+				id: 1,
+				role: "assistant",
+				content: [
+					{
+						type: "text",
+						text: "Read more at https://coder.com/docs",
+					},
+				],
+			},
+		]),
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		const link = canvas.getByRole("link", { name: "https://coder.com/docs" });
+		expect(link).toHaveAttribute("href", "https://coder.com/docs");
+		expect(link).toHaveAttribute("target", "_blank");
+		expect(link).toHaveAttribute("rel", expect.stringContaining("noopener"));
+	},
+};
+
 /** Text-only messages must not produce spurious image thumbnails. */
 export const UserMessageTextOnly: Story = {
 	args: {
@@ -1200,6 +1273,38 @@ export const UserMessageWithImagesAndFileRefs: Story = {
 	},
 };
 
+export const UserMessageLinkWithInlineFileRef: Story = {
+	args: {
+		...defaultArgs,
+		parsedMessages: buildMessages([
+			{
+				...baseMessage,
+				id: 1,
+				role: "user",
+				content: [
+					{ type: "text", text: "Review https://coder.com/docs with " },
+					{
+						type: "file-reference",
+						file_name: "site/src/components/Button.tsx",
+						start_line: 42,
+						end_line: 42,
+						content: "export const Button = ...",
+					},
+					{ type: "text", text: " before shipping." },
+				],
+			},
+		]),
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		expect(
+			canvas.getByRole("link", { name: "https://coder.com/docs" }),
+		).toHaveAttribute("href", "https://coder.com/docs");
+		expect(canvas.getByText(/Button\.tsx/)).toBeInTheDocument();
+		expect(canvas.getByText(/before shipping/)).toBeInTheDocument();
+	},
+};
+
 /** File references render inline with text, matching the chat input style. */
 export const UserMessageWithInlineFileRef: Story = {
 	args: {
diff --git a/site/src/pages/AgentsPage/components/ChatConversation/ConversationTimeline.tsx b/site/src/pages/AgentsPage/components/ChatConversation/ConversationTimeline.tsx
index fa74ec3b7e7..526049ef5d8 100644
--- a/site/src/pages/AgentsPage/components/ChatConversation/ConversationTimeline.tsx
+++ b/site/src/pages/AgentsPage/components/ChatConversation/ConversationTimeline.tsx
@@ -610,6 +610,7 @@ const ChatMessageItem = memo<{
 							markdown={parsed.markdown}
 							isEditing={editingMessageId === message.id}
 							fadeFromBottom={fadeFromBottom}
+							urlTransform={urlTransform}
 							onImageClick={setPreviewImage}
 							onTextFileClick={setPreviewText}
 						/>
@@ -778,6 +779,7 @@ const StickyUserMessage = memo<{
 	prevUserMessageId?: number;
 	nextUserMessageId?: number;
 	onJumpToUserMessage?: (messageId: number) => void;
+	urlTransform?: UrlTransform;
 	registerSentinel?: (messageId: number, el: HTMLDivElement | null) => void;
 }>(
 	({
@@ -789,6 +791,7 @@ const StickyUserMessage = memo<{
 		prevUserMessageId,
 		nextUserMessageId,
 		onJumpToUserMessage,
+		urlTransform,
 		registerSentinel,
 	}) => {
 		const [isStuck, setIsStuck] = useState(false);
@@ -1028,6 +1031,7 @@ const StickyUserMessage = memo<{
 							prevUserMessageId={prevUserMessageId}
 							nextUserMessageId={nextUserMessageId}
 							onJumpToUserMessage={onJumpToUserMessage}
+							urlTransform={urlTransform}
 						/>
 					</div>
 
@@ -1073,6 +1077,7 @@ const StickyUserMessage = memo<{
 									prevUserMessageId={prevUserMessageId}
 									nextUserMessageId={nextUserMessageId}
 									onJumpToUserMessage={onJumpToUserMessage}
+									urlTransform={urlTransform}
 									fadeFromBottom
 								/>
 							</div>
@@ -1266,6 +1271,7 @@ export const ConversationTimeline = memo<ConversationTimelineProps>(
 									prevUserMessageId={userNeighborsById.get(message.id)?.prevId}
 									nextUserMessageId={userNeighborsById.get(message.id)?.nextId}
 									onJumpToUserMessage={jumpToUserMessage}
+									urlTransform={urlTransform}
 									registerSentinel={registerSentinel}
 								/>
 							);
diff --git a/site/src/pages/AgentsPage/components/ChatConversation/LinkifiedText.test.ts b/site/src/pages/AgentsPage/components/ChatConversation/LinkifiedText.test.ts
new file mode 100644
index 00000000000..7324ec25c91
--- /dev/null
+++ b/site/src/pages/AgentsPage/components/ChatConversation/LinkifiedText.test.ts
@@ -0,0 +1,137 @@
+import { describe, expect, it } from "vitest";
+import { tokenizeLinkifiedText } from "./LinkifiedText";
+
+describe("tokenizeLinkifiedText", () => {
+	it.each([
+		{
+			name: "links an HTTPS URL in a sentence",
+			text: "Visit https://coder.com/docs for details",
+			expected: [
+				{ type: "text", value: "Visit " },
+				{
+					type: "url",
+					value: "https://coder.com/docs",
+					href: "https://coder.com/docs",
+				},
+				{ type: "text", value: " for details" },
+			],
+		},
+		{
+			name: "links an HTTP URL",
+			text: "http://localhost:3000/path",
+			expected: [
+				{
+					type: "url",
+					value: "http://localhost:3000/path",
+					href: "http://localhost:3000/path",
+				},
+			],
+		},
+		{
+			name: "adds an HTTPS scheme to a www URL",
+			text: "www.coder.com",
+			expected: [
+				{
+					type: "url",
+					value: "www.coder.com",
+					href: "https://www.coder.com",
+				},
+			],
+		},
+		{
+			name: "excludes trailing punctuation",
+			text: "See https://coder.com/docs., and www.coder.com?",
+			expected: [
+				{ type: "text", value: "See " },
+				{
+					type: "url",
+					value: "https://coder.com/docs",
+					href: "https://coder.com/docs",
+				},
+				{ type: "text", value: "., and " },
+				{
+					type: "url",
+					value: "www.coder.com",
+					href: "https://www.coder.com",
+				},
+				{ type: "text", value: "?" },
+			],
+		},
+		{
+			name: "keeps balanced URL parentheses",
+			text: "https://en.wikipedia.org/wiki/Foo_(bar)",
+			expected: [
+				{
+					type: "url",
+					value: "https://en.wikipedia.org/wiki/Foo_(bar)",
+					href: "https://en.wikipedia.org/wiki/Foo_(bar)",
+				},
+			],
+		},
+		{
+			name: "excludes an unmatched trailing parenthesis",
+			text: "(https://coder.com/docs)",
+			expected: [
+				{ type: "text", value: "(" },
+				{
+					type: "url",
+					value: "https://coder.com/docs",
+					href: "https://coder.com/docs",
+				},
+				{ type: "text", value: ")" },
+			],
+		},
+		{
+			name: "links multiple URLs",
+			text: "https://coder.com and www.example.com",
+			expected: [
+				{
+					type: "url",
+					value: "https://coder.com",
+					href: "https://coder.com",
+				},
+				{ type: "text", value: " and " },
+				{
+					type: "url",
+					value: "www.example.com",
+					href: "https://www.example.com",
+				},
+			],
+		},
+		{
+			name: "preserves text without URLs",
+			text: "Keep *markdown* literal",
+			expected: [{ type: "text", value: "Keep *markdown* literal" }],
+		},
+		{
+			name: "preserves newlines in text segments",
+			text: "First line\nhttps://coder.com\nLast line",
+			expected: [
+				{ type: "text", value: "First line\n" },
+				{
+					type: "url",
+					value: "https://coder.com",
+					href: "https://coder.com",
+				},
+				{ type: "text", value: "\nLast line" },
+			],
+		},
+		{
+			name: "does not link a bare domain",
+			text: "Visit coder.com",
+			expected: [{ type: "text", value: "Visit coder.com" }],
+		},
+		{
+			name: "does not link incomplete URL prefixes",
+			text: "Keep https:// and www. literal",
+			expected: [{ type: "text", value: "Keep https:// and www. literal" }],
+		},
+		{
+			name: "handles empty text",
+			text: "",
+			expected: [],
+		},
+	])("$name", ({ text, expected }) => {
+		expect(tokenizeLinkifiedText(text)).toEqual(expected);
+	});
+});
diff --git a/site/src/pages/AgentsPage/components/ChatConversation/LinkifiedText.tsx b/site/src/pages/AgentsPage/components/ChatConversation/LinkifiedText.tsx
new file mode 100644
index 00000000000..90e8dcc6dfa
--- /dev/null
+++ b/site/src/pages/AgentsPage/components/ChatConversation/LinkifiedText.tsx
@@ -0,0 +1,102 @@
+import { type FC, Fragment } from "react";
+import type { UrlTransform } from "streamdown";
+
+const URL_PATTERN =
+	/\b(?:https?:\/\/(?:[a-z0-9]|\[[0-9a-f:]+\])|www\.[a-z0-9])[^\s<>"']*/gi;
+const TRAILING_PUNCTUATION = new Set([".", ",", ";", ":", "!", "?"]);
+
+type LinkifiedTextSegment =
+	| { type: "text"; value: string }
+	| { type: "url"; value: string; href: string };
+
+const trimURLSuffix = (value: string) => {
+	let end = value.length;
+	let openParentheses = 0;
+	let closeParentheses = 0;
+
+	for (const character of value) {
+		if (character === "(") {
+			openParentheses++;
+		} else if (character === ")") {
+			closeParentheses++;
+		}
+	}
+
+	while (end > 0) {
+		const character = value[end - 1];
+		if (TRAILING_PUNCTUATION.has(character)) {
+			end--;
+			continue;
+		}
+		if (character === ")" && closeParentheses > openParentheses) {
+			end--;
+			closeParentheses--;
+			continue;
+		}
+		break;
+	}
+
+	return value.slice(0, end);
+};
+
+/** Splits literal prompt text into text and safe HTTP(S) URL segments. */
+export const tokenizeLinkifiedText = (text: string): LinkifiedTextSegment[] => {
+	const segments: LinkifiedTextSegment[] = [];
+	let cursor = 0;
+
+	for (const match of text.matchAll(URL_PATTERN)) {
+		const index = match.index;
+		const value = trimURLSuffix(match[0]);
+		if (value.length === 0) {
+			continue;
+		}
+
+		if (index > cursor) {
+			segments.push({ type: "text", value: text.slice(cursor, index) });
+		}
+		segments.push({
+			type: "url",
+			value,
+			href: value.toLowerCase().startsWith("www.") ? `https://${value}` : value,
+		});
+		cursor = index + value.length;
+	}
+
+	if (cursor < text.length) {
+		segments.push({ type: "text", value: text.slice(cursor) });
+	}
+
+	return segments;
+};
+
+export const LinkifiedText: FC<{
+	text: string;
+	urlTransform?: UrlTransform;
+}> = ({ text, urlTransform }) => {
+	return tokenizeLinkifiedText(text).map((segment, index) => {
+		if (segment.type === "text") {
+			return <Fragment key={index}>{segment.value}</Fragment>;
+		}
+
+		const href =
+			(urlTransform
+				? urlTransform(segment.href, "href", {
+						type: "element",
+						tagName: "a",
+						properties: { href: segment.href },
+						children: [{ type: "text", value: segment.value }],
+					})
+				: segment.href) ?? segment.href;
+		return (
+			<a
+				key={index}
+				href={href}
+				target="_blank"
+				rel="noopener noreferrer"
+				className="text-content-link no-underline hover:underline hover:decoration-content-link"
+			>
+				{segment.value}
+			</a>
+		);
+	});
+};
diff --git a/site/src/pages/AgentsPage/components/ChatConversation/UserMessageContent.tsx b/site/src/pages/AgentsPage/components/ChatConversation/UserMessageContent.tsx
index 7443d88b41a..98528ca9f7d 100644
--- a/site/src/pages/AgentsPage/components/ChatConversation/UserMessageContent.tsx
+++ b/site/src/pages/AgentsPage/components/ChatConversation/UserMessageContent.tsx
@@ -1,4 +1,5 @@
-import { type FC, Fragment } from "react";
+import type { FC } from "react";
+import type { UrlTransform } from "streamdown";
 import { cn } from "#/utils/cn";
 import { Message, MessageContent } from "../ChatElements";
 import { FileReferenceChip } from "../ChatMessageInput/FileReferenceChip";
@@ -11,6 +12,7 @@ import {
 	AttachmentBlock,
 	type PreviewTextAttachment,
 } from "./AttachmentBlocks";
+import { LinkifiedText } from "./LinkifiedText";
 import type {
 	MessageDisplayState,
 	UserInlineRenderBlock,
@@ -31,9 +33,16 @@ const renderUserInlineBlock = (
 	inlineParts: readonly InlinePart[],
 	block: UserInlineRenderBlock,
 	index: number,
+	urlTransform?: UrlTransform,
 ) => {
 	if (block.type === "response") {
-		return <Fragment key={index}>{block.text}</Fragment>;
+		return (
+			<LinkifiedText
+				key={index}
+				text={block.text}
+				urlTransform={urlTransform}
+			/>
+		);
 	}
 
 	return (
@@ -50,10 +59,13 @@ const renderUserInlineBlock = (
 	);
 };
 
-const renderUserInlineContent = (blocks: readonly UserInlineRenderBlock[]) => {
+const renderUserInlineContent = (
+	blocks: readonly UserInlineRenderBlock[],
+	urlTransform?: UrlTransform,
+) => {
 	const inlineParts = getInlineParts(blocks);
 	return blocks.map((block, index) =>
-		renderUserInlineBlock(inlineParts, block, index),
+		renderUserInlineBlock(inlineParts, block, index, urlTransform),
 	);
 };
 
@@ -62,6 +74,7 @@ export const UserMessageContent: FC<{
 	markdown: string;
 	isEditing?: boolean;
 	fadeFromBottom?: boolean;
+	urlTransform?: UrlTransform;
 	onImageClick?: (src: string) => void;
 	onTextFileClick?: (attachment: PreviewTextAttachment) => void;
 }> = ({
@@ -69,6 +82,7 @@ export const UserMessageContent: FC<{
 	markdown,
 	isEditing = false,
 	fadeFromBottom = false,
+	urlTransform,
 	onImageClick,
 	onTextFileClick,
 }) => {
@@ -90,9 +104,17 @@ export const UserMessageContent: FC<{
 						<div className="flex items-start gap-2">
 							{displayState.hasUserMessageBody && (
 								<span className="min-w-0 flex-1">
-									{displayState.userInlineContent.length > 0
-										? renderUserInlineContent(displayState.userInlineContent)
-										: markdown || ""}
+									{displayState.userInlineContent.length > 0 ? (
+										renderUserInlineContent(
+											displayState.userInlineContent,
+											urlTransform,
+										)
+									) : (
+										<LinkifiedText
+											text={markdown || ""}
+											urlTransform={urlTransform}
+										/>
+									)}
 								</span>
 							)}
 						</div>