diff --git a/webview-ui/src/components/chat/TaskHeader.tsx b/webview-ui/src/components/chat/TaskHeader.tsx
index 0941a22e2b..b614dbbb92 100644
--- a/webview-ui/src/components/chat/TaskHeader.tsx
+++ b/webview-ui/src/components/chat/TaskHeader.tsx
@@ -29,6 +29,8 @@ import { Mention } from "./Mention"
 import { TodoListDisplay } from "./TodoListDisplay"
 import { LucideIconButton } from "./LucideIconButton"
 
+import MarkdownBlock from "../common/MarkdownBlock"
+
 export interface TaskHeaderProps {
 	task: ClineMessage
 	tokensIn: number
@@ -163,7 +165,9 @@ const TaskHeader = ({
 							e.target.closest('[role="button"]') ||
 							e.target.closest("[data-radix-popper-content-wrapper]") ||
 							e.target.closest("img") ||
-							e.target.tagName === "IMG")
+							e.target.tagName === "IMG" ||
+							e.target.closest("a") ||
+							e.target.tagName === "A")
 					) {
 						return
 					}
@@ -324,13 +328,13 @@ const TaskHeader = ({
 							className="text-vscode-font-size overflow-y-auto break-words break-anywhere relative">
 							<div
 								ref={textRef}
-								className="overflow-auto max-h-80 whitespace-pre-wrap break-words break-anywhere cursor-text py-0.5"
+								className="scrollable overflow-auto max-h-80 break-words break-anywhere cursor-text py-0.5"
 								style={{
 									display: "-webkit-box",
 									WebkitLineClamp: "unset",
 									WebkitBoxOrient: "vertical",
 								}}>
-								<Mention text={task.text} />
+								<MarkdownBlock markdown={task.text ?? ""} />
 							</div>
 						</div>
 						{task.images && task.images.length > 0 && <Thumbnails images={task.images} />}
diff --git a/webview-ui/src/components/chat/__tests__/TaskHeader.spec.tsx b/webview-ui/src/components/chat/__tests__/TaskHeader.spec.tsx
index 2a302e6b18..5a5f6055b4 100644
--- a/webview-ui/src/components/chat/__tests__/TaskHeader.spec.tsx
+++ b/webview-ui/src/components/chat/__tests__/TaskHeader.spec.tsx
@@ -329,4 +329,118 @@ describe("TaskHeader", () => {
 			expect(screen.getByText("25%")).toBeInTheDocument()
 		})
 	})
+
+	describe("Expanded task text markdown rendering", () => {
+		it("shows raw source while collapsed and formatted markdown when expanded", async () => {
+			const { container } = renderTaskHeader({
+				task: { type: "say", ts: Date.now(), text: "**bold** and `code`", images: [] },
+			})
+
+			// Collapsed state renders the raw task text (no markdown formatting yet).
+			expect(screen.getByText("**bold** and `code`")).toBeInTheDocument()
+			expect(container.querySelector("strong")).toBeNull()
+
+			// Expand the header by clicking the collapsed title.
+			fireEvent.click(screen.getByText("**bold** and `code`"))
+
+			// Expanded state applies markdown: **bold** becomes <strong>, `code` becomes <code>.
+			const bold = await screen.findByText("bold")
+			expect(bold.tagName).toBe("STRONG")
+			expect(container.querySelector("code")?.textContent).toBe("code")
+
+			// The raw markdown source must not be displayed verbatim in the expanded view.
+			expect(screen.queryByText("**bold** and `code`")).not.toBeInTheDocument()
+		})
+
+		it("uses the shared scrollable style for the expanded prompt box", () => {
+			const { container } = renderTaskHeader({
+				task: { type: "say", ts: Date.now(), text: "prompt", images: [] },
+			})
+
+			// Expand the header.
+			fireEvent.click(screen.getByText("prompt"))
+
+			// The prompt box must use the VS Code-style .scrollable scrollbar (hover-reveal),
+			// not a default always-visible Chromium scrollbar, so it matches the message list.
+			const scrollBox = container.querySelector(".scrollable")
+			expect(scrollBox).not.toBeNull()
+			expect(scrollBox?.className).toContain("max-h-80")
+		})
+
+		it("renders headings and lists in the expanded view", async () => {
+			const { container } = renderTaskHeader({
+				task: {
+					type: "say",
+					ts: Date.now(),
+					text: "# Heading\n- item one\n- item two",
+					images: [],
+				},
+			})
+
+			// Expand via the header container (the raw multi-line title is not a stable text target).
+			fireEvent.click(container.querySelector(".cursor-pointer")!)
+
+			const heading = await screen.findByRole("heading")
+			expect(heading.textContent).toBe("Heading")
+			expect(container.querySelector("ul li")).not.toBeNull()
+		})
+
+		it("does not collapse the panel when a rendered markdown link is clicked", async () => {
+			const { container } = renderTaskHeader({
+				task: {
+					type: "say",
+					ts: Date.now(),
+					text: "**bold** [example](https://example.com)",
+					images: [],
+				},
+			})
+
+			// Expand the header.
+			fireEvent.click(screen.getByText("**bold** [example](https://example.com)"))
+			const link = await screen.findByRole("link", { name: "example" })
+
+			// Clicking a rendered link must not toggle isTaskExpanded (the header click
+			// handler ignores anchor targets), so the expanded content stays visible.
+			fireEvent.click(link)
+			expect(container.querySelector("strong")).not.toBeNull()
+		})
+
+		it("keeps context mentions clickable in the expanded markdown view", async () => {
+			const { container } = renderTaskHeader({
+				task: {
+					type: "say",
+					ts: Date.now(),
+					text: "Inspect @/src/file.ts, @problems, and @terminal.",
+					images: [],
+				},
+			})
+
+			// Expand via the header container because the collapsed title contains split mention spans.
+			fireEvent.click(container.querySelector(".cursor-pointer")!)
+			await screen.findByText(/Inspect/, { exact: false })
+
+			const mentions = container.querySelectorAll("span.mention-context-highlight")
+			expect(mentions).toHaveLength(3)
+			expect(mentions[0].textContent).toBe("@/src/file.ts")
+			expect(mentions[1].textContent).toBe("@problems")
+			expect(mentions[2].textContent).toBe("@terminal")
+
+			fireEvent.click(mentions[0])
+			expect(mockPostMessage).toHaveBeenCalledWith({ type: "openMention", text: "/src/file.ts" })
+		})
+
+		it("renders an empty prompt without crashing", () => {
+			const { container } = renderTaskHeader({
+				// `text` is optional on ClineMessage; omit it to exercise the empty-prompt path.
+				task: { type: "say", ts: Date.now(), images: [] },
+			})
+
+			// No title text to click, so expand via the header container itself.
+			fireEvent.click(container.querySelector(".cursor-pointer")!)
+
+			// The empty prompt renders nothing but must not crash; the rest of the
+			// expanded header (cost row) is still present.
+			expect(screen.getByText("$0.05")).toBeInTheDocument()
+		})
+	})
 })
diff --git a/webview-ui/src/components/common/MarkdownBlock.tsx b/webview-ui/src/components/common/MarkdownBlock.tsx
index 02f696553f..200e197fbf 100644
--- a/webview-ui/src/components/common/MarkdownBlock.tsx
+++ b/webview-ui/src/components/common/MarkdownBlock.tsx
@@ -6,12 +6,66 @@ import rehypeKatex from "rehype-katex"
 import remarkMath from "remark-math"
 import remarkGfm from "remark-gfm"
 
+import { mentionRegexGlobal } from "@roo/context-mentions"
+
 import { vscode } from "@src/utils/vscode"
 import { type AlertType, remarkGithubAlerts } from "@src/utils/markdown"
 
 import CodeBlock from "./CodeBlock"
 import MermaidBlock from "./MermaidBlock"
 
+/**
+ * Rehype plugin that wraps context mentions (@/path, @problems, @terminal, etc.)
+ * in clickable spans matching the styling used by the collapsed Mention component.
+ */
+function rehypeMentions() {
+	return (tree: any) => {
+		visit(tree, "text", (node: any, index, parent) => {
+			if (parent?.tagName === "span" && parent.properties?.className?.includes("mention-context-highlight")) {
+				return
+			}
+
+			const originalValue = String(node.value)
+			const matches = Array.from(originalValue.matchAll(mentionRegexGlobal))
+
+			if (matches.length === 0) {
+				return
+			}
+
+			const children: any[] = []
+			let lastIndex = 0
+
+			for (const match of matches) {
+				const mentionText = match[0]
+				const mentionValue = match[1] ?? mentionText.slice(1) // capture group or full mention without @
+				const mentionStart = match.index!
+
+				if (mentionStart > lastIndex) {
+					children.push({ type: "text", value: originalValue.slice(lastIndex, mentionStart) })
+				}
+
+				children.push({
+					type: "element",
+					tagName: "span",
+					properties: {
+						className: ["mention-context-highlight", "text-[0.9em]", "cursor-pointer"],
+						onClick: () => vscode.postMessage({ type: "openMention", text: mentionValue }),
+					},
+					children: [{ type: "text", value: mentionText }],
+				})
+
+				lastIndex = mentionStart + mentionText.length
+			}
+
+			if (lastIndex < originalValue.length) {
+				children.push({ type: "text", value: originalValue.slice(lastIndex) })
+			}
+
+			parent.children.splice(index, 1, ...children)
+		})
+	}
+}
+
 // Codicon glyphs used as the leading icon for each GitHub-style alert type.
 const ALERT_ICONS: Record<AlertType, string> = {
 	note: "codicon-info",
@@ -415,7 +469,7 @@ const MarkdownBlock = memo(({ markdown }: MarkdownBlockProps) => {
 						}
 					},
 				]}
-				rehypePlugins={[rehypeKatex as any]}
+				rehypePlugins={[rehypeMentions, rehypeKatex as any]}
 				components={components}>
 				{markdown || ""}
 			</ReactMarkdown>
diff --git a/webview-ui/src/components/common/__tests__/MarkdownBlock.spec.tsx b/webview-ui/src/components/common/__tests__/MarkdownBlock.spec.tsx
index 2c56fc418a..bdd476ae08 100644
--- a/webview-ui/src/components/common/__tests__/MarkdownBlock.spec.tsx
+++ b/webview-ui/src/components/common/__tests__/MarkdownBlock.spec.tsx
@@ -1,13 +1,21 @@
-import { render, screen } from "@/utils/test-utils"
+import { render, screen, fireEvent } from "@/utils/test-utils"
 
 import MarkdownBlock from "../MarkdownBlock"
 
+const { mockPostMessage } = vi.hoisted(() => ({
+	mockPostMessage: vi.fn(),
+}))
+
 vi.mock("@src/utils/vscode", () => ({
 	vscode: {
-		postMessage: vi.fn(),
+		postMessage: mockPostMessage,
 	},
 }))
 
+beforeEach(() => {
+	mockPostMessage.mockClear()
+})
+
 vi.mock("@src/context/ExtensionStateContext", () => ({
 	useExtensionState: () => ({
 		theme: "dark",
@@ -217,4 +225,98 @@ describe("MarkdownBlock", () => {
 		expect(screen.getByText("Third level ordered")).toBeInTheDocument()
 		expect(screen.getByText("Back to first level")).toBeInTheDocument()
 	})
+
+	describe("Context mentions (#559)", () => {
+		it("renders @/path/file.ts as a clickable mention span", async () => {
+			const markdown = "Check out @/src/components/chat/TaskHeader.tsx for details."
+			const { container } = render(<MarkdownBlock markdown={markdown} />)
+
+			await screen.findByText(/Check out/, { exact: false })
+
+			// The mention should be wrapped in a span with the mention-context-highlight class.
+			const mentions = container.querySelectorAll("span.mention-context-highlight")
+			expect(mentions.length).toBe(1)
+			expect(mentions[0].textContent).toBe("@/src/components/chat/TaskHeader.tsx")
+
+			// The trailing period must remain outside the mention span.
+			expect(container.querySelector("p")?.textContent).toBe(
+				"Check out @/src/components/chat/TaskHeader.tsx for details.",
+			)
+		})
+
+		it("renders @problems as a clickable mention span", async () => {
+			const markdown = "Review the issues listed in @problems before proceeding."
+			const { container } = render(<MarkdownBlock markdown={markdown} />)
+
+			await screen.findByText(/Review/, { exact: false })
+
+			const mentions = container.querySelectorAll("span.mention-context-highlight")
+			expect(mentions.length).toBe(1)
+			expect(mentions[0].textContent).toBe("@problems")
+		})
+
+		it("renders @terminal as a clickable mention span", async () => {
+			const markdown = "See the output captured in @terminal."
+			const { container } = render(<MarkdownBlock markdown={markdown} />)
+
+			await screen.findByText(/See/, { exact: false })
+
+			const mentions = container.querySelectorAll("span.mention-context-highlight")
+			expect(mentions.length).toBe(1)
+			expect(mentions[0].textContent).toBe("@terminal")
+		})
+
+		it("renders multiple mentions in the same paragraph", async () => {
+			const markdown = "Check @/src/file.ts and @problems, then review @terminal."
+			const { container } = render(<MarkdownBlock markdown={markdown} />)
+
+			await screen.findByText(/Check/, { exact: false })
+
+			const mentions = container.querySelectorAll("span.mention-context-highlight")
+			expect(mentions.length).toBe(3)
+			expect(mentions[0].textContent).toBe("@/src/file.ts")
+			expect(mentions[1].textContent).toBe("@problems")
+			expect(mentions[2].textContent).toBe("@terminal")
+		})
+
+		it("posts openMention message when a mention span is clicked", async () => {
+			const markdown = "See @/src/components/chat/TaskHeader.tsx."
+			const { container } = render(<MarkdownBlock markdown={markdown} />)
+
+			await screen.findByText(/See/, { exact: false })
+
+			const mentionSpan = container.querySelector("span.mention-context-highlight")!
+			fireEvent.click(mentionSpan)
+
+			expect(mockPostMessage).toHaveBeenCalledWith({
+				type: "openMention",
+				text: "/src/components/chat/TaskHeader.tsx",
+			})
+		})
+
+		it("does not match @ in the middle of a word or log entry", async () => {
+			const markdown = "Error: Failed@localhost/status code 404."
+			const { container } = render(<MarkdownBlock markdown={markdown} />)
+
+			await screen.findByText(/Error/, { exact: false })
+
+			const mentions = container.querySelectorAll("span.mention-context-highlight")
+			expect(mentions.length).toBe(0)
+		})
+
+		it("preserves regular text around mentions", async () => {
+			const markdown = "Before @problems middle after"
+			const { container } = render(<MarkdownBlock markdown={markdown} />)
+
+			await screen.findByText(/Before/, { exact: false })
+
+			const paragraph = container.querySelector("p")
+			expect(paragraph?.textContent).toBe("Before @problems middle after")
+
+			// The mention span should only contain the mention itself.
+			const mentions = container.querySelectorAll("span.mention-context-highlight")
+			expect(mentions.length).toBe(1)
+			expect(mentions[0].textContent).toBe("@problems")
+		})
+	})
 })