diff --git a/site/src/components/Markdown/Markdown.stories.tsx b/site/src/components/Markdown/Markdown.stories.tsx
index d4adce530e..37a0670c73 100644
--- a/site/src/components/Markdown/Markdown.stories.tsx
+++ b/site/src/components/Markdown/Markdown.stories.tsx
@@ -74,3 +74,24 @@ export const WithTable: Story = {
   | cell 1 | cell 2 | 3 | 4 | `,
 	},
 };
+
+export const GFMAlerts: Story = {
+	args: {
+		children: `
+> [!NOTE]
+> Useful information that users should know, even when skimming content.
+
+> [!TIP]
+> Helpful advice for doing things better or more easily.
+
+> [!IMPORTANT]
+> Key information users need to know to achieve their goal.
+
+> [!WARNING]
+> Urgent info that needs immediate user attention to avoid problems.
+
+> [!CAUTION]
+> Advises about risks or negative outcomes of certain actions.
+		`,
+	},
+};
diff --git a/site/src/components/Markdown/Markdown.tsx b/site/src/components/Markdown/Markdown.tsx
index a9bac7c6ad..b68919dce5 100644
--- a/site/src/components/Markdown/Markdown.tsx
+++ b/site/src/components/Markdown/Markdown.tsx
@@ -8,12 +8,20 @@ import {
 	TableRow,
 } from "components/Table/Table";
 import isEqual from "lodash/isEqual";
-import { type FC, memo } from "react";
+import {
+	type FC,
+	type HTMLProps,
+	type ReactElement,
+	type ReactNode,
+	isValidElement,
+	memo,
+} from "react";
 import ReactMarkdown, { type Options } from "react-markdown";
 import { Prism as SyntaxHighlighter } from "react-syntax-highlighter";
 import { dracula } from "react-syntax-highlighter/dist/cjs/styles/prism";
 import gfm from "remark-gfm";
 import colors from "theme/tailwindColors";
+import { cn } from "utils/cn";
 
 interface MarkdownProps {
 	/**
@@ -114,6 +122,30 @@ export const Markdown: FC<MarkdownProps> = (props) => {
 					return <TableCell>{children}</TableCell>;
 				},
 
+				/**
+				 * 2025-02-10 - The RemarkGFM plugin that we use currently doesn't have
+				 * support for special alert messages like this:
+				 * ```
+				 * > [!IMPORTANT]
+				 * > This module will only work with Git versions >=2.34, and...
+				 * ```
+				 * Have to intercept all blockquotes and see if their content is
+				 * formatted like an alert.
+				 */
+				blockquote: (parseProps) => {
+					const { node: _node, children, ...renderProps } = parseProps;
+					const alertContent = parseChildrenAsAlertContent(children);
+					if (alertContent === null) {
+						return <blockquote {...renderProps}>{children}</blockquote>;
+					}
+
+					return (
+						<MarkdownGfmAlert alertType={alertContent.type} {...renderProps}>
+							{alertContent.children}
+						</MarkdownGfmAlert>
+					);
+				},
+
 				...components,
 			}}
 		>
@@ -197,6 +229,149 @@ export const InlineMarkdown: FC<InlineMarkdownProps> = (props) => {
 export const MemoizedMarkdown = memo(Markdown, isEqual);
 export const MemoizedInlineMarkdown = memo(InlineMarkdown, isEqual);
 
+const githubFlavoredMarkdownAlertTypes = [
+	"tip",
+	"note",
+	"important",
+	"warning",
+	"caution",
+];
+
+type AlertContent = Readonly<{
+	type: string;
+	children: readonly ReactNode[];
+}>;
+
+function parseChildrenAsAlertContent(
+	jsxChildren: ReactNode,
+): AlertContent | null {
+	// Have no idea why the plugin parses the data by mixing node types
+	// like this. Have to do a good bit of nested filtering.
+	if (!Array.isArray(jsxChildren)) {
+		return null;
+	}
+
+	const mainParentNode = jsxChildren.find((node): node is ReactElement =>
+		isValidElement(node),
+	);
+	let parentChildren = mainParentNode?.props.children;
+	if (typeof parentChildren === "string") {
+		// Children will only be an array if the parsed text contains other
+		// content that can be turned into HTML. If there aren't any, you
+		// just get one big string
+		parentChildren = parentChildren.split("\n");
+	}
+	if (!Array.isArray(parentChildren)) {
+		return null;
+	}
+
+	const outputContent = parentChildren
+		.filter((el) => {
+			if (isValidElement(el)) {
+				return true;
+			}
+			return typeof el === "string" && el !== "\n";
+		})
+		.map((el) => {
+			if (!isValidElement(el)) {
+				return el;
+			}
+			if (el.type !== "a") {
+				return el;
+			}
+
+			const recastProps = el.props as Record<string, unknown> & {
+				children?: ReactNode;
+			};
+			if (recastProps.target === "_blank") {
+				return el;
+			}
+
+			return {
+				...el,
+				props: {
+					...recastProps,
+					target: "_blank",
+					children: (
+						<>
+							{recastProps.children}
+							<span className="sr-only"> (link opens in new tab)</span>
+						</>
+					),
+				},
+			};
+		});
+	const [firstEl, ...remainingChildren] = outputContent;
+	if (typeof firstEl !== "string") {
+		return null;
+	}
+
+	const alertType = firstEl
+		.trim()
+		.toLowerCase()
+		.replace("!", "")
+		.replace("[", "")
+		.replace("]", "");
+	if (!githubFlavoredMarkdownAlertTypes.includes(alertType)) {
+		return null;
+	}
+
+	const hasLeadingLinebreak =
+		isValidElement(remainingChildren[0]) && remainingChildren[0].type === "br";
+	if (hasLeadingLinebreak) {
+		remainingChildren.shift();
+	}
+
+	return {
+		type: alertType,
+		children: remainingChildren,
+	};
+}
+
+type MarkdownGfmAlertProps = Readonly<
+	HTMLProps<HTMLElement> & {
+		alertType: string;
+	}
+>;
+
+const MarkdownGfmAlert: FC<MarkdownGfmAlertProps> = ({
+	alertType,
+	children,
+	...delegatedProps
+}) => {
+	return (
+		<div className="pb-6">
+			<aside
+				{...delegatedProps}
+				className={cn(
+					"border-0 border-l-4 border-solid border-border p-4 text-white",
+					"[&_p]:m-0 [&_p]:mb-2",
+
+					alertType === "important" &&
+						"border-highlight-purple [&_p:first-child]:text-highlight-purple",
+
+					alertType === "warning" &&
+						"border-border-warning [&_p:first-child]:text-border-warning",
+
+					alertType === "note" &&
+						"border-highlight-sky [&_p:first-child]:text-highlight-sky",
+
+					alertType === "tip" &&
+						"border-highlight-green [&_p:first-child]:text-highlight-green",
+
+					alertType === "caution" &&
+						"border-highlight-red [&_p:first-child]:text-highlight-red",
+				)}
+			>
+				<p className="font-bold">
+					{alertType[0]?.toUpperCase() + alertType.slice(1).toLowerCase()}
+				</p>
+				{children}
+			</aside>
+		</div>
+	);
+};
+
 const markdownStyles: Interpolation<Theme> = (theme: Theme) => ({
 	fontSize: 16,
 	lineHeight: "24px",
diff --git a/site/src/index.css b/site/src/index.css
index e2b71d7be6..f3bf0918dd 100644
--- a/site/src/index.css
+++ b/site/src/index.css
@@ -29,6 +29,7 @@
 		--surface-orange: 34 100% 92%;
 		--surface-sky: 201 94% 86%;
 		--surface-red: 0 93% 94%;
+		--surface-purple: 251 91% 95%;
 		--border-default: 240 6% 90%;
 		--border-success: 142 76% 36%;
 		--border-warning: 30.66, 97.16%, 72.35%;
@@ -41,6 +42,7 @@
 		--highlight-green: 143 64% 24%;
 		--highlight-grey: 240 5% 65%;
 		--highlight-sky: 201 90% 27%;
+		--highlight-red: 0 74% 42%;
 		--border: 240 5.9% 90%;
 		--input: 240 5.9% 90%;
 		--ring: 240 10% 3.9%;
@@ -69,6 +71,7 @@
 		--surface-orange: 13 81% 15%;
 		--surface-sky: 204 80% 16%;
 		--surface-red: 0 75% 15%;
+		--surface-purple: 261 73% 23%;
 		--border-default: 240 4% 16%;
 		--border-success: 142 76% 36%;
 		--border-warning: 30.66, 97.16%, 72.35%;
@@ -80,6 +83,7 @@
 		--highlight-green: 141 79% 85%;
 		--highlight-grey: 240 4% 46%;
 		--highlight-sky: 198 93% 60%;
+		--highlight-red: 0 91% 71%;
 		--border: 240 3.7% 15.9%;
 		--input: 240 3.7% 15.9%;
 		--ring: 240 4.9% 83.9%;
diff --git a/site/tailwind.config.js b/site/tailwind.config.js
index d2935698e5..e4b40aa177 100644
--- a/site/tailwind.config.js
+++ b/site/tailwind.config.js
@@ -53,6 +53,7 @@ module.exports = {
 					orange: "hsl(var(--surface-orange))",
 					sky: "hsl(var(--surface-sky))",
 					red: "hsl(var(--surface-red))",
+					purple: "hsl(var(--surface-purple))",
 				},
 				border: {
 					DEFAULT: "hsl(var(--border-default))",
@@ -69,6 +70,7 @@ module.exports = {
 					green: "hsl(var(--highlight-green))",
 					grey: "hsl(var(--highlight-grey))",
 					sky: "hsl(var(--highlight-sky))",
+					red: "hsl(var(--highlight-red))",
 				},
 			},
 			keyframes: {