diff --git a/site/e2e/helpers.ts b/site/e2e/helpers.ts
index 71b1c039c5dfb..85a9283abae04 100644
--- a/site/e2e/helpers.ts
+++ b/site/e2e/helpers.ts
@@ -1042,7 +1042,9 @@ export async function openTerminalWindow(
 ): Promise<Page> {
 	// Wait for the web terminal to open in a new tab
 	const pagePromise = context.waitForEvent("page");
-	await page.getByTestId("terminal").click({ timeout: 60_000 });
+	await page
+		.getByRole("link", { name: /terminal/i })
+		.click({ timeout: 60_000 });
 	const terminal = await pagePromise;
 	await terminal.waitForLoadState("domcontentloaded");
 
diff --git a/site/src/components/Button/Button.tsx b/site/src/components/Button/Button.tsx
index f3940fe45cabc..908dacb8c5c3d 100644
--- a/site/src/components/Button/Button.tsx
+++ b/site/src/components/Button/Button.tsx
@@ -13,7 +13,9 @@ const buttonVariants = cva(
 	text-sm font-semibold font-medium cursor-pointer no-underline
 	focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-content-link
 	disabled:pointer-events-none disabled:text-content-disabled
-	[&_svg]:pointer-events-none [&_svg]:shrink-0 [&_svg]:p-0.5`,
+	[&:is(a):not([href])]:pointer-events-none [&:is(a):not([href])]:text-content-disabled
+	[&_svg]:pointer-events-none [&_svg]:shrink-0 [&_svg]:p-0.5
+	[&>img]:pointer-events-none [&>img]:shrink-0 [&>img]:p-0.5`,
 	{
 		variants: {
 			variant: {
@@ -28,11 +30,11 @@ const buttonVariants = cva(
 			},
 
 			size: {
-				lg: "min-w-20 h-10 px-3 py-2 [&_svg]:size-icon-lg",
-				sm: "min-w-20 h-8 px-2 py-1.5 text-xs [&_svg]:size-icon-sm",
+				lg: "min-w-20 h-10 px-3 py-2 [&_svg]:size-icon-lg [&>img]:size-icon-lg",
+				sm: "min-w-20 h-8 px-2 py-1.5 text-xs [&_svg]:size-icon-sm [&>img]:size-icon-sm",
 				xs: "min-w-8 py-1 px-2 text-2xs rounded-md",
-				icon: "size-8 px-1.5 [&_svg]:size-icon-sm",
-				"icon-lg": "size-10 px-2 [&_svg]:size-icon-lg",
+				icon: "size-8 px-1.5 [&_svg]:size-icon-sm [&>img]:size-icon-sm",
+				"icon-lg": "size-10 px-2 [&_svg]:size-icon-lg [&>img]:size-icon-lg",
 			},
 		},
 		defaultVariants: {
diff --git a/site/src/components/ExternalImage/ExternalImage.tsx b/site/src/components/ExternalImage/ExternalImage.tsx
index b15af07944ca8..d85b227b999b4 100644
--- a/site/src/components/ExternalImage/ExternalImage.tsx
+++ b/site/src/components/ExternalImage/ExternalImage.tsx
@@ -5,15 +5,15 @@ import { getExternalImageStylesFromUrl } from "theme/externalImages";
 export const ExternalImage = forwardRef<
 	HTMLImageElement,
 	ImgHTMLAttributes<HTMLImageElement>
->((attrs, ref) => {
+>((props, ref) => {
 	const theme = useTheme();
 
 	return (
-		// biome-ignore lint/a11y/useAltText: no reasonable alt to provide
+		// biome-ignore lint/a11y/useAltText: alt should be passed in as a prop
 		<img
 			ref={ref}
-			css={getExternalImageStylesFromUrl(theme.externalImages, attrs.src)}
-			{...attrs}
+			css={getExternalImageStylesFromUrl(theme.externalImages, props.src)}
+			{...props}
 		/>
 	);
 });
diff --git a/site/src/modules/dashboard/Navbar/ProxyMenu.tsx b/site/src/modules/dashboard/Navbar/ProxyMenu.tsx
index 86d9b9b53ee84..97e360984357f 100644
--- a/site/src/modules/dashboard/Navbar/ProxyMenu.tsx
+++ b/site/src/modules/dashboard/Navbar/ProxyMenu.tsx
@@ -81,32 +81,25 @@ export const ProxyMenu: FC<ProxyMenuProps> = ({ proxyContextValue }) => {
 				</span>
 
 				{selectedProxy ? (
-					<div css={{ display: "flex", gap: 8, alignItems: "center" }}>
-						<div css={{ width: 16, height: 16, lineHeight: 0 }}>
-							<img
-								// Empty alt text used because we don't want to double up on
-								// screen reader announcements from visually-hidden span
-								alt=""
-								src={selectedProxy.icon_url}
-								css={{
-									objectFit: "contain",
-									width: "100%",
-									height: "100%",
-								}}
-							/>
-						</div>
+					<>
+						<img
+							// Empty alt text used because we don't want to double up on
+							// screen reader announcements from visually-hidden span
+							alt=""
+							src={selectedProxy.icon_url}
+						/>
 
 						<Latency
 							latency={latencies?.[selectedProxy.id]?.latencyMS}
 							isLoading={proxyLatencyLoading(selectedProxy)}
 							size={24}
 						/>
-					</div>
+					</>
 				) : (
 					"Select Proxy"
 				)}
 
-				<ChevronDownIcon className="text-content-primary !size-icon-xs" />
+				<ChevronDownIcon className="text-content-primary !size-icon-sm" />
 			</Button>
 
 			<Menu
diff --git a/site/src/modules/management/OrganizationSidebarView.tsx b/site/src/modules/management/OrganizationSidebarView.tsx
index 5de8ef0d2ee4d..a03dc62b65c0e 100644
--- a/site/src/modules/management/OrganizationSidebarView.tsx
+++ b/site/src/modules/management/OrganizationSidebarView.tsx
@@ -62,25 +62,23 @@ export const OrganizationSidebarView: FC<
 					<Button
 						variant="outline"
 						aria-expanded={isPopoverOpen}
-						className="w-60 justify-between p-2 h-11"
+						className="w-60 gap-2 justify-start"
 					>
-						<div className="flex flex-row gap-2 items-center p-2 truncate">
-							{activeOrganization ? (
-								<>
-									<Avatar
-										size="sm"
-										src={activeOrganization.icon}
-										fallback={activeOrganization.display_name}
-									/>
-									<span className="truncate">
-										{activeOrganization.display_name || activeOrganization.name}
-									</span>
-								</>
-							) : (
-								<span className="truncate">No organization selected</span>
-							)}
-						</div>
-						<ChevronDown />
+						{activeOrganization ? (
+							<>
+								<Avatar
+									size="sm"
+									src={activeOrganization.icon}
+									fallback={activeOrganization.display_name}
+								/>
+								<span className="truncate">
+									{activeOrganization.display_name || activeOrganization.name}
+								</span>
+							</>
+						) : (
+							<span className="truncate">No organization selected</span>
+						)}
+						<ChevronDown className="ml-auto !size-icon-sm" />
 					</Button>
 				</PopoverTrigger>
 				<PopoverContent align="start" className="w-60">
diff --git a/site/src/modules/resources/AgentButton.tsx b/site/src/modules/resources/AgentButton.tsx
index 2f772e4f8e0ca..e5b4a54834531 100644
--- a/site/src/modules/resources/AgentButton.tsx
+++ b/site/src/modules/resources/AgentButton.tsx
@@ -1,31 +1,8 @@
-import Button, { type ButtonProps } from "@mui/material/Button";
+import { Button, type ButtonProps } from "components/Button/Button";
 import { forwardRef } from "react";
 
 export const AgentButton = forwardRef<HTMLButtonElement, ButtonProps>(
 	(props, ref) => {
-		const { children, ...buttonProps } = props;
-
-		return (
-			<Button
-				{...buttonProps}
-				color="neutral"
-				size="xlarge"
-				variant="contained"
-				ref={ref}
-				css={(theme) => ({
-					padding: "12px 20px",
-					color: theme.palette.text.primary,
-					// Making them smaller since those icons don't have a padding around them
-					"& .MuiButton-startIcon, & .MuiButton-endIcon": {
-						width: 16,
-						height: 16,
-
-						"& svg, & img": { width: "100%", height: "100%" },
-					},
-				})}
-			>
-				{children}
-			</Button>
-		);
+		return <Button variant="outline" ref={ref} {...props} />;
 	},
 );
diff --git a/site/src/modules/resources/AgentDevcontainerCard.tsx b/site/src/modules/resources/AgentDevcontainerCard.tsx
index 91a90a75db85f..d9a591625b2f8 100644
--- a/site/src/modules/resources/AgentDevcontainerCard.tsx
+++ b/site/src/modules/resources/AgentDevcontainerCard.tsx
@@ -1,10 +1,14 @@
-import Link from "@mui/material/Link";
-import Tooltip from "@mui/material/Tooltip";
 import type {
 	Workspace,
 	WorkspaceAgent,
 	WorkspaceAgentContainer,
 } from "api/typesGenerated";
+import {
+	Tooltip,
+	TooltipContent,
+	TooltipProvider,
+	TooltipTrigger,
+} from "components/Tooltip/Tooltip";
 import { ExternalLinkIcon } from "lucide-react";
 import type { FC } from "react";
 import { portForwardURL } from "utils/portForward";
@@ -74,7 +78,7 @@ export const AgentDevcontainerCard: FC<AgentDevcontainerCardProps> = ({
 						const linkDest = hasHostBind
 							? portForwardURL(
 									wildcardHostname,
-									port.host_port!,
+									port.host_port,
 									agent.name,
 									workspace.name,
 									workspace.owner_name,
@@ -82,21 +86,19 @@ export const AgentDevcontainerCard: FC<AgentDevcontainerCardProps> = ({
 								)
 							: "";
 						return (
-							<Tooltip key={portLabel} title={helperText}>
-								<span>
-									<Link
-										key={portLabel}
-										color="inherit"
-										component={AgentButton}
-										underline="none"
-										startIcon={<ExternalLinkIcon className="size-icon-sm" />}
-										disabled={!hasHostBind}
-										href={linkDest}
-									>
-										{portLabel}
-									</Link>
-								</span>
-							</Tooltip>
+							<TooltipProvider key={portLabel}>
+								<Tooltip>
+									<TooltipTrigger>
+										<AgentButton disabled={!hasHostBind} asChild>
+											<a href={linkDest}>
+												<ExternalLinkIcon />
+												{portLabel}
+											</a>
+										</AgentButton>
+									</TooltipTrigger>
+									<TooltipContent>{helperText}</TooltipContent>
+								</Tooltip>
+							</TooltipProvider>
 						);
 					})}
 			</div>
diff --git a/site/src/modules/resources/AppLink/AppLink.tsx b/site/src/modules/resources/AppLink/AppLink.tsx
index 5bf2114acf879..8eeef61ee920e 100644
--- a/site/src/modules/resources/AppLink/AppLink.tsx
+++ b/site/src/modules/resources/AppLink/AppLink.tsx
@@ -1,13 +1,17 @@
 import { useTheme } from "@emotion/react";
 import ErrorOutlineIcon from "@mui/icons-material/ErrorOutline";
-import CircularProgress from "@mui/material/CircularProgress";
-import Link from "@mui/material/Link";
-import Tooltip from "@mui/material/Tooltip";
 import { API } from "api/api";
 import type * as TypesGen from "api/typesGenerated";
 import { displayError } from "components/GlobalSnackbar/utils";
+import { Spinner } from "components/Spinner/Spinner";
+import {
+	Tooltip,
+	TooltipContent,
+	TooltipProvider,
+	TooltipTrigger,
+} from "components/Tooltip/Tooltip";
 import { useProxy } from "contexts/ProxyContext";
-import { type FC, type MouseEvent, useState } from "react";
+import { type FC, useState } from "react";
 import { createAppLinkHref } from "utils/apps";
 import { generateRandomString } from "utils/random";
 import { AgentButton } from "../AgentButton";
@@ -75,21 +79,7 @@ export const AppLink: FC<AppLinkProps> = ({ app, workspace, agent }) => {
 
 	let primaryTooltip = "";
 	if (app.health === "initializing") {
-		icon = (
-			// This is a hack to make the spinner appear in the center of the start
-			// icon space
-			<span
-				css={{
-					display: "flex",
-					width: "100%",
-					height: "100%",
-					alignItems: "center",
-					justifyContent: "center",
-				}}
-			>
-				<CircularProgress size={14} />
-			</span>
-		);
+		icon = <Spinner loading />;
 		primaryTooltip = "Initializing...";
 	}
 	if (app.health === "unhealthy") {
@@ -112,22 +102,13 @@ export const AppLink: FC<AppLinkProps> = ({ app, workspace, agent }) => {
 		canClick = false;
 	}
 
-	const isPrivateApp = app.sharing_level === "owner";
-
-	return (
-		<Tooltip title={primaryTooltip}>
-			<Link
-				color="inherit"
-				component={AgentButton}
-				startIcon={icon}
-				endIcon={isPrivateApp ? undefined : <ShareIcon app={app} />}
-				disabled={!canClick}
-				href={href}
-				css={{
-					pointerEvents: canClick ? undefined : "none",
-					textDecoration: "none !important",
-				}}
-				onClick={async (event: MouseEvent<HTMLElement>) => {
+	const canShare = app.sharing_level !== "owner";
+
+	const button = (
+		<AgentButton asChild>
+			<a
+				href={canClick ? href : undefined}
+				onClick={async (event) => {
 					if (!canClick) {
 						return;
 					}
@@ -187,8 +168,23 @@ export const AppLink: FC<AppLinkProps> = ({ app, workspace, agent }) => {
 					}
 				}}
 			>
+				{icon}
 				{appDisplayName}
-			</Link>
-		</Tooltip>
+				{canShare && <ShareIcon app={app} />}
+			</a>
+		</AgentButton>
 	);
+
+	if (primaryTooltip) {
+		return (
+			<TooltipProvider>
+				<Tooltip>
+					<TooltipTrigger asChild>{button}</TooltipTrigger>
+					<TooltipContent>{primaryTooltip}</TooltipContent>
+				</Tooltip>
+			</TooltipProvider>
+		);
+	}
+
+	return button;
 };
diff --git a/site/src/modules/resources/TerminalLink/TerminalLink.tsx b/site/src/modules/resources/TerminalLink/TerminalLink.tsx
index 6a4e6d41f3ffc..23204bd819dfe 100644
--- a/site/src/modules/resources/TerminalLink/TerminalLink.tsx
+++ b/site/src/modules/resources/TerminalLink/TerminalLink.tsx
@@ -1,4 +1,3 @@
-import Link from "@mui/material/Link";
 import { TerminalIcon } from "components/Icons/TerminalIcon";
 import type { FC, MouseEvent } from "react";
 import { generateRandomString } from "utils/random";
@@ -39,23 +38,21 @@ export const TerminalLink: FC<TerminalLinkProps> = ({
 	}/terminal?${params.toString()}`;
 
 	return (
-		<Link
-			underline="none"
-			color="inherit"
-			component={AgentButton}
-			startIcon={<TerminalIcon />}
-			href={href}
-			onClick={(event: MouseEvent<HTMLElement>) => {
-				event.preventDefault();
-				window.open(
-					href,
-					Language.terminalTitle(generateRandomString(12)),
-					"width=900,height=600",
-				);
-			}}
-			data-testid="terminal"
-		>
-			{DisplayAppNameMap.web_terminal}
-		</Link>
+		<AgentButton asChild>
+			<a
+				href={href}
+				onClick={(event: MouseEvent<HTMLElement>) => {
+					event.preventDefault();
+					window.open(
+						href,
+						Language.terminalTitle(generateRandomString(12)),
+						"width=900,height=600",
+					);
+				}}
+			>
+				<TerminalIcon />
+				{DisplayAppNameMap.web_terminal}
+			</a>
+		</AgentButton>
 	);
 };
diff --git a/site/src/modules/resources/VSCodeDesktopButton/VSCodeDesktopButton.tsx b/site/src/modules/resources/VSCodeDesktopButton/VSCodeDesktopButton.tsx
index 10193660155eb..8397305ef153f 100644
--- a/site/src/modules/resources/VSCodeDesktopButton/VSCodeDesktopButton.tsx
+++ b/site/src/modules/resources/VSCodeDesktopButton/VSCodeDesktopButton.tsx
@@ -1,11 +1,10 @@
-import KeyboardArrowDownIcon from "@mui/icons-material/KeyboardArrowDown";
-import ButtonGroup from "@mui/material/ButtonGroup";
 import Menu from "@mui/material/Menu";
 import MenuItem from "@mui/material/MenuItem";
 import { API } from "api/api";
 import type { DisplayApp } from "api/typesGenerated";
 import { VSCodeIcon } from "components/Icons/VSCodeIcon";
 import { VSCodeInsidersIcon } from "components/Icons/VSCodeInsidersIcon";
+import { ChevronDownIcon } from "lucide-react";
 import { type FC, useRef, useState } from "react";
 import { AgentButton } from "../AgentButton";
 import { DisplayAppNameMap } from "../AppLink/AppLink";
@@ -43,8 +42,8 @@ export const VSCodeDesktopButton: FC<VSCodeDesktopButtonProps> = (props) => {
 	const includesVSCodeInsiders = props.displayApps.includes("vscode_insiders");
 
 	return includesVSCodeDesktop && includesVSCodeInsiders ? (
-		<div>
-			<ButtonGroup ref={menuAnchorRef} variant="outlined">
+		<>
+			<div ref={menuAnchorRef} className="flex items-center gap-1">
 				{variant === "vscode" ? (
 					<VSCodeButton {...props} />
 				) : (
@@ -58,15 +57,14 @@ export const VSCodeDesktopButton: FC<VSCodeDesktopButtonProps> = (props) => {
 					aria-expanded={isVariantMenuOpen ? "true" : undefined}
 					aria-label="select VSCode variant"
 					aria-haspopup="menu"
-					disableRipple
 					onClick={() => {
 						setIsVariantMenuOpen(true);
 					}}
-					css={{ paddingLeft: 0, paddingRight: 0 }}
+					size="icon-lg"
 				>
-					<KeyboardArrowDownIcon css={{ fontSize: 16 }} />
+					<ChevronDownIcon />
 				</AgentButton>
-			</ButtonGroup>
+			</div>
 
 			<Menu
 				open={isVariantMenuOpen}
@@ -97,7 +95,7 @@ export const VSCodeDesktopButton: FC<VSCodeDesktopButtonProps> = (props) => {
 					{DisplayAppNameMap.vscode_insiders}
 				</MenuItem>
 			</Menu>
-		</div>
+		</>
 	) : includesVSCodeDesktop ? (
 		<VSCodeButton {...props} />
 	) : (
@@ -115,7 +113,6 @@ const VSCodeButton: FC<VSCodeDesktopButtonProps> = ({
 
 	return (
 		<AgentButton
-			startIcon={<VSCodeIcon />}
 			disabled={loading}
 			onClick={() => {
 				setLoading(true);
@@ -145,6 +142,7 @@ const VSCodeButton: FC<VSCodeDesktopButtonProps> = ({
 					});
 			}}
 		>
+			<VSCodeIcon />
 			{DisplayAppNameMap.vscode}
 		</AgentButton>
 	);
@@ -160,7 +158,6 @@ const VSCodeInsidersButton: FC<VSCodeDesktopButtonProps> = ({
 
 	return (
 		<AgentButton
-			startIcon={<VSCodeInsidersIcon />}
 			disabled={loading}
 			onClick={() => {
 				setLoading(true);
@@ -189,6 +186,7 @@ const VSCodeInsidersButton: FC<VSCodeDesktopButtonProps> = ({
 					});
 			}}
 		>
+			<VSCodeInsidersIcon />
 			{DisplayAppNameMap.vscode_insiders}
 		</AgentButton>
 	);
diff --git a/site/src/modules/resources/VSCodeDevContainerButton/VSCodeDevContainerButton.tsx b/site/src/modules/resources/VSCodeDevContainerButton/VSCodeDevContainerButton.tsx
index 3b32c672e8e8f..cbd5aba4efa90 100644
--- a/site/src/modules/resources/VSCodeDevContainerButton/VSCodeDevContainerButton.tsx
+++ b/site/src/modules/resources/VSCodeDevContainerButton/VSCodeDevContainerButton.tsx
@@ -1,11 +1,10 @@
-import KeyboardArrowDownIcon from "@mui/icons-material/KeyboardArrowDown";
-import ButtonGroup from "@mui/material/ButtonGroup";
 import Menu from "@mui/material/Menu";
 import MenuItem from "@mui/material/MenuItem";
 import { API } from "api/api";
 import type { DisplayApp } from "api/typesGenerated";
 import { VSCodeIcon } from "components/Icons/VSCodeIcon";
 import { VSCodeInsidersIcon } from "components/Icons/VSCodeInsidersIcon";
+import { ChevronDownIcon } from "lucide-react";
 import { type FC, useRef, useState } from "react";
 import { AgentButton } from "../AgentButton";
 import { DisplayAppNameMap } from "../AppLink/AppLink";
@@ -46,8 +45,8 @@ export const VSCodeDevContainerButton: FC<VSCodeDevContainerButtonProps> = (
 	const includesVSCodeInsiders = props.displayApps.includes("vscode_insiders");
 
 	return includesVSCodeDesktop && includesVSCodeInsiders ? (
-		<div>
-			<ButtonGroup ref={menuAnchorRef} variant="outlined">
+		<>
+			<div ref={menuAnchorRef} className="flex items-center gap-1">
 				{variant === "vscode" ? (
 					<VSCodeButton {...props} />
 				) : (
@@ -61,15 +60,14 @@ export const VSCodeDevContainerButton: FC<VSCodeDevContainerButtonProps> = (
 					aria-expanded={isVariantMenuOpen ? "true" : undefined}
 					aria-label="select VSCode variant"
 					aria-haspopup="menu"
-					disableRipple
 					onClick={() => {
 						setIsVariantMenuOpen(true);
 					}}
-					css={{ paddingLeft: 0, paddingRight: 0 }}
+					size="icon-lg"
 				>
-					<KeyboardArrowDownIcon css={{ fontSize: 16 }} />
+					<ChevronDownIcon />
 				</AgentButton>
-			</ButtonGroup>
+			</div>
 
 			<Menu
 				open={isVariantMenuOpen}
@@ -100,7 +98,7 @@ export const VSCodeDevContainerButton: FC<VSCodeDevContainerButtonProps> = (
 					{DisplayAppNameMap.vscode_insiders}
 				</MenuItem>
 			</Menu>
-		</div>
+		</>
 	) : includesVSCodeDesktop ? (
 		<VSCodeButton {...props} />
 	) : (
@@ -119,7 +117,6 @@ const VSCodeButton: FC<VSCodeDevContainerButtonProps> = ({
 
 	return (
 		<AgentButton
-			startIcon={<VSCodeIcon />}
 			disabled={loading}
 			onClick={() => {
 				setLoading(true);
@@ -147,6 +144,7 @@ const VSCodeButton: FC<VSCodeDevContainerButtonProps> = ({
 					});
 			}}
 		>
+			<VSCodeIcon />
 			{DisplayAppNameMap.vscode}
 		</AgentButton>
 	);
@@ -163,7 +161,6 @@ const VSCodeInsidersButton: FC<VSCodeDevContainerButtonProps> = ({
 
 	return (
 		<AgentButton
-			startIcon={<VSCodeInsidersIcon />}
 			disabled={loading}
 			onClick={() => {
 				setLoading(true);
@@ -191,6 +188,7 @@ const VSCodeInsidersButton: FC<VSCodeDevContainerButtonProps> = ({
 					});
 			}}
 		>
+			<VSCodeInsidersIcon />
 			{DisplayAppNameMap.vscode_insiders}
 		</AgentButton>
 	);
diff --git a/site/src/theme/externalImages.ts b/site/src/theme/externalImages.ts
index 889347ea0ec74..22c94b9a44b4b 100644
--- a/site/src/theme/externalImages.ts
+++ b/site/src/theme/externalImages.ts
@@ -1,7 +1,5 @@
 import type { CSSObject } from "@emotion/react";
 
-type ExternalImageMode = keyof ExternalImageModeStyles;
-
 export interface ExternalImageModeStyles {
 	/**
 	 * monochrome icons will be flattened to a neutral, theme-appropriate color.