diff --git a/package-lock.json b/package-lock.json
index c83ec7ac..43b48108 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -14,13 +14,18 @@
         "@khanacademy/simple-markdown": "0.8.6",
         "@matrix-org/olm": "3.2.14",
         "@tippyjs/react": "4.2.6",
+        "@vanilla-extract/css": "1.9.3",
+        "@vanilla-extract/recipes": "0.3.0",
+        "@vanilla-extract/vite-plugin": "3.7.1",
         "blurhash": "2.0.4",
         "browser-encrypt-attachment": "0.3.0",
+        "classnames": "2.3.2",
         "dateformat": "5.0.3",
         "emojibase-data": "7.0.1",
         "file-saver": "2.0.5",
         "flux": "4.0.3",
-        "folds": "1.0.2",
+        "focus-trap-react": "10.0.2",
+        "folds": "1.0.4",
         "formik": "2.2.9",
         "html-react-parser": "3.0.4",
         "immer": "9.0.16",
@@ -59,7 +64,7 @@
         "prettier": "2.8.1",
         "sass": "1.56.2",
         "typescript": "4.9.4",
-        "vite": "4.0.1",
+        "vite": "4.0.4",
         "vite-plugin-static-copy": "0.13.0"
       },
       "engines": {
@@ -70,7 +75,6 @@
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-      "dev": true,
       "dependencies": {
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         "@jridgewell/trace-mapping": "^0.3.9"
@@ -83,7 +87,6 @@
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-      "dev": true,
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@@ -92,34 +95,32 @@
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-      "resolved": "https://registry.npmjs.org/@babel/compat-data/-/compat-data-7.20.5.tgz",
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-      "dev": true,
+      "version": "7.20.10",
+      "resolved": "https://registry.npmjs.org/@babel/compat-data/-/compat-data-7.20.10.tgz",
+      "integrity": "sha512-sEnuDPpOJR/fcafHMjpcpGN5M2jbUGUHwmuWKM/YdPzeEDJg8bgmbcWQFUfE32MQjti1koACvoPVsDe8Uq+idg==",
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-      "resolved": "https://registry.npmjs.org/@babel/core/-/core-7.20.5.tgz",
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-      "dev": true,
+      "version": "7.20.12",
+      "resolved": "https://registry.npmjs.org/@babel/core/-/core-7.20.12.tgz",
+      "integrity": "sha512-XsMfHovsUYHFMdrIHkZphTN/2Hzzi78R08NuHfDBehym2VsPDL6Zn/JAD/JQdnRvbSsbQc4mVaU1m6JgtTEElg==",
       "dependencies": {
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-        "@babel/generator": "^7.20.5",
-        "@babel/helper-compilation-targets": "^7.20.0",
-        "@babel/helper-module-transforms": "^7.20.2",
-        "@babel/helpers": "^7.20.5",
-        "@babel/parser": "^7.20.5",
-        "@babel/template": "^7.18.10",
-        "@babel/traverse": "^7.20.5",
-        "@babel/types": "^7.20.5",
+        "@babel/generator": "^7.20.7",
+        "@babel/helper-compilation-targets": "^7.20.7",
+        "@babel/helper-module-transforms": "^7.20.11",
+        "@babel/helpers": "^7.20.7",
+        "@babel/parser": "^7.20.7",
+        "@babel/template": "^7.20.7",
+        "@babel/traverse": "^7.20.12",
+        "@babel/types": "^7.20.7",
         "convert-source-map": "^1.7.0",
         "debug": "^4.1.0",
         "gensync": "^1.0.0-beta.2",
-        "json5": "^2.2.1",
+        "json5": "^2.2.2",
         "semver": "^6.3.0"
       },
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@@ -131,12 +132,11 @@
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-      "resolved": "https://registry.npmjs.org/@babel/generator/-/generator-7.20.5.tgz",
-      "integrity": "sha512-jl7JY2Ykn9S0yj4DQP82sYvPU+T3g0HFcWTqDLqiuA9tGRNIj9VfbtXGAYTTkyNEnQk1jkMGOdYka8aG/lulCA==",
-      "dev": true,
+      "version": "7.20.7",
+      "resolved": "https://registry.npmjs.org/@babel/generator/-/generator-7.20.7.tgz",
+      "integrity": "sha512-7wqMOJq8doJMZmP4ApXTzLxSr7+oO2jroJURrVEp6XShrQUObV8Tq/D0NCcoYg2uHqUrjzO0zwBjoYzelxK+sw==",
       "dependencies": {
-        "@babel/types": "^7.20.5",
+        "@babel/types": "^7.20.7",
         "@jridgewell/gen-mapping": "^0.3.2",
         "jsesc": "^2.5.1"
       },
@@ -148,7 +148,6 @@
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@@ -159,14 +158,14 @@
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-      "resolved": "https://registry.npmjs.org/@babel/helper-compilation-targets/-/helper-compilation-targets-7.20.0.tgz",
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-      "dev": true,
+      "version": "7.20.7",
+      "resolved": "https://registry.npmjs.org/@babel/helper-compilation-targets/-/helper-compilation-targets-7.20.7.tgz",
+      "integrity": "sha512-4tGORmfQcrc+bvrjb5y3dG9Mx1IOZjsHqQVUz7XCNHO+iTmqxWnVg3KRygjGmpRLJGdQSKuvFinbIb0CnZwHAQ==",
       "dependencies": {
-        "@babel/compat-data": "^7.20.0",
+        "@babel/compat-data": "^7.20.5",
         "@babel/helper-validator-option": "^7.18.6",
         "browserslist": "^4.21.3",
+        "lru-cache": "^5.1.1",
         "semver": "^6.3.0"
       },
       "engines": {
@@ -176,11 +175,23 @@
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       }
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+    "node_modules/@babel/helper-compilation-targets/node_modules/lru-cache": {
+      "version": "5.1.1",
+      "resolved": "https://registry.npmjs.org/lru-cache/-/lru-cache-5.1.1.tgz",
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+      "dependencies": {
+        "yallist": "^3.0.2"
+      }
+    },
+    "node_modules/@babel/helper-compilation-targets/node_modules/yallist": {
+      "version": "3.1.1",
+      "resolved": "https://registry.npmjs.org/yallist/-/yallist-3.1.1.tgz",
+      "integrity": "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="
+    },
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@@ -189,7 +200,6 @@
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@@ -202,7 +212,6 @@
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@@ -223,19 +231,18 @@
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-      "resolved": "https://registry.npmjs.org/@babel/helper-module-transforms/-/helper-module-transforms-7.20.2.tgz",
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-      "dev": true,
+      "version": "7.20.11",
+      "resolved": "https://registry.npmjs.org/@babel/helper-module-transforms/-/helper-module-transforms-7.20.11.tgz",
+      "integrity": "sha512-uRy78kN4psmji1s2QtbtcCSaj/LILFDp0f/ymhpQH5QY3nljUZCaNWz9X1dEj/8MBdBEFECs7yRhKn8i7NjZgg==",
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-        "@babel/template": "^7.18.10",
-        "@babel/traverse": "^7.20.1",
-        "@babel/types": "^7.20.2"
+        "@babel/template": "^7.20.7",
+        "@babel/traverse": "^7.20.10",
+        "@babel/types": "^7.20.7"
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@@ -254,7 +260,6 @@
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@@ -278,7 +282,6 @@
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@@ -287,7 +290,6 @@
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@@ -296,20 +298,18 @@
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-      "dev": true,
+      "version": "7.20.13",
+      "resolved": "https://registry.npmjs.org/@babel/helpers/-/helpers-7.20.13.tgz",
+      "integrity": "sha512-nzJ0DWCL3gB5RCXbUO3KIMMsBY2Eqbx8mBpKGE/02PgyRQFcPQLbkQ1vyy596mZLaP+dAfD+R4ckASzNVmW3jg==",
       "dependencies": {
-        "@babel/template": "^7.18.10",
-        "@babel/traverse": "^7.20.5",
-        "@babel/types": "^7.20.5"
+        "@babel/template": "^7.20.7",
+        "@babel/traverse": "^7.20.13",
+        "@babel/types": "^7.20.7"
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@@ -330,10 +329,9 @@
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+      "resolved": "https://registry.npmjs.org/@babel/parser/-/parser-7.20.13.tgz",
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       "bin": {
         "parser": "bin/babel-parser.js"
       },
@@ -341,6 +339,20 @@
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+    "node_modules/@babel/plugin-syntax-typescript": {
+      "version": "7.20.0",
+      "resolved": "https://registry.npmjs.org/@babel/plugin-syntax-typescript/-/plugin-syntax-typescript-7.20.0.tgz",
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+      "dependencies": {
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+      },
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+        "node": ">=6.9.0"
+      },
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+      "resolved": "https://registry.npmjs.org/@babel/template/-/template-7.20.7.tgz",
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-        "@babel/parser": "^7.18.10",
-        "@babel/types": "^7.18.10"
+        "@babel/parser": "^7.20.7",
+        "@babel/types": "^7.20.7"
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-      "dev": true,
+      "version": "7.20.13",
+      "resolved": "https://registry.npmjs.org/@babel/traverse/-/traverse-7.20.13.tgz",
+      "integrity": "sha512-kMJXfF0T6DIS9E8cgdLCSAL+cuCK+YEZHWiLK0SXpTo8YRj5lpJu3CDNKiIBCne4m9hhTIqUg6SYTAI39tAiVQ==",
       "dependencies": {
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-        "@babel/generator": "^7.20.5",
+        "@babel/generator": "^7.20.7",
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-        "@babel/parser": "^7.20.5",
-        "@babel/types": "^7.20.5",
+        "@babel/parser": "^7.20.13",
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@@ -442,10 +452,9 @@
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       "dependencies": {
         "esbuild": "^0.16.3",
@@ -5303,11 +5475,18 @@
       "integrity": "sha512-3wdGidZyq5PB084XLES5TpOSRA3wjXAlIWMhum2kRcv/41Sn2emQ0dycQW4uZXLejwKvg6EsvbdlVL+FYEct7A==",
       "dev": true
     },
+    "node_modules/yaml": {
+      "version": "1.10.2",
+      "resolved": "https://registry.npmjs.org/yaml/-/yaml-1.10.2.tgz",
+      "integrity": "sha512-r3vXyErRCYJ7wg28yvBY5VSoAF8ZvlcW9/BwUzEtUsjvX/DKs24dIkuwjtuprwJJHsbyUbLApepYTR1BN4uHrg==",
+      "engines": {
+        "node": ">= 6"
+      }
+    },
     "node_modules/yocto-queue": {
       "version": "0.1.0",
       "resolved": "https://registry.npmjs.org/yocto-queue/-/yocto-queue-0.1.0.tgz",
       "integrity": "sha512-rVksvsnNCdJ/ohGc6xgPwyN8eheCxsiLM8mxuE/t/mOVqJewPuO1miLpTHQiRgTKCLexL4MeAFVagts7HmNZ2Q==",
-      "dev": true,
       "engines": {
         "node": ">=10"
       },
diff --git a/package.json b/package.json
index 8d90aae3..26ed0add 100644
--- a/package.json
+++ b/package.json
@@ -24,13 +24,18 @@
     "@khanacademy/simple-markdown": "0.8.6",
     "@matrix-org/olm": "3.2.14",
     "@tippyjs/react": "4.2.6",
+    "@vanilla-extract/css": "1.9.3",
+    "@vanilla-extract/recipes": "0.3.0",
+    "@vanilla-extract/vite-plugin": "3.7.1",
     "blurhash": "2.0.4",
     "browser-encrypt-attachment": "0.3.0",
+    "classnames": "2.3.2",
     "dateformat": "5.0.3",
     "emojibase-data": "7.0.1",
     "file-saver": "2.0.5",
     "flux": "4.0.3",
-    "folds": "1.0.2",
+    "focus-trap-react": "10.0.2",
+    "folds": "1.0.4",
     "formik": "2.2.9",
     "html-react-parser": "3.0.4",
     "immer": "9.0.16",
@@ -69,7 +74,7 @@
     "prettier": "2.8.1",
     "sass": "1.56.2",
     "typescript": "4.9.4",
-    "vite": "4.0.1",
+    "vite": "4.0.4",
     "vite-plugin-static-copy": "0.13.0"
   }
 }
diff --git a/src/app/components/sidebar/Sidebar.css.ts b/src/app/components/sidebar/Sidebar.css.ts
new file mode 100644
index 00000000..e62ed6f5
--- /dev/null
+++ b/src/app/components/sidebar/Sidebar.css.ts
@@ -0,0 +1,111 @@
+import { style } from '@vanilla-extract/css';
+import { recipe, RecipeVariants } from '@vanilla-extract/recipes';
+import { color, config, DefaultReset, toRem } from 'folds';
+
+export const Sidebar = style([
+  DefaultReset,
+  {
+    width: toRem(66),
+    backgroundColor: color.Background.Container,
+    borderRight: `${config.borderWidth.B300} solid ${color.Background.ContainerLine}`,
+
+    display: 'flex',
+    flexDirection: 'column',
+    color: color.Background.OnContainer,
+  },
+]);
+
+export const SidebarStack = style([
+  DefaultReset,
+  {
+    width: '100%',
+    display: 'flex',
+    flexDirection: 'column',
+    justifyContent: 'center',
+    alignItems: 'center',
+    gap: config.space.S300,
+    padding: `${config.space.S300} 0`,
+  },
+]);
+
+const PUSH_X = 2;
+export const SidebarAvatarBox = recipe({
+  base: [
+    DefaultReset,
+    {
+      display: 'flex',
+      alignItems: 'center',
+      position: 'relative',
+      transition: 'transform 200ms cubic-bezier(0, 0.8, 0.67, 0.97)',
+
+      selectors: {
+        '&:hover': {
+          transform: `translateX(${toRem(PUSH_X)})`,
+        },
+        '&::before': {
+          content: '',
+          display: 'none',
+          position: 'absolute',
+          left: toRem(-11.5 - PUSH_X),
+          width: toRem(3 + PUSH_X),
+          height: toRem(16),
+          borderRadius: `0 ${toRem(4)} ${toRem(4)} 0`,
+          background: 'CurrentColor',
+          transition: 'height 200ms linear',
+        },
+        '&:hover::before': {
+          display: 'block',
+          width: toRem(3),
+        },
+      },
+    },
+  ],
+  variants: {
+    active: {
+      true: {
+        selectors: {
+          '&::before': {
+            display: 'block',
+            height: toRem(24),
+          },
+          '&:hover::before': {
+            width: toRem(3 + PUSH_X),
+          },
+        },
+      },
+    },
+  },
+});
+
+export type SidebarAvatarBoxVariants = RecipeVariants<typeof SidebarAvatarBox>;
+
+export const SidebarBadgeBox = recipe({
+  base: [
+    DefaultReset,
+    {
+      position: 'absolute',
+      zIndex: 1,
+    },
+  ],
+  variants: {
+    hasCount: {
+      true: {
+        top: toRem(-6),
+        right: toRem(-6),
+      },
+      false: {
+        top: toRem(-2),
+        right: toRem(-2),
+      },
+    },
+  },
+  defaultVariants: {
+    hasCount: false,
+  },
+});
+
+export type SidebarBadgeBoxVariants = RecipeVariants<typeof SidebarBadgeBox>;
+
+export const SidebarBadgeOutline = style({
+  boxShadow: `0 0 0 ${config.borderWidth.B500} ${color.Background.Container}`,
+});
diff --git a/src/app/components/sidebar/Sidebar.tsx b/src/app/components/sidebar/Sidebar.tsx
new file mode 100644
index 00000000..7caf1b21
--- /dev/null
+++ b/src/app/components/sidebar/Sidebar.tsx
@@ -0,0 +1,8 @@
+import classNames from 'classnames';
+import { as } from 'folds';
+import React from 'react';
+import * as css from './Sidebar.css';
+
+export const Sidebar = as<'div'>(({ as: AsSidebar = 'div', className, ...props }, ref) => (
+  <AsSidebar className={classNames(css.Sidebar, className)} {...props} ref={ref} />
+));
diff --git a/src/app/components/sidebar/SidebarAvatar.tsx b/src/app/components/sidebar/SidebarAvatar.tsx
new file mode 100644
index 00000000..8facee35
--- /dev/null
+++ b/src/app/components/sidebar/SidebarAvatar.tsx
@@ -0,0 +1,75 @@
+import classNames from 'classnames';
+import { as, Avatar, Box, color, config, Text, Tooltip, TooltipProvider } from 'folds';
+import React, { forwardRef, MouseEventHandler, ReactNode } from 'react';
+import * as css from './Sidebar.css';
+
+const SidebarAvatarBox = as<'div', css.SidebarAvatarBoxVariants>(
+  ({ as: AsSidebarAvatarBox = 'div', className, active, ...props }, ref) => (
+    <AsSidebarAvatarBox
+      className={classNames(css.SidebarAvatarBox({ active }), className)}
+      {...props}
+      ref={ref}
+    />
+  )
+);
+
+export const SidebarAvatar = forwardRef<
+  HTMLDivElement,
+  css.SidebarAvatarBoxVariants &
+    css.SidebarBadgeBoxVariants & {
+      outlined?: boolean;
+      avatarChildren: ReactNode;
+      tooltip: ReactNode | string;
+      notificationBadge?: (badgeClassName: string) => ReactNode;
+      onClick?: MouseEventHandler<HTMLButtonElement>;
+      onContextMenu?: MouseEventHandler<HTMLButtonElement>;
+    }
+>(
+  (
+    {
+      active,
+      hasCount,
+      outlined,
+      avatarChildren,
+      tooltip,
+      notificationBadge,
+      onClick,
+      onContextMenu,
+    },
+    ref
+  ) => (
+    <SidebarAvatarBox active={active} ref={ref}>
+      <TooltipProvider
+        delay={0}
+        position="right"
+        tooltip={
+          <Tooltip>
+            <Text size="T300">{tooltip}</Text>
+          </Tooltip>
+        }
+      >
+        {(avRef) => (
+          <Avatar
+            ref={avRef}
+            as="button"
+            onClick={onClick}
+            onContextMenu={onContextMenu}
+            style={{
+              border: outlined
+                ? `${config.borderWidth.B300} solid ${color.Background.ContainerLine}`
+                : undefined,
+              cursor: 'pointer',
+            }}
+          >
+            {avatarChildren}
+          </Avatar>
+        )}
+      </TooltipProvider>
+      {notificationBadge && (
+        <Box className={css.SidebarBadgeBox({ hasCount })}>
+          {notificationBadge(css.SidebarBadgeOutline)}
+        </Box>
+      )}
+    </SidebarAvatarBox>
+  )
+);
diff --git a/src/app/components/sidebar/SidebarContent.tsx b/src/app/components/sidebar/SidebarContent.tsx
new file mode 100644
index 00000000..4f405871
--- /dev/null
+++ b/src/app/components/sidebar/SidebarContent.tsx
@@ -0,0 +1,21 @@
+import React, { ReactNode } from 'react';
+import { Box, Scroll } from 'folds';
+
+type SidebarContentProps = {
+  scrollable: ReactNode;
+  sticky: ReactNode;
+};
+export function SidebarContent({ scrollable, sticky }: SidebarContentProps) {
+  return (
+    <>
+      <Box direction="Column" grow="Yes">
+        <Scroll variant="Background" size="0">
+          {scrollable}
+        </Scroll>
+      </Box>
+      <Box direction="Column" shrink="No">
+        {sticky}
+      </Box>
+    </>
+  );
+}
diff --git a/src/app/components/sidebar/SidebarStack.tsx b/src/app/components/sidebar/SidebarStack.tsx
new file mode 100644
index 00000000..c0e976c8
--- /dev/null
+++ b/src/app/components/sidebar/SidebarStack.tsx
@@ -0,0 +1,10 @@
+import React from 'react';
+import classNames from 'classnames';
+import { as } from 'folds';
+import * as css from './Sidebar.css';
+
+export const SidebarStack = as<'div'>(
+  ({ as: AsSidebarStack = 'div', className, ...props }, ref) => (
+    <AsSidebarStack className={classNames(css.SidebarStack, className)} {...props} ref={ref} />
+  )
+);
diff --git a/src/app/components/sidebar/SidebarStackSeparator.tsx b/src/app/components/sidebar/SidebarStackSeparator.tsx
new file mode 100644
index 00000000..110341ca
--- /dev/null
+++ b/src/app/components/sidebar/SidebarStackSeparator.tsx
@@ -0,0 +1,13 @@
+import React from 'react';
+import { Line, toRem } from 'folds';
+
+export function SidebarStackSeparator() {
+  return (
+    <Line
+      role="separator"
+      style={{ width: toRem(24), margin: '0 auto' }}
+      variant="Background"
+      size="300"
+    />
+  );
+}
diff --git a/src/app/components/sidebar/index.ts b/src/app/components/sidebar/index.ts
new file mode 100644
index 00000000..f744628e
--- /dev/null
+++ b/src/app/components/sidebar/index.ts
@@ -0,0 +1,5 @@
+export * from './Sidebar';
+export * from './SidebarAvatar';
+export * from './SidebarContent';
+export * from './SidebarStack';
+export * from './SidebarStackSeparator';
diff --git a/vite.config.js b/vite.config.js
index 38cf8d74..5bd29544 100644
--- a/vite.config.js
+++ b/vite.config.js
@@ -2,6 +2,7 @@ import { defineConfig } from 'vite';
 import react from '@vitejs/plugin-react';
 import { wasm } from '@rollup/plugin-wasm';
 import { viteStaticCopy } from 'vite-plugin-static-copy';
+import { vanillaExtractPlugin } from "@vanilla-extract/vite-plugin";
 
 const copyFiles = {
   targets: [
@@ -33,6 +34,7 @@ export default defineConfig({
   },
   plugins: [
     viteStaticCopy(copyFiles),
+    vanillaExtractPlugin(),
     wasm(),
     react(),
   ],
@@ -41,7 +43,4 @@ export default defineConfig({
     sourcemap: true,
     copyPublicDir: false,
   },
-  optimizeDeps: {
-    include: ["folds"],
-  }
 });