diff --git a/CHANGELOG.md b/CHANGELOG.md
new file mode 100644
index 00000000000..78c591e4d8c
--- /dev/null
+++ b/CHANGELOG.md
@@ -0,0 +1,20 @@
+# Changelog
+
+## [Unreleased]
+
+### Added
+- **Theme selector**: Added theme toggle button in sidebar with three theme options:
+  - **Light**: Light mode
+  - **Dark**: Balanced dark mode with brighter backgrounds and more visible UI elements
+  - **Night**: Darkest mode (previously the only dark mode)
+  - **System**: Follow system preference
+
+### Changed
+- **apps/web/src/hooks/useTheme.ts**: Extended theme system to support `light`, `dark`, `night`, and `system` themes. Added `THEME_OPTIONS` export and `Theme` type export.
+- **apps/web/src/index.css**: Added CSS variables for the new "dark" middle-ground theme and renamed existing dark theme to "night". The dark theme now uses brighter backgrounds (neutral-800/900 vs neutral-950) and more visible borders/accents.
+- **apps/web/src/components/Sidebar.tsx**: Added theme selector menu with icon (Sun/Moon/MoonStar) in the sidebar header, available in both desktop and web modes.
+- **apps/web/src/components/ChatView.tsx**: Made user messages more compact:
+  - Reduced padding (px-3 py-2 instead of px-4 py-3)
+  - Smaller text (13px instead of 14px)
+  - Action buttons (copy, rollback) and timestamp moved below the message card
+  - Actions only appear on hover for cleaner UI
diff --git a/apps/web/src/components/ChatView.tsx b/apps/web/src/components/ChatView.tsx
index c1693f41997..a9340c534ec 100644
--- a/apps/web/src/components/ChatView.tsx
+++ b/apps/web/src/components/ChatView.tsx
@@ -5047,10 +5047,10 @@ const MessagesTimeline = memo(function MessagesTimeline({
           const userImages = row.message.attachments ?? [];
           const canRevertAgentWork = revertTurnCountByUserMessageId.has(row.message.id);
           return (
-            <div className="flex justify-end">
-              <div className="group relative max-w-[80%] rounded-2xl rounded-br-sm border border-border bg-secondary px-4 py-3">
+            <div className="group flex flex-col items-end">
+              <div className="max-w-[80%] rounded-xl rounded-br-sm border border-border bg-secondary px-3 py-2">
                 {userImages.length > 0 && (
-                  <div className="mb-2 grid max-w-[420px] grid-cols-2 gap-2">
+                  <div className="mb-1.5 grid max-w-[420px] grid-cols-2 gap-2">
                     {userImages.map(
                       (image: NonNullable<TimelineMessage["attachments"]>[number]) => (
                         <div
@@ -5087,30 +5087,31 @@ const MessagesTimeline = memo(function MessagesTimeline({
                   </div>
                 )}
                 {row.message.text && (
-                  <pre className="whitespace-pre-wrap wrap-break-word font-mono text-sm leading-relaxed text-foreground">
+                  <pre className="whitespace-pre-wrap wrap-break-word text-[13px] leading-normal text-foreground">
                     {row.message.text}
                   </pre>
                 )}
-                <div className="mt-1.5 flex items-center justify-end gap-2">
-                  <div className="flex items-center gap-1.5 opacity-0 transition-opacity duration-200 focus-within:opacity-100 group-hover:opacity-100">
-                    {row.message.text && <MessageCopyButton text={row.message.text} />}
-                    {canRevertAgentWork && (
-                      <Button
-                        type="button"
-                        size="xs"
-                        variant="outline"
-                        disabled={isRevertingCheckpoint || isWorking}
-                        onClick={() => onRevertUserMessage(row.message.id)}
-                        title="Revert to this message"
-                      >
-                        <Undo2Icon className="size-3" />
-                      </Button>
-                    )}
-                  </div>
-                  <p className="text-right text-[10px] text-muted-foreground/30">
-                    {formatTimestamp(row.message.createdAt)}
-                  </p>
-                </div>
+              </div>
+              <div className="mt-1 flex items-center gap-1.5 opacity-0 transition-opacity duration-200 focus-within:opacity-100 group-hover:opacity-100">
+                {row.message.text && <MessageCopyButton text={row.message.text} />}
+                {canRevertAgentWork && (
+                  <Button
+                    type="button"
+                    size="xs"
+                    variant="outline"
+                    disabled={isRevertingCheckpoint || isWorking}
+                    onClick={() => onRevertUserMessage(row.message.id)}
+                    title="Revert to this message"
+                  >
+                    <Undo2Icon className="size-3" />
+                  </Button>
+                )}
+                <span
+                  className="text-[10px] text-muted-foreground/40"
+                  title={formatTimestamp(row.message.createdAt)}
+                >
+                  {formatTimestamp(row.message.createdAt)}
+                </span>
               </div>
             </div>
           );
diff --git a/apps/web/src/components/Sidebar.tsx b/apps/web/src/components/Sidebar.tsx
index e3a3ce02efb..b4adc6e95d1 100644
--- a/apps/web/src/components/Sidebar.tsx
+++ b/apps/web/src/components/Sidebar.tsx
@@ -2,8 +2,11 @@ import {
   ChevronRightIcon,
   FolderIcon,
   GitPullRequestIcon,
+  MoonIcon,
+  MoonStarIcon,
   RocketIcon,
   SquarePenIcon,
+  SunIcon,
   TerminalIcon,
 } from "lucide-react";
 import { useCallback, useEffect, useMemo, useRef, useState } from "react";
@@ -60,6 +63,14 @@ import {
 } from "./ui/sidebar";
 import { formatWorktreePathForDisplay, getOrphanedWorktreePathForThread } from "../worktreeCleanup";
 import { isNonEmpty as isNonEmptyString } from "effect/String";
+import { useTheme, THEME_OPTIONS, type Theme } from "../hooks/useTheme";
+import {
+  Menu,
+  MenuPopup,
+  MenuRadioGroup,
+  MenuRadioItem,
+  MenuTrigger,
+} from "./ui/menu";
 
 const EMPTY_KEYBINDINGS: ResolvedKeybindingsConfig = [];
 const THREAD_PREVIEW_LIMIT = 6;
@@ -257,7 +268,14 @@ function ProjectFavicon({ cwd }: { cwd: string }) {
   );
 }
 
+function ThemeIcon({ theme }: { theme: Theme }) {
+  if (theme === "light") return <SunIcon className="size-3.5" />;
+  if (theme === "night") return <MoonStarIcon className="size-3.5" />;
+  return <MoonIcon className="size-3.5" />;
+}
+
 export default function Sidebar() {
+  const { theme, setTheme } = useTheme();
   const projects = useStore((store) => store.projects);
   const threads = useStore((store) => store.threads);
   const markThreadUnread = useStore((store) => store.markThreadUnread);
@@ -990,36 +1008,79 @@ export default function Sidebar() {
     </div>
   );
 
+  const themeSelector = (
+    <Menu>
+      <Tooltip>
+        <TooltipTrigger
+          render={
+            <MenuTrigger
+              render={
+                <button
+                  type="button"
+                  aria-label="Change theme"
+                  className="inline-flex size-7 items-center justify-center rounded-md text-muted-foreground transition-colors hover:bg-accent hover:text-foreground"
+                >
+                  <ThemeIcon theme={theme} />
+                </button>
+              }
+            />
+          }
+        />
+        <TooltipPopup side="bottom">Theme</TooltipPopup>
+      </Tooltip>
+      <MenuPopup side="bottom" align="end" className="min-w-[140px]">
+        <MenuRadioGroup
+          value={theme}
+          onValueChange={(value) => setTheme(value as Theme)}
+        >
+          {THEME_OPTIONS.map((option) => (
+            <MenuRadioItem key={option.value} value={option.value}>
+              {option.label}
+            </MenuRadioItem>
+          ))}
+        </MenuRadioGroup>
+      </MenuPopup>
+    </Menu>
+  );
+
   return (
     <>
       {isElectron ? (
         <>
-          <SidebarHeader className="drag-region h-[52px] flex-row items-center gap-2 px-4 py-0 pl-[82px]">
+          <SidebarHeader className="drag-region h-[52px] flex-row items-center gap-1 px-4 py-0 pl-[82px]">
             {wordmark}
-            {showDesktopUpdateButton && (
-              <Tooltip>
-                <TooltipTrigger
-                  render={
-                    <button
-                      type="button"
-                      aria-label={desktopUpdateTooltip}
-                      aria-disabled={desktopUpdateButtonDisabled || undefined}
-                      disabled={desktopUpdateButtonDisabled}
-                      className={`inline-flex size-7 ml-auto mt-2 items-center justify-center rounded-md text-muted-foreground transition-colors ${desktopUpdateButtonInteractivityClasses} ${desktopUpdateButtonClasses}`}
-                      onClick={handleDesktopUpdateButtonClick}
-                    >
-                      <RocketIcon className="size-3.5" />
-                    </button>
-                  }
-                />
-                <TooltipPopup side="bottom">{desktopUpdateTooltip}</TooltipPopup>
-              </Tooltip>
-            )}
+            <div className="ml-auto mt-2 flex items-center gap-0.5">
+              {themeSelector}
+              {showDesktopUpdateButton && (
+                <Tooltip>
+                  <TooltipTrigger
+                    render={
+                      <button
+                        type="button"
+                        aria-label={desktopUpdateTooltip}
+                        aria-disabled={desktopUpdateButtonDisabled || undefined}
+                        disabled={desktopUpdateButtonDisabled}
+                        className={`inline-flex size-7 items-center justify-center rounded-md text-muted-foreground transition-colors ${desktopUpdateButtonInteractivityClasses} ${desktopUpdateButtonClasses}`}
+                        onClick={handleDesktopUpdateButtonClick}
+                      >
+                        <RocketIcon className="size-3.5" />
+                      </button>
+                    }
+                  />
+                  <TooltipPopup side="bottom">{desktopUpdateTooltip}</TooltipPopup>
+                </Tooltip>
+              )}
+            </div>
           </SidebarHeader>
         </>
       ) : (
         <SidebarHeader className="gap-3 px-3 py-2 sm:gap-2.5 sm:px-4 sm:py-3">
-          {wordmark}
+          <div className="flex items-center gap-2">
+            {wordmark}
+            <div className="ml-auto">
+              {themeSelector}
+            </div>
+          </div>
         </SidebarHeader>
       )}
 
diff --git a/apps/web/src/hooks/useTheme.ts b/apps/web/src/hooks/useTheme.ts
index 1e6a7cc8802..715dfc8313d 100644
--- a/apps/web/src/hooks/useTheme.ts
+++ b/apps/web/src/hooks/useTheme.ts
@@ -1,11 +1,18 @@
 import { useCallback, useEffect, useSyncExternalStore } from "react";
 
-type Theme = "light" | "dark" | "system";
+type Theme = "light" | "dark" | "night" | "system";
 type ThemeSnapshot = {
   theme: Theme;
   systemDark: boolean;
 };
 
+export const THEME_OPTIONS = [
+  { value: "light", label: "Light", description: "Light mode" },
+  { value: "dark", label: "Dark", description: "Balanced dark mode" },
+  { value: "night", label: "Night", description: "Darkest mode" },
+  { value: "system", label: "System", description: "Follow system preference" },
+] as const;
+
 const STORAGE_KEY = "t3code:theme";
 const MEDIA_QUERY = "(prefers-color-scheme: dark)";
 
@@ -21,7 +28,7 @@ function getSystemDark(): boolean {
 
 function getStored(): Theme {
   const raw = localStorage.getItem(STORAGE_KEY);
-  if (raw === "light" || raw === "dark" || raw === "system") return raw;
+  if (raw === "light" || raw === "dark" || raw === "night" || raw === "system") return raw;
   return "system";
 }
 
@@ -29,8 +36,22 @@ function applyTheme(theme: Theme, suppressTransitions = false) {
   if (suppressTransitions) {
     document.documentElement.classList.add("no-transitions");
   }
-  const isDark = theme === "dark" || (theme === "system" && getSystemDark());
-  document.documentElement.classList.toggle("dark", isDark);
+  
+  // Determine which CSS classes to apply
+  // - "dark" class = dark mode (middle ground)
+  // - "night" class = darkest mode
+  // - neither = light mode
+  const resolvedTheme = theme === "system" 
+    ? (getSystemDark() ? "dark" : "light") 
+    : theme;
+  
+  document.documentElement.classList.remove("dark", "night");
+  if (resolvedTheme === "dark") {
+    document.documentElement.classList.add("dark");
+  } else if (resolvedTheme === "night") {
+    document.documentElement.classList.add("dark", "night");
+  }
+  
   if (suppressTransitions) {
     // Force a reflow so the no-transitions class takes effect before removal
     // oxlint-disable-next-line no-unused-expressions
@@ -87,8 +108,14 @@ export function useTheme() {
   const snapshot = useSyncExternalStore(subscribe, getSnapshot);
   const theme = snapshot.theme;
 
+  // resolvedTheme returns "light" or "dark" for components that only care about light/dark distinction
+  // (night is treated as dark for icon/color purposes)
   const resolvedTheme: "light" | "dark" =
-    theme === "system" ? (snapshot.systemDark ? "dark" : "light") : theme;
+    theme === "system" 
+      ? (snapshot.systemDark ? "dark" : "light") 
+      : theme === "night" 
+        ? "dark" 
+        : theme;
 
   const setTheme = useCallback((next: Theme) => {
     localStorage.setItem(STORAGE_KEY, next);
@@ -103,3 +130,5 @@ export function useTheme() {
 
   return { theme, setTheme, resolvedTheme } as const;
 }
+
+export type { Theme };
diff --git a/apps/web/src/index.css b/apps/web/src/index.css
index 22817916197..f962a66551c 100644
--- a/apps/web/src/index.css
+++ b/apps/web/src/index.css
@@ -1,6 +1,7 @@
 @import "tailwindcss";
 
 @custom-variant dark (&:is(.dark, .dark *));
+@custom-variant night (&:is(.night, .night *));
 
 @theme inline {
   --animate-skeleton: skeleton 2s -1s infinite linear;
@@ -90,13 +91,44 @@
   --warning: var(--color-amber-500);
   --warning-foreground: var(--color-amber-700);
 
+  /* Dark mode - balanced dark, between light and night */
   @variant dark {
+    color-scheme: dark;
+    --background: color-mix(in srgb, var(--color-neutral-900) 97%, var(--color-black));
+    --foreground: var(--color-neutral-100);
+    --card: color-mix(in srgb, var(--color-neutral-900) 92%, var(--color-white));
+    --card-foreground: var(--color-neutral-100);
+    --popover: color-mix(in srgb, var(--color-neutral-900) 94%, var(--color-white));
+    --popover-foreground: var(--color-neutral-100);
+    --primary: oklch(0.588 0.217 264);
+    --primary-foreground: var(--color-white);
+    --secondary: --alpha(var(--color-white) / 5%);
+    --secondary-foreground: var(--color-neutral-100);
+    --muted: --alpha(var(--color-white) / 6%);
+    --muted-foreground: color-mix(in srgb, var(--color-neutral-400) 90%, var(--color-white));
+    --accent: --alpha(var(--color-white) / 6%);
+    --accent-foreground: var(--color-neutral-100);
+    --destructive: color-mix(in srgb, var(--color-red-500) 90%, var(--color-white));
+    --border: --alpha(var(--color-white) / 8%);
+    --input: --alpha(var(--color-white) / 10%);
+    --ring: oklch(0.588 0.217 264);
+    --destructive-foreground: var(--color-red-400);
+    --info: var(--color-blue-500);
+    --info-foreground: var(--color-blue-400);
+    --success: var(--color-emerald-500);
+    --success-foreground: var(--color-emerald-400);
+    --warning: var(--color-amber-500);
+    --warning-foreground: var(--color-amber-400);
+  }
+
+  /* Night mode - darkest */
+  @variant night {
     color-scheme: dark;
     --background: color-mix(in srgb, var(--color-neutral-950) 95%, var(--color-white));
     --foreground: var(--color-neutral-100);
-    --card: color-mix(in srgb, var(--background) 98%, var(--color-white));
+    --card: color-mix(in srgb, var(--color-neutral-950) 98%, var(--color-white));
     --card-foreground: var(--color-neutral-100);
-    --popover: color-mix(in srgb, var(--background) 98%, var(--color-white));
+    --popover: color-mix(in srgb, var(--color-neutral-950) 98%, var(--color-white));
     --popover-foreground: var(--color-neutral-100);
     --primary: oklch(0.588 0.217 264);
     --primary-foreground: var(--color-white);