diff --git a/apps/x/apps/renderer/src/components/chat-input-with-mentions.tsx b/apps/x/apps/renderer/src/components/chat-input-with-mentions.tsx
index a7d548ea..0254cdfd 100644
--- a/apps/x/apps/renderer/src/components/chat-input-with-mentions.tsx
+++ b/apps/x/apps/renderer/src/components/chat-input-with-mentions.tsx
@@ -1,4 +1,4 @@
-import { useCallback, useEffect, useRef, useState } from 'react'
+import { useCallback, useEffect, useLayoutEffect, useRef, useState } from 'react'
 import { Tooltip, TooltipContent, TooltipTrigger } from '@/components/ui/tooltip'
 import {
   ArrowUp,
@@ -19,6 +19,7 @@ import {
   ImagePlus,
   LoaderIcon,
   Mic,
+  MoreHorizontal,
   Plus,
   ShieldCheck,
   Square,
@@ -29,6 +30,7 @@ import {
 import { Button } from '@/components/ui/button'
 import {
   DropdownMenu,
+  DropdownMenuCheckboxItem,
   DropdownMenuContent,
   DropdownMenuItem,
   DropdownMenuRadioGroup,
@@ -283,6 +285,51 @@ function ChatInputInner({
   const [permissionMode, setPermissionMode] = useState<PermissionMode>('auto')
   const [recentWorkDirs, setRecentWorkDirs] = useState<RecentWorkDir[]>([])
 
+  // Responsive toolbar: measure real overflow and progressively collapse items
+  // right→left until everything fits. Stages:
+  //   1 code→icon · 2 perm→icon · 3 search label hidden · 4 workDir→icon
+  //   5 code→menu · 6 perm→menu · 7 search→menu · 8 workDir→menu
+  // Once items move into the "⋯" overflow menu (≥5) no icon is ever hidden.
+  // overflow-hidden on the left group is the hard guarantee against any overlap.
+  const toolbarRef = useRef<HTMLDivElement>(null)
+  const leftGroupRef = useRef<HTMLDivElement>(null)
+  const lastWidthRef = useRef(0)
+  const [collapseLevel, setCollapseLevel] = useState(0)
+
+  // Re-evaluate from scratch (level 0) whenever the available width changes…
+  useEffect(() => {
+    const outer = toolbarRef.current
+    if (!outer) return
+    const ro = new ResizeObserver(() => {
+      const w = outer.clientWidth
+      if (w !== lastWidthRef.current) {
+        lastWidthRef.current = w
+        setCollapseLevel(0)
+      }
+    })
+    ro.observe(outer)
+    return () => ro.disconnect()
+  }, [])
+
+  // …or when the *set* of items changes (an item appears/disappears, or the model
+  // name width changes). Deliberately excludes the in-place toggles (searchEnabled,
+  // permissionMode, codeModeEnabled, codingAgent): those fire from the overflow menu
+  // for items already inside it, so resetting here would unmount the open menu. The
+  // no-dep effect below still re-collapses if any toggle happens to widen the row.
+  useLayoutEffect(() => {
+    setCollapseLevel(0)
+  }, [workDir, searchAvailable, codeModeFeatureEnabled, lockedModel, activeModelKey])
+
+  // After each render, if the left group still overflows, collapse one more step.
+  // Runs before paint, so the intermediate (overflowing) state is never visible.
+  useLayoutEffect(() => {
+    const el = leftGroupRef.current
+    if (!el) return
+    if (el.scrollWidth > el.clientWidth + 1 && collapseLevel < 8) {
+      setCollapseLevel((l) => Math.min(8, l + 1))
+    }
+  })
+
   // When a run exists, freeze the dropdown to the run's resolved model+provider.
   useEffect(() => {
     if (!runId) {
@@ -757,7 +804,8 @@ function ChatInputInner({
           className="min-h-6 rounded-none border-0 py-0 shadow-none focus-visible:ring-0"
         />
       </div>
-      <div className="flex items-center gap-2 px-4 pb-3">
+      <div ref={toolbarRef} className="flex items-center gap-2 px-4 pb-3">
+        <div ref={leftGroupRef} className="flex min-w-0 items-center gap-2 overflow-hidden">
         <DropdownMenu>
           <Tooltip>
             <TooltipTrigger asChild>
@@ -862,26 +910,32 @@ function ChatInputInner({
             </div>
           </DropdownMenuContent>
         </DropdownMenu>
-        {workDir && (
+        {workDir && collapseLevel < 8 && (
           <Tooltip>
             <TooltipTrigger asChild>
-              <div className="group flex h-7 max-w-[180px] shrink-0 items-center rounded-full border border-border bg-muted/40 pl-2.5 pr-2 text-xs text-muted-foreground transition-colors hover:bg-muted hover:text-foreground">
+              {/* Level 4: collapse to a square icon */}
+              <div className={cn(
+                "group flex h-7 shrink-0 items-center rounded-full border border-border bg-muted/40 text-xs text-muted-foreground transition-colors hover:bg-muted hover:text-foreground",
+                collapseLevel >= 4 ? "w-7 justify-center" : "max-w-[180px] pl-2.5 pr-2"
+              )}>
                 <button
                   type="button"
                   onClick={handleSetWorkDir}
                   className="flex min-w-0 items-center gap-1.5"
                 >
                   <FolderCog className="h-3.5 w-3.5 shrink-0" />
-                  <span className="truncate">{basename(workDir) || workDir}</span>
-                </button>
-                <button
-                  type="button"
-                  onClick={handleClearWorkDir}
-                  aria-label="Remove work directory"
-                  className="flex h-3.5 w-0 shrink-0 items-center justify-center overflow-hidden opacity-0 transition-all duration-150 ease-out hover:text-red-500 group-hover:ml-1 group-hover:w-3.5 group-hover:opacity-100"
-                >
-                  <X className="h-3.5 w-3.5 shrink-0" />
+                  {collapseLevel < 4 && <span className="truncate">{basename(workDir) || workDir}</span>}
                 </button>
+                {collapseLevel < 4 && (
+                  <button
+                    type="button"
+                    onClick={handleClearWorkDir}
+                    aria-label="Remove work directory"
+                    className="flex h-3.5 w-0 shrink-0 items-center justify-center overflow-hidden opacity-0 transition-all duration-150 ease-out hover:text-red-500 group-hover:ml-1 group-hover:w-3.5 group-hover:opacity-100"
+                  >
+                    <X className="h-3.5 w-3.5 shrink-0" />
+                  </button>
+                )}
               </div>
             </TooltipTrigger>
             <TooltipContent side="top">
@@ -889,7 +943,7 @@ function ChatInputInner({
             </TooltipContent>
           </Tooltip>
         )}
-        {searchAvailable && (
+        {searchAvailable && collapseLevel < 7 && (
           <button
             type="button"
             onClick={() => setSearchEnabled((v) => !v)}
@@ -903,16 +957,14 @@ function ChatInputInner({
             )}
           >
             <Globe className="h-4 w-4 shrink-0" />
-            <span
-              className={cn(
-                'overflow-hidden whitespace-nowrap text-xs font-medium transition-all duration-150 ease-out',
-                searchEnabled ? 'ml-1.5 max-w-[60px] opacity-100' : 'max-w-0 opacity-0'
-              )}
-            >
-              Search
-            </span>
+            {searchEnabled && collapseLevel < 3 && (
+              <span className="ml-1.5 whitespace-nowrap text-xs font-medium">
+                Search
+              </span>
+            )}
           </button>
         )}
+        {collapseLevel < 6 && (
         <Tooltip>
           <TooltipTrigger asChild>
             <button
@@ -923,7 +975,8 @@ function ChatInputInner({
               }}
               disabled={Boolean(runId)}
               className={cn(
-                "flex h-7 shrink-0 items-center gap-1.5 rounded-full px-2.5 text-xs font-medium transition-colors",
+                "flex h-7 shrink-0 items-center gap-1.5 rounded-full text-xs font-medium transition-colors",
+                collapseLevel >= 2 ? "w-7 justify-center" : "px-2.5",
                 permissionMode === 'auto'
                   ? "bg-secondary text-foreground hover:bg-secondary/70"
                   : "text-muted-foreground hover:bg-muted hover:text-foreground",
@@ -931,8 +984,8 @@ function ChatInputInner({
               )}
               aria-label="Permission mode"
             >
-              <ShieldCheck className="h-3.5 w-3.5" />
-              <span>{permissionMode === 'auto' ? 'Auto' : 'Manual'}</span>
+              <ShieldCheck className="h-3.5 w-3.5 shrink-0" />
+              {collapseLevel < 2 && <span>{permissionMode === 'auto' ? 'Auto' : 'Manual'}</span>}
             </button>
           </TooltipTrigger>
           <TooltipContent side="top">
@@ -943,37 +996,54 @@ function ChatInputInner({
                 : 'Manual approval prompts — click for auto-permission'}
           </TooltipContent>
         </Tooltip>
-        {codeModeFeatureEnabled && (codeModeEnabled ? (
-          <div className="flex h-7 shrink-0 items-center rounded-full bg-secondary text-xs font-medium text-foreground">
+        )}
+        {codeModeFeatureEnabled && collapseLevel < 5 && (codeModeEnabled ? (
+          collapseLevel >= 1 ? (
+            /* Level 1: collapse the pill to a single icon */
             <Tooltip>
               <TooltipTrigger asChild>
                 <button
                   type="button"
                   onClick={() => setCodeModeEnabled(false)}
-                  className="flex h-full items-center gap-1.5 rounded-l-full pl-2.5 pr-2 transition-colors hover:bg-secondary/70"
+                  className="flex h-7 w-7 shrink-0 items-center justify-center rounded-full bg-secondary text-foreground transition-colors hover:bg-secondary/70"
                 >
                   <Terminal className="h-3.5 w-3.5" />
-                  <span>Code</span>
                 </button>
               </TooltipTrigger>
-              <TooltipContent side="top">Code mode on — click to disable</TooltipContent>
+              <TooltipContent side="top">Code mode on ({codingAgent === 'claude' ? 'Claude Code' : 'Codex'}) — click to disable</TooltipContent>
             </Tooltip>
-            <span className="text-foreground/30">·</span>
-            <Tooltip>
-              <TooltipTrigger asChild>
-                <button
-                  type="button"
-                  onClick={handleToggleCodingAgent}
-                  className="flex h-full items-center rounded-r-full pl-2 pr-2.5 transition-colors hover:bg-secondary/70"
-                >
-                  <span>{codingAgent === 'claude' ? 'Claude' : 'Codex'}</span>
-                </button>
-              </TooltipTrigger>
-              <TooltipContent side="top">
-                Coding agent: {codingAgent === 'claude' ? 'Claude Code' : 'Codex'} — click to swap
-              </TooltipContent>
-            </Tooltip>
-          </div>
+          ) : (
+            <div className="flex h-7 shrink-0 items-center rounded-full bg-secondary text-xs font-medium text-foreground">
+              <Tooltip>
+                <TooltipTrigger asChild>
+                  <button
+                    type="button"
+                    onClick={() => setCodeModeEnabled(false)}
+                    className="flex h-full items-center gap-1.5 rounded-l-full pl-2.5 pr-2 transition-colors hover:bg-secondary/70"
+                  >
+                    <Terminal className="h-3.5 w-3.5" />
+                    <span>Code</span>
+                  </button>
+                </TooltipTrigger>
+                <TooltipContent side="top">Code mode on — click to disable</TooltipContent>
+              </Tooltip>
+              <span className="text-foreground/30">·</span>
+              <Tooltip>
+                <TooltipTrigger asChild>
+                  <button
+                    type="button"
+                    onClick={handleToggleCodingAgent}
+                    className="flex h-full items-center rounded-r-full pl-2 pr-2.5 transition-colors hover:bg-secondary/70"
+                  >
+                    <span>{codingAgent === 'claude' ? 'Claude' : 'Codex'}</span>
+                  </button>
+                </TooltipTrigger>
+                <TooltipContent side="top">
+                  Coding agent: {codingAgent === 'claude' ? 'Claude Code' : 'Codex'} — click to swap
+                </TooltipContent>
+              </Tooltip>
+            </div>
+          )
         ) : (
           <Tooltip>
             <TooltipTrigger asChild>
@@ -989,25 +1059,89 @@ function ChatInputInner({
             <TooltipContent side="top">Use a coding agent (Claude Code or Codex)</TooltipContent>
           </Tooltip>
         ))}
+        </div>
+        {collapseLevel >= 5 && (
+          <DropdownMenu>
+            <Tooltip>
+              <TooltipTrigger asChild>
+                <DropdownMenuTrigger asChild>
+                  <button
+                    type="button"
+                    aria-label="More options"
+                    className="flex h-7 w-7 shrink-0 items-center justify-center rounded-full text-muted-foreground transition-colors hover:bg-muted hover:text-foreground"
+                  >
+                    <MoreHorizontal className="h-4 w-4" />
+                  </button>
+                </DropdownMenuTrigger>
+              </TooltipTrigger>
+              <TooltipContent side="top">More options</TooltipContent>
+            </Tooltip>
+            <DropdownMenuContent align="start" side="top" className="min-w-52">
+              {workDir && collapseLevel >= 8 && (
+                <DropdownMenuItem onSelect={() => { void handleSetWorkDir() }}>
+                  <FolderCog className="size-4" />
+                  <span className="min-w-0 flex-1 truncate">{basename(workDir) || workDir}</span>
+                </DropdownMenuItem>
+              )}
+              {searchAvailable && collapseLevel >= 7 && (
+                <DropdownMenuCheckboxItem
+                  checked={searchEnabled}
+                  onSelect={(e) => e.preventDefault()}
+                  onCheckedChange={(c) => setSearchEnabled(Boolean(c))}
+                >
+                  Web search
+                </DropdownMenuCheckboxItem>
+              )}
+              {collapseLevel >= 6 && (
+                <DropdownMenuCheckboxItem
+                  checked={permissionMode === 'auto'}
+                  disabled={Boolean(runId)}
+                  onSelect={(e) => e.preventDefault()}
+                  onCheckedChange={(c) => setPermissionMode(c ? 'auto' : 'manual')}
+                >
+                  Auto-approve actions
+                </DropdownMenuCheckboxItem>
+              )}
+              {codeModeFeatureEnabled && collapseLevel >= 5 && (
+                <>
+                  <DropdownMenuCheckboxItem
+                    checked={codeModeEnabled}
+                    onSelect={(e) => e.preventDefault()}
+                    onCheckedChange={(c) => setCodeModeEnabled(Boolean(c))}
+                  >
+                    Code mode
+                  </DropdownMenuCheckboxItem>
+                  {codeModeEnabled && (
+                    <DropdownMenuItem onSelect={(e) => { e.preventDefault(); handleToggleCodingAgent() }}>
+                      <Terminal className="size-4" />
+                      <span className="min-w-0 flex-1">Coding agent</span>
+                      <span className="text-xs text-muted-foreground">{codingAgent === 'claude' ? 'Claude' : 'Codex'}</span>
+                    </DropdownMenuItem>
+                  )}
+                </>
+              )}
+            </DropdownMenuContent>
+          </DropdownMenu>
+        )}
         <div className="flex-1" />
         {lockedModel ? (
           <span
-            className="flex h-7 shrink-0 items-center gap-1 rounded-full px-2 text-xs text-muted-foreground"
+            className="flex h-7 min-w-0 items-center gap-1 rounded-full px-2 text-xs text-muted-foreground"
             title={`${providerDisplayNames[lockedModel.provider] || lockedModel.provider} — fixed for this chat`}
           >
-            <span className="max-w-[150px] truncate">{getSelectedModelDisplayName(lockedModel.model)}</span>
+            <span className="min-w-0 truncate">{getSelectedModelDisplayName(lockedModel.model)}</span>
           </span>
         ) : configuredModels.length > 0 ? (
           <DropdownMenu>
             <DropdownMenuTrigger asChild>
               <button
                 type="button"
-                className="flex h-7 shrink-0 items-center gap-1 rounded-full px-2 text-xs text-muted-foreground transition-colors hover:bg-muted hover:text-foreground"
+                className="flex h-7 min-w-0 items-center gap-1 rounded-full px-2 text-xs text-muted-foreground transition-colors hover:bg-muted hover:text-foreground"
               >
-                <span className="max-w-[150px] truncate">
+                <span className="min-w-0 truncate">
                   {getSelectedModelDisplayName(configuredModels.find((m) => `${m.provider}/${m.model}` === activeModelKey)?.model || configuredModels[0]?.model || 'Model')}
                 </span>
-                <ChevronDown className="h-3 w-3" />
+                <ChevronDown className="h-3 w-3 shrink-0" />
               </button>
             </DropdownMenuTrigger>
             <DropdownMenuContent align="end">