diff --git a/apps/ui/src/components/dialogs/file-browser-dialog.tsx b/apps/ui/src/components/dialogs/file-browser-dialog.tsx
index 9dae11bb..02552c28 100644
--- a/apps/ui/src/components/dialogs/file-browser-dialog.tsx
+++ b/apps/ui/src/components/dialogs/file-browser-dialog.tsx
@@ -10,8 +10,10 @@ import {
 } from '@/components/ui/dialog';
 import { Button } from '@/components/ui/button';
 import { PathInput } from '@/components/ui/path-input';
+import { Kbd, KbdGroup } from '@/components/ui/kbd';
 import { getJSON, setJSON } from '@/lib/storage';
 import { getDefaultWorkspaceDirectory, saveLastProjectDirectory } from '@/lib/workspace-config';
+import { useOSDetection } from '@/hooks';
 
 interface DirectoryEntry {
   name: string;
@@ -67,6 +69,7 @@ export function FileBrowserDialog({
   description = 'Navigate to your project folder or paste a path directly',
   initialPath,
 }: FileBrowserDialogProps) {
+  const { isMac } = useOSDetection();
   const [currentPath, setCurrentPath] = useState<string>('');
   const [parentPath, setParentPath] = useState<string | null>(null);
   const [directories, setDirectories] = useState<DirectoryEntry[]>([]);
@@ -232,7 +235,7 @@ export function FileBrowserDialog({
 
   return (
     <Dialog open={open} onOpenChange={onOpenChange}>
-      <DialogContent className="bg-popover border-border max-w-3xl max-h-[85vh] overflow-hidden flex flex-col p-4">
+      <DialogContent className="bg-popover border-border max-w-3xl max-h-[85vh] overflow-hidden flex flex-col p-4 focus:outline-none focus-visible:outline-none">
         <DialogHeader className="pb-1">
           <DialogTitle className="flex items-center gap-2 text-base">
             <FolderOpen className="w-4 h-4 text-brand-500" />
@@ -252,6 +255,12 @@ export function FileBrowserDialog({
             error={!!error}
             onNavigate={handleNavigate}
             onHome={handleGoHome}
+            entries={directories.map((dir) => ({ ...dir, isDirectory: true }))}
+            onSelectEntry={(entry) => {
+              if (entry.isDirectory) {
+                handleSelectDirectory(entry);
+              }
+            }}
           />
 
           {/* Recent folders */}
@@ -366,12 +375,10 @@ export function FileBrowserDialog({
           >
             <FolderOpen className="w-3.5 h-3.5 mr-1.5" />
             Select Current Folder
-            <kbd className="ml-2 px-1.5 py-0.5 text-[10px] bg-background/50 rounded border border-border">
-              {typeof navigator !== 'undefined' && navigator.platform?.includes('Mac')
-                ? '⌘'
-                : 'Ctrl'}
-              +↵
-            </kbd>
+            <KbdGroup className="ml-1">
+              <Kbd>{isMac ? '⌘' : 'Ctrl'}</Kbd>
+              <Kbd>↵</Kbd>
+            </KbdGroup>
           </Button>
         </DialogFooter>
       </DialogContent>
diff --git a/apps/ui/src/components/ui/kbd.tsx b/apps/ui/src/components/ui/kbd.tsx
new file mode 100644
index 00000000..670a3872
--- /dev/null
+++ b/apps/ui/src/components/ui/kbd.tsx
@@ -0,0 +1,28 @@
+import { cn } from '@/lib/utils';
+
+function Kbd({ className, ...props }: React.ComponentProps<'kbd'>) {
+  return (
+    <kbd
+      data-slot="kbd"
+      className={cn(
+        'bg-muted text-muted-foreground pointer-events-none inline-flex h-5 w-fit min-w-5 items-center justify-center gap-1 rounded-sm px-1 font-sans text-xs font-medium select-none',
+        "[&_svg:not([class*='size-'])]:size-3",
+        'in-data-[slot=tooltip-content]:bg-background/20 in-data-[slot=tooltip-content]:text-background dark:in-data-[slot=tooltip-content]:bg-background/10',
+        className
+      )}
+      {...props}
+    />
+  );
+}
+
+function KbdGroup({ className, ...props }: React.ComponentProps<'span'>) {
+  return (
+    <span
+      data-slot="kbd-group"
+      className={cn('inline-flex items-center gap-1', className)}
+      {...props}
+    />
+  );
+}
+
+export { Kbd, KbdGroup };
diff --git a/apps/ui/src/components/ui/path-input.tsx b/apps/ui/src/components/ui/path-input.tsx
index 7840c16d..c748d867 100644
--- a/apps/ui/src/components/ui/path-input.tsx
+++ b/apps/ui/src/components/ui/path-input.tsx
@@ -1,8 +1,9 @@
 import { useEffect, Fragment, FocusEvent, KeyboardEvent, MouseEvent } from 'react';
 import { useState, useRef, useCallback, useMemo } from 'react';
-import { Home, ArrowLeft, Pencil, ArrowRight } from 'lucide-react';
+import { Home, ArrowLeft, Pencil, ArrowRight, Search, Folder, File, X } from 'lucide-react';
 import { Button } from '@/components/ui/button';
 import { Input } from '@/components/ui/input';
+import { Kbd } from '@/components/ui/kbd';
 import {
   Breadcrumb,
   BreadcrumbList,
@@ -11,6 +12,14 @@ import {
   BreadcrumbPage,
   BreadcrumbSeparator,
 } from '@/components/ui/breadcrumb';
+import {
+  Command,
+  CommandInput,
+  CommandList,
+  CommandEmpty,
+  CommandGroup,
+  CommandItem,
+} from '@/components/ui/command';
 import { cn } from '@/lib/utils';
 
 interface BreadcrumbSegment {
@@ -52,6 +61,12 @@ function parseBreadcrumbs(path: string): BreadcrumbSegment[] {
   });
 }
 
+interface FileSystemEntry {
+  name: string;
+  path: string;
+  isDirectory: boolean;
+}
+
 interface PathInputProps {
   /** Current resolved path */
   currentPath: string;
@@ -63,12 +78,18 @@ interface PathInputProps {
   error?: boolean;
   /** Placeholder text for the input field */
   placeholder?: string;
+  /** Placeholder text for the search input field */
+  searchPlaceholder?: string;
   /** Called when user navigates to a path (via breadcrumb click, enter key, or navigation buttons) */
   onNavigate: (path: string) => void;
   /** Called when user clicks home button (navigates to home directory) */
   onHome: () => void;
   /** Additional className for the container */
   className?: string;
+  /** List of files and directories in current path for search functionality */
+  entries?: FileSystemEntry[];
+  /** Called when user selects an entry from search results */
+  onSelectEntry?: (entry: FileSystemEntry) => void;
 }
 
 function PathInput({
@@ -77,11 +98,15 @@ function PathInput({
   loading = false,
   error,
   placeholder = 'Paste or type a full path (e.g., /home/user/projects/myapp)',
+  searchPlaceholder = 'Search...',
   onNavigate,
   onHome,
   className,
+  entries = [],
+  onSelectEntry,
 }: PathInputProps) {
   const [isEditing, setIsEditing] = useState(false);
+  const [isSearchOpen, setIsSearchOpen] = useState(false);
   const [pathInput, setPathInput] = useState(currentPath);
   const inputRef = useRef<HTMLInputElement>(null);
   const containerRef = useRef<HTMLDivElement>(null);
@@ -163,6 +188,7 @@ function PathInput({
       // Don't trigger if clicking on a button or already editing
       if (
         isEditing ||
+        isSearchOpen ||
         (e.target as HTMLElement).closest('button') ||
         (e.target as HTMLElement).closest('a')
       ) {
@@ -170,11 +196,79 @@ function PathInput({
       }
       setIsEditing(true);
     },
-    [isEditing]
+    [isEditing, isSearchOpen]
   );
 
+  const handleSelectEntry = useCallback(
+    (entry: FileSystemEntry) => {
+      if (onSelectEntry) {
+        onSelectEntry(entry);
+      }
+      setIsSearchOpen(false);
+    },
+    [onSelectEntry]
+  );
+
+  // Global keyboard shortcut to activate search (/)
+  useEffect(() => {
+    const handleGlobalKeyDown = (e: globalThis.KeyboardEvent) => {
+      // Activate search with '/' key (unless in an input field or contenteditable)
+      if (
+        e.key === '/' &&
+        !isEditing &&
+        !isSearchOpen &&
+        entries.length > 0 &&
+        !(e.target as HTMLElement).matches('input, textarea, [contenteditable="true"]')
+      ) {
+        e.preventDefault();
+        setIsSearchOpen(true);
+      }
+      // Close search with Escape key
+      if (e.key === 'Escape' && isSearchOpen) {
+        e.preventDefault();
+        e.stopPropagation(); // Stop propagation so parent modal doesn't close
+        setIsSearchOpen(false);
+      }
+    };
+
+    // Use capture phase to intercept ESC before parent modal handlers
+    // This allows us to close search first, then let ESC bubble to close modal on second press
+    window.addEventListener('keydown', handleGlobalKeyDown, true);
+    return () => window.removeEventListener('keydown', handleGlobalKeyDown, true);
+  }, [isEditing, isSearchOpen, entries.length]);
+
+  // Close search when clicking outside
+  useEffect(() => {
+    if (!isSearchOpen) return;
+
+    const handleClickOutside = (e: globalThis.MouseEvent) => {
+      const target = e.target as HTMLElement;
+      if (containerRef.current && !containerRef.current.contains(target)) {
+        setIsSearchOpen(false);
+      }
+    };
+
+    document.addEventListener('mousedown', handleClickOutside);
+    return () => document.removeEventListener('mousedown', handleClickOutside);
+  }, [isSearchOpen]);
+
   const breadcrumbs = useMemo(() => parseBreadcrumbs(currentPath), [currentPath]);
 
+  const entryItems = useMemo(
+    () =>
+      entries.map((entry) => (
+        <CommandItem key={entry.path} value={entry.name} onSelect={() => handleSelectEntry(entry)}>
+          {entry.isDirectory ? (
+            <Folder className="w-3.5 h-3.5 text-brand-500 mr-2" />
+          ) : (
+            <File className="w-3.5 h-3.5 text-muted-foreground mr-2" />
+          )}
+          <span className="flex-1 truncate font-mono text-xs">{entry.name}</span>
+        </CommandItem>
+      )),
+    [entries, handleSelectEntry]
+  );
+
   const showBreadcrumbs = currentPath && !isEditing && !loading && !error;
 
   return (
@@ -210,87 +304,139 @@ function PathInput({
       </div>
 
       {/* Path display / input */}
-      <div
-        onClick={handleContainerClick}
-        className={cn(
-          'flex-1 flex items-center gap-2 min-w-0 h-8 px-3 rounded-md border bg-background/50 transition-colors',
-          error
-            ? 'border-destructive focus-within:border-destructive'
-            : 'border-input focus-within:border-ring focus-within:ring-1 focus-within:ring-ring',
-          !isEditing && !error && 'cursor-text hover:border-ring/50'
+      <div className="flex-1 relative min-w-0">
+        {/* Search Popover - positioned to overlap the input */}
+        {isSearchOpen && (
+          <div className="absolute inset-0 z-50">
+            <div className="relative w-full h-full">
+              <div className="absolute inset-0 bg-popover border border-border rounded-md shadow-lg">
+                <Command className="h-auto max-h-[300px]">
+                  <div className="flex items-center gap-2 px-3 **:data-[slot=command-input-wrapper]:border-0 **:data-[slot=command-input-wrapper]:px-0">
+                    <CommandInput
+                      autoFocus
+                      placeholder={searchPlaceholder}
+                      className="h-8 flex-1"
+                    />
+                    <div className="flex items-center gap-1 shrink-0 ml-auto">
+                      <Button
+                        variant="ghost"
+                        size="icon"
+                        onClick={() => setIsSearchOpen(false)}
+                        className="h-6 w-6 text-muted-foreground hover:text-foreground"
+                        aria-label="Close search"
+                      >
+                        <X className="w-3.5 h-3.5" />
+                      </Button>
+                      <Kbd className="hidden py-0.5 sm:inline-block">ESC</Kbd>
+                    </div>
+                  </div>
+                  <CommandList className="scrollbar-styled">
+                    <CommandEmpty>No files or directories found</CommandEmpty>
+                    <CommandGroup>{entryItems}</CommandGroup>
+                  </CommandList>
+                </Command>
+              </div>
+            </div>
+          </div>
         )}
-      >
-        {showBreadcrumbs ? (
-          <>
-            <Breadcrumb className="flex-1 min-w-0 overflow-hidden">
-              <BreadcrumbList className="flex-nowrap overflow-x-auto scrollbar-none">
-                {breadcrumbs.map((crumb) => (
-                  <Fragment key={crumb.path}>
-                    <BreadcrumbItem className="shrink-0">
-                      {crumb.isLast ? (
-                        <BreadcrumbPage className="font-mono text-xs font-medium truncate max-w-[200px]">
-                          {crumb.name}
-                        </BreadcrumbPage>
-                      ) : (
-                        <BreadcrumbLink
-                          href="#"
-                          onClick={(e) => {
-                            e.preventDefault();
-                            handleBreadcrumbClick(crumb.path);
-                          }}
-                          className="font-mono text-xs text-muted-foreground hover:text-foreground transition-colors truncate max-w-[150px]"
-                        >
-                          {crumb.name}
-                        </BreadcrumbLink>
+
+        <div
+          onClick={handleContainerClick}
+          className={cn(
+            'flex items-center gap-2 min-w-0 h-8 px-3 rounded-md border bg-background/50 transition-colors',
+            error
+              ? 'border-destructive focus-within:border-destructive'
+              : 'border-input focus-within:border-ring focus-within:ring-1 focus-within:ring-ring',
+            !isEditing && !error && 'cursor-text hover:border-ring/50'
+          )}
+        >
+          {showBreadcrumbs ? (
+            <>
+              <Breadcrumb className="flex-1 min-w-0 overflow-hidden">
+                <BreadcrumbList className="flex-nowrap overflow-x-auto scrollbar-none">
+                  {breadcrumbs.map((crumb) => (
+                    <Fragment key={crumb.path}>
+                      <BreadcrumbItem className="shrink-0">
+                        {crumb.isLast ? (
+                          <BreadcrumbPage className="font-mono text-xs font-medium truncate max-w-[200px]">
+                            {crumb.name}
+                          </BreadcrumbPage>
+                        ) : (
+                          <BreadcrumbLink
+                            href="#"
+                            onClick={(e) => {
+                              e.preventDefault();
+                              handleBreadcrumbClick(crumb.path);
+                            }}
+                            className="font-mono text-xs text-muted-foreground hover:text-foreground transition-colors truncate max-w-[150px]"
+                          >
+                            {crumb.name}
+                          </BreadcrumbLink>
+                        )}
+                      </BreadcrumbItem>
+                      {!crumb.isLast && (
+                        <BreadcrumbSeparator className="[&>svg]:size-3.5 shrink-0" />
                       )}
-                    </BreadcrumbItem>
-                    {!crumb.isLast && <BreadcrumbSeparator className="[&>svg]:size-3.5 shrink-0" />}
-                  </Fragment>
-                ))}
-              </BreadcrumbList>
-            </Breadcrumb>
-            <Button
-              variant="ghost"
-              size="icon"
-              onClick={handleStartEditing}
-              className="h-6 w-6 shrink-0 text-muted-foreground hover:text-foreground"
-              aria-label="Edit path"
-            >
-              <Pencil className="w-3.5 h-3.5" />
-            </Button>
-          </>
-        ) : (
-          <>
-            <Input
-              ref={inputRef}
-              type="text"
-              placeholder={placeholder}
-              value={pathInput}
-              onChange={(e) => setPathInput(e.target.value)}
-              onKeyDown={handleKeyDown}
-              onBlur={handleInputBlur}
-              className="flex-1 font-mono text-xs h-7 px-0 border-0 shadow-none focus-visible:ring-0 bg-transparent"
-              data-testid="path-input"
-              disabled={loading}
-              aria-label="Path input"
-              aria-invalid={error}
-            />
-            <Button
-              variant="ghost"
-              size="icon"
-              onClick={handleGoToPath}
-              disabled={!pathInput.trim() || loading}
-              className="h-6 w-6 shrink-0"
-              aria-label="Go to path"
-            >
-              <ArrowRight className="w-3.5 h-3.5" />
-            </Button>
-          </>
-        )}
+                    </Fragment>
+                  ))}
+                </BreadcrumbList>
+              </Breadcrumb>
+              <div className="flex items-center gap-0.5 shrink-0">
+                <Button
+                  variant="ghost"
+                  size="icon"
+                  onClick={() => setIsSearchOpen(true)}
+                  className="h-6 w-6 text-muted-foreground hover:text-foreground"
+                  aria-label="Search files and directories"
+                  title="Search files and directories"
+                  disabled={loading || entries.length === 0}
+                >
+                  <Search className="w-3.5 h-3.5" />
+                </Button>
+                <Button
+                  variant="ghost"
+                  size="icon"
+                  onClick={handleStartEditing}
+                  className="h-6 w-6 text-muted-foreground hover:text-foreground"
+                  aria-label="Edit path"
+                >
+                  <Pencil className="w-3.5 h-3.5" />
+                </Button>
+              </div>
+            </>
+          ) : (
+            <>
+              <Input
+                ref={inputRef}
+                type="text"
+                placeholder={placeholder}
+                value={pathInput}
+                onChange={(e) => setPathInput(e.target.value)}
+                onKeyDown={handleKeyDown}
+                onBlur={handleInputBlur}
+                className="flex-1 font-mono text-xs h-7 px-0 border-0 shadow-none focus-visible:ring-0 bg-transparent"
+                data-testid="path-input"
+                disabled={loading}
+                aria-label="Path input"
+                aria-invalid={error}
+              />
+              <Button
+                variant="ghost"
+                size="icon"
+                onClick={handleGoToPath}
+                disabled={!pathInput.trim() || loading}
+                className="h-6 w-6 shrink-0"
+                aria-label="Go to path"
+              >
+                <ArrowRight className="w-3.5 h-3.5" />
+              </Button>
+            </>
+          )}
+        </div>
       </div>
     </div>
   );
 }
 
 export { PathInput, parseBreadcrumbs };
-export type { PathInputProps, BreadcrumbSegment };
+export type { PathInputProps, BreadcrumbSegment, FileSystemEntry };
diff --git a/apps/ui/src/hooks/index.ts b/apps/ui/src/hooks/index.ts
index b18a85e6..8f2264d6 100644
--- a/apps/ui/src/hooks/index.ts
+++ b/apps/ui/src/hooks/index.ts
@@ -3,6 +3,7 @@ export { useBoardBackgroundSettings } from './use-board-background-settings';
 export { useElectronAgent } from './use-electron-agent';
 export { useKeyboardShortcuts } from './use-keyboard-shortcuts';
 export { useMessageQueue } from './use-message-queue';
+export { useOSDetection, type OperatingSystem, type OSDetectionResult } from './use-os-detection';
 export { useResponsiveKanban } from './use-responsive-kanban';
 export { useScrollTracking } from './use-scroll-tracking';
 export { useSettingsMigration } from './use-settings-migration';
diff --git a/apps/ui/src/hooks/use-os-detection.ts b/apps/ui/src/hooks/use-os-detection.ts
new file mode 100644
index 00000000..a7bcf68b
--- /dev/null
+++ b/apps/ui/src/hooks/use-os-detection.ts
@@ -0,0 +1,48 @@
+import { useMemo } from 'react';
+
+export type OperatingSystem = 'mac' | 'windows' | 'linux' | 'unknown';
+
+export interface OSDetectionResult {
+  readonly os: OperatingSystem;
+  readonly isMac: boolean;
+  readonly isWindows: boolean;
+  readonly isLinux: boolean;
+}
+
+function detectOS(): OperatingSystem {
+  // Check Electron's process.platform first (most reliable in Electron apps)
+  if (typeof process !== 'undefined' && process.platform) {
+    if (process.platform === 'darwin') return 'mac';
+    if (process.platform === 'win32') return 'windows';
+    if (process.platform === 'linux') return 'linux';
+  }
+
+  if (typeof navigator === 'undefined') {
+    return 'unknown';
+  }
+
+  // Fallback: use modern userAgentData API with fallback to navigator.platform
+  const nav = navigator as Navigator & { userAgentData?: { platform: string } };
+  const platform = (nav.userAgentData?.platform ?? navigator.platform ?? '').toLowerCase();
+
+  if (platform.includes('mac')) return 'mac';
+  if (platform.includes('win')) return 'windows';
+  if (platform.includes('linux') || platform.includes('x11')) return 'linux';
+  return 'unknown';
+}
+
+/**
+ * Hook to detect the user's operating system.
+ * Returns OS information and convenience boolean flags.
+ */
+export function useOSDetection(): OSDetectionResult {
+  return useMemo(() => {
+    const os = detectOS();
+    return {
+      os,
+      isMac: os === 'mac',
+      isWindows: os === 'windows',
+      isLinux: os === 'linux',
+    };
+  }, []);
+}