diff --git a/frontend/public/locales/en-GB/translation.json b/frontend/public/locales/en-GB/translation.json
index dd6a0ee42..8257ef8c3 100644
--- a/frontend/public/locales/en-GB/translation.json
+++ b/frontend/public/locales/en-GB/translation.json
@@ -66,6 +66,8 @@
   "save": "Save",
   "saveToBrowser": "Save to Browser",
   "download": "Download",
+  "pin": "Pin",
+  "unpin": "Unpin",
   "undoOperationTooltip": "Click to undo the last operation and restore the original files",
   "undo": "Undo",
   "moreOptions": "More Options",
@@ -281,7 +283,8 @@
       "capturing": "Press keys… (Esc to cancel)",
       "change": "Change shortcut",
       "reset": "Reset",
-      "shortcut": "Shortcut"
+      "shortcut": "Shortcut",
+      "noShortcut": "No shortcut set"
     }
   },
   "changeCreds": {
diff --git a/frontend/src/components/fileEditor/FileEditor.module.css b/frontend/src/components/fileEditor/FileEditor.module.css
index 173738c29..17184bbf4 100644
--- a/frontend/src/components/fileEditor/FileEditor.module.css
+++ b/frontend/src/components/fileEditor/FileEditor.module.css
@@ -34,9 +34,9 @@
 .header {
   height: 2.25rem;
   border-radius: 0.0625rem 0.0625rem 0 0;
-  display: grid;
-  grid-template-columns: 44px 1fr 44px;
+  display: flex;
   align-items: center;
+  justify-content: space-between;
   padding: 0 6px;
   user-select: none;
   background: var(--bg-toolbar);
@@ -86,14 +86,23 @@
 }
 
 .headerIndex {
+  position: absolute;
+  left: 50%;
+  transform: translateX(-50%);
   text-align: center;
   font-weight: 500;
   font-size: 18px;
   letter-spacing: 0.04em;
 }
 
-.kebab {
-  justify-self: end;
+.headerActions {
+  display: flex;
+  align-items: center;
+  gap: 8px;
+  margin-left: auto;
+}
+
+.headerIconButton {
   color: #FFFFFF !important;
 }
 
@@ -216,6 +225,11 @@
   color: rgba(0, 0, 0, 0.35);
 }
 
+.pinned {
+  color: #FFC107 !important;
+}
+
+
 /* Unsupported file indicator */
 .unsupportedPill {
   margin-left: 1.75rem;
@@ -384,4 +398,4 @@
 .addFileSubtext {
   font-size: 0.875rem;
   opacity: 0.8;
-}
\ No newline at end of file
+}
diff --git a/frontend/src/components/fileEditor/FileEditor.tsx b/frontend/src/components/fileEditor/FileEditor.tsx
index 626eaab4f..90ee6eebe 100644
--- a/frontend/src/components/fileEditor/FileEditor.tsx
+++ b/frontend/src/components/fileEditor/FileEditor.tsx
@@ -288,7 +288,7 @@ const FileEditor = ({
 
 
   // File operations using context
-  const handleDeleteFile = useCallback((fileId: FileId) => {
+  const handleCloseFile = useCallback((fileId: FileId) => {
     const record = activeStirlingFileStubs.find(r => r.id === fileId);
     const file = record ? selectors.getFile(record.id) : null;
     if (record && file) {
@@ -467,7 +467,7 @@ const FileEditor = ({
                   selectedFiles={localSelectedIds}
                   selectionMode={selectionMode}
                   onToggleFile={toggleFile}
-                  onDeleteFile={handleDeleteFile}
+                  onCloseFile={handleCloseFile}
                   onViewFile={handleViewFile}
                   _onSetStatus={showStatus}
                   onReorderFiles={handleReorderFiles}
diff --git a/frontend/src/components/fileEditor/FileEditorThumbnail.tsx b/frontend/src/components/fileEditor/FileEditorThumbnail.tsx
index f09bfeeb1..8159e30a9 100644
--- a/frontend/src/components/fileEditor/FileEditorThumbnail.tsx
+++ b/frontend/src/components/fileEditor/FileEditorThumbnail.tsx
@@ -1,10 +1,10 @@
 import React, { useState, useCallback, useRef, useMemo, useEffect } from 'react';
-import { Text, ActionIcon, CheckboxIndicator } from '@mantine/core';
+import { Text, ActionIcon, CheckboxIndicator, Tooltip } from '@mantine/core';
 import { alert } from '../toast';
 import { useTranslation } from 'react-i18next';
 import MoreVertIcon from '@mui/icons-material/MoreVert';
 import DownloadOutlinedIcon from '@mui/icons-material/DownloadOutlined';
-import DeleteOutlineIcon from '@mui/icons-material/DeleteOutline';
+import CloseIcon from '@mui/icons-material/Close';
 import UnarchiveIcon from '@mui/icons-material/Unarchive';
 import PushPinIcon from '@mui/icons-material/PushPin';
 import PushPinOutlinedIcon from '@mui/icons-material/PushPinOutlined';
@@ -29,7 +29,7 @@ interface FileEditorThumbnailProps {
   selectedFiles: FileId[];
   selectionMode: boolean;
   onToggleFile: (fileId: FileId) => void;
-  onDeleteFile: (fileId: FileId) => void;
+  onCloseFile: (fileId: FileId) => void;
   onViewFile: (fileId: FileId) => void;
   _onSetStatus: (status: string) => void;
   onReorderFiles?: (sourceFileId: FileId, targetFileId: FileId, selectedFileIds: FileId[]) => void;
@@ -44,7 +44,7 @@ const FileEditorThumbnail = ({
   index,
   selectedFiles,
   onToggleFile,
-  onDeleteFile,
+  onCloseFile,
   _onSetStatus,
   onReorderFiles,
   onDownloadFile,
@@ -258,18 +258,60 @@ const FileEditorThumbnail = ({
           {index + 1}
         </div>
 
-        {/* Kebab menu */}
-        <ActionIcon
-          aria-label={t('moreOptions', 'More options')}
-          variant="subtle"
-          className={styles.kebab}
-          onClick={(e) => {
-            e.stopPropagation();
-            setShowActions((v) => !v);
-          }}
-        >
-          <MoreVertIcon fontSize="small" />
-        </ActionIcon>
+        {/* Action buttons group */}
+        <div className={styles.headerActions}>
+          {/* Pin/Unpin icon */}
+          <Tooltip label={isPinned ? t('unpin', 'Unpin') : t('pin', 'Pin')}>
+            <ActionIcon
+              aria-label={isPinned ? t('unpin', 'Unpin') : t('pin', 'Pin')}
+              variant="subtle"
+              className={isPinned ? styles.pinned : styles.headerIconButton}
+              onClick={(e) => {
+                e.stopPropagation();
+                if (actualFile) {
+                  if (isPinned) {
+                    unpinFile(actualFile);
+                    alert({ alertType: 'neutral', title: `Unpinned ${file.name}`, expandable: false, durationMs: 3000 });
+                  } else {
+                    pinFile(actualFile);
+                    alert({ alertType: 'success', title: `Pinned ${file.name}`, expandable: false, durationMs: 3000 });
+                  }
+                }
+              }}
+            >
+              {isPinned ? <PushPinIcon fontSize="small" /> : <PushPinOutlinedIcon fontSize="small" />}
+            </ActionIcon>
+          </Tooltip>
+
+          {/* Download icon */}
+          <Tooltip label={t('download', 'Download')}>
+            <ActionIcon
+              aria-label={t('download', 'Download')}
+              variant="subtle"
+              className={styles.headerIconButton}
+              onClick={(e) => {
+                e.stopPropagation();
+                onDownloadFile(file.id);
+                alert({ alertType: 'success', title: `Downloading ${file.name}`, expandable: false, durationMs: 2500 });
+              }}
+            >
+              <DownloadOutlinedIcon fontSize="small" />
+            </ActionIcon>
+          </Tooltip>
+
+          {/* Kebab menu */}
+          <ActionIcon
+            aria-label={t('moreOptions', 'More options')}
+            variant="subtle"
+            className={styles.headerIconButton}
+            onClick={(e) => {
+              e.stopPropagation();
+              setShowActions((v) => !v);
+            }}
+          >
+            <MoreVertIcon fontSize="small" />
+          </ActionIcon>
+        </div>
       </div>
 
       {/* Actions overlay */}
@@ -294,7 +336,7 @@ const FileEditorThumbnail = ({
               setShowActions(false);
             }}
           >
-            {isPinned ? <PushPinIcon fontSize="small" /> : <PushPinOutlinedIcon fontSize="small" />}
+            {isPinned ? <PushPinIcon className={styles.pinned} fontSize="small" /> : <PushPinOutlinedIcon fontSize="small" />}
             <span>{isPinned ? t('unpin', 'Unpin') : t('pin', 'Pin')}</span>
           </button>
 
@@ -321,13 +363,13 @@ const FileEditorThumbnail = ({
           <button
             className={`${styles.actionRow} ${styles.actionDanger}`}
             onClick={() => {
-              onDeleteFile(file.id);
-              alert({ alertType: 'neutral', title: `Deleted ${file.name}`, expandable: false, durationMs: 3500 });
+              onCloseFile(file.id);
+              alert({ alertType: 'neutral', title: `Closed ${file.name}`, expandable: false, durationMs: 3500 });
               setShowActions(false);
             }}
           >
-            <DeleteOutlineIcon fontSize="small" />
-            <span>{t('delete', 'Delete')}</span>
+            <CloseIcon fontSize="small" />
+            <span>{t('close', 'Close')}</span>
           </button>
         </div>
       )}
@@ -394,13 +436,6 @@ const FileEditorThumbnail = ({
           )}
         </div>
 
-        {/* Pin indicator (bottom-left) */}
-        {isPinned && (
-          <span className={styles.pinIndicator} aria-hidden>
-            <PushPinIcon fontSize="small" />
-          </span>
-        )}
-
         {/* Drag handle (span wrapper so we can attach a ref reliably) */}
         <span ref={handleRef} className={styles.dragHandle} aria-hidden>
           <DragIndicatorIcon fontSize="small" />
diff --git a/frontend/src/components/hotkeys/HotkeyDisplay.tsx b/frontend/src/components/hotkeys/HotkeyDisplay.tsx
index e240f987e..1b5953a63 100644
--- a/frontend/src/components/hotkeys/HotkeyDisplay.tsx
+++ b/frontend/src/components/hotkeys/HotkeyDisplay.tsx
@@ -55,4 +55,4 @@ export const HotkeyDisplay: React.FC<HotkeyDisplayProps> = ({ binding, size = 's
   );
 };
 
-export default HotkeyDisplay;
\ No newline at end of file
+export default HotkeyDisplay;
diff --git a/frontend/src/components/shared/config/configSections/HotkeysSection.tsx b/frontend/src/components/shared/config/configSections/HotkeysSection.tsx
index e0240f55a..9630d6f05 100644
--- a/frontend/src/components/shared/config/configSections/HotkeysSection.tsx
+++ b/frontend/src/components/shared/config/configSections/HotkeysSection.tsx
@@ -4,7 +4,9 @@ import { useTranslation } from 'react-i18next';
 import { useToolWorkflow } from '../../../../contexts/ToolWorkflowContext';
 import { useHotkeys } from '../../../../contexts/HotkeyContext';
 import HotkeyDisplay from '../../../hotkeys/HotkeyDisplay';
-import { bindingEquals, eventToBinding } from '../../../../utils/hotkeys';
+import { bindingEquals, eventToBinding, HotkeyBinding } from '../../../../utils/hotkeys';
+import { ToolId } from 'src/types/toolId';
+import { ToolRegistryEntry } from 'src/data/toolsTaxonomy';
 
 const rowStyle: React.CSSProperties = {
   display: 'flex',
@@ -24,10 +26,10 @@ const HotkeysSection: React.FC = () => {
   const { t } = useTranslation();
   const { toolRegistry } = useToolWorkflow();
   const { hotkeys, defaults, updateHotkey, resetHotkey, pauseHotkeys, resumeHotkeys, getDisplayParts, isMac } = useHotkeys();
-  const [editingTool, setEditingTool] = useState<string | null>(null);
+  const [editingTool, setEditingTool] = useState<ToolId | null>(null);
   const [error, setError] = useState<string | null>(null);
 
-  const tools = useMemo(() => Object.entries(toolRegistry), [toolRegistry]);
+  const tools = useMemo(() => Object.entries(toolRegistry) as [ToolId, ToolRegistryEntry][], [toolRegistry]);
 
   useEffect(() => {
     if (!editingTool) {
@@ -64,7 +66,7 @@ const HotkeysSection: React.FC = () => {
         return;
       }
 
-      const conflictEntry = Object.entries(hotkeys).find(([toolId, existing]) => (
+      const conflictEntry = (Object.entries(hotkeys) as [ToolId, HotkeyBinding][]).find(([toolId, existing]) => (
         toolId !== editingTool && bindingEquals(existing, binding)
       ));
 
@@ -85,7 +87,7 @@ const HotkeysSection: React.FC = () => {
     };
   }, [editingTool, hotkeys, toolRegistry, updateHotkey, t]);
 
-  const handleStartCapture = (toolId: string) => {
+  const handleStartCapture = (toolId: ToolId) => {
     setEditingTool(toolId);
     setError(null);
   };
@@ -168,4 +170,4 @@ const HotkeysSection: React.FC = () => {
   );
 };
 
-export default HotkeysSection;
\ No newline at end of file
+export default HotkeysSection;
diff --git a/frontend/src/components/tools/SearchResults.tsx b/frontend/src/components/tools/SearchResults.tsx
index 5bd6036cc..aca9f88bc 100644
--- a/frontend/src/components/tools/SearchResults.tsx
+++ b/frontend/src/components/tools/SearchResults.tsx
@@ -7,9 +7,10 @@ import { useToolSections } from '../../hooks/useToolSections';
 import SubcategoryHeader from './shared/SubcategoryHeader';
 import NoToolsFound from './shared/NoToolsFound';
 import "./toolPicker/ToolPicker.css";
+import { ToolId } from 'src/types/toolId';
 
 interface SearchResultsProps {
-  filteredTools: Array<{ item: [string, ToolRegistryEntry]; matchedText?: string }>;
+  filteredTools: Array<{ item: [ToolId, ToolRegistryEntry]; matchedText?: string }>;
   onSelect: (id: string) => void;
   searchQuery?: string;
 }
@@ -40,13 +41,13 @@ const SearchResults: React.FC<SearchResultsProps> = ({ filteredTools, onSelect,
             {group.tools.map(({ id, tool }) => {
               const matchedText = matchedTextMap.get(id);
               // Check if the match was from synonyms and show the actual synonym that matched
-              const isSynonymMatch = matchedText && tool.synonyms?.some(synonym => 
+              const isSynonymMatch = matchedText && tool.synonyms?.some(synonym =>
                 matchedText.toLowerCase().includes(synonym.toLowerCase())
               );
-              const matchedSynonym = isSynonymMatch ? tool.synonyms?.find(synonym => 
+              const matchedSynonym = isSynonymMatch ? tool.synonyms?.find(synonym =>
                 matchedText.toLowerCase().includes(synonym.toLowerCase())
               ) : undefined;
-              
+
               return (
                 <ToolButton
                   key={id}
diff --git a/frontend/src/components/tools/ToolPicker.tsx b/frontend/src/components/tools/ToolPicker.tsx
index 4b0c54536..288a857f3 100644
--- a/frontend/src/components/tools/ToolPicker.tsx
+++ b/frontend/src/components/tools/ToolPicker.tsx
@@ -6,11 +6,12 @@ import "./toolPicker/ToolPicker.css";
 import { useToolSections } from "../../hooks/useToolSections";
 import NoToolsFound from "./shared/NoToolsFound";
 import { renderToolButtons } from "./shared/renderToolButtons";
+import { ToolId } from "src/types/toolId";
 
 interface ToolPickerProps {
   selectedToolKey: string | null;
   onSelect: (id: string) => void;
-  filteredTools: Array<{ item: [string, ToolRegistryEntry]; matchedText?: string }>;
+  filteredTools: Array<{ item: [ToolId, ToolRegistryEntry]; matchedText?: string }>;
   isSearching?: boolean;
 }
 
diff --git a/frontend/src/components/tools/ToolRenderer.tsx b/frontend/src/components/tools/ToolRenderer.tsx
index fbd8100d1..97353ba09 100644
--- a/frontend/src/components/tools/ToolRenderer.tsx
+++ b/frontend/src/components/tools/ToolRenderer.tsx
@@ -2,9 +2,10 @@ import { Suspense } from "react";
 import { useToolWorkflow } from "../../contexts/ToolWorkflowContext";
 import { BaseToolProps } from "../../types/tool";
 import ToolLoadingFallback from "./ToolLoadingFallback";
+import { ToolId } from "src/types/toolId";
 
 interface ToolRendererProps extends BaseToolProps {
-  selectedToolKey: string;
+  selectedToolKey: ToolId;
 }
 
 
diff --git a/frontend/src/components/tools/automate/ToolSelector.tsx b/frontend/src/components/tools/automate/ToolSelector.tsx
index 5cbc4b3ab..02fea2c97 100644
--- a/frontend/src/components/tools/automate/ToolSelector.tsx
+++ b/frontend/src/components/tools/automate/ToolSelector.tsx
@@ -6,6 +6,7 @@ import { useToolSections } from '../../../hooks/useToolSections';
 import { renderToolButtons } from '../shared/renderToolButtons';
 import ToolSearch from '../toolPicker/ToolSearch';
 import ToolButton from '../toolPicker/ToolButton';
+import { ToolId } from 'src/types/toolId';
 
 interface ToolSelectorProps {
   onSelect: (toolKey: string) => void;
@@ -30,7 +31,7 @@ export default function ToolSelector({
 
   // Filter out excluded tools (like 'automate' itself) and tools that don't support automation
   const baseFilteredTools = useMemo(() => {
-    return Object.entries(toolRegistry).filter(([key, tool]) =>
+    return (Object.entries(toolRegistry) as [ToolId, ToolRegistryEntry][]).filter(([key, tool]) =>
       !excludeTools.includes(key) && getToolSupportsAutomate(tool)
     );
   }, [toolRegistry, excludeTools]);
@@ -66,7 +67,7 @@ export default function ToolSelector({
   }, [filteredTools]);
 
   // Use the same tool sections logic as the main ToolPicker
-  const { sections, searchGroups } = useToolSections(transformedFilteredTools);
+  const { sections, searchGroups } = useToolSections(transformedFilteredTools as any /* FIX ME */);
 
   // Determine what to display: search results or organized sections
   const isSearching = searchTerm.trim().length > 0;
@@ -156,7 +157,7 @@ export default function ToolSelector({
           // Show selected tool in AutomationEntry style when tool is selected and dropdown closed
           <div onClick={handleSearchFocus} style={{ cursor: 'pointer',
            borderRadius: "var(--mantine-radius-lg)" }}>
-            <ToolButton id='tool' tool={toolRegistry[selectedValue]}  isSelected={false}
+            <ToolButton id={'tool' as any /* FIX ME */} tool={toolRegistry[selectedValue]}  isSelected={false}
           onSelect={()=>{}} rounded={true} disableNavigation={true}></ToolButton>
           </div>
         ) : (
diff --git a/frontend/src/components/tools/shared/renderToolButtons.tsx b/frontend/src/components/tools/shared/renderToolButtons.tsx
index a4aadf20b..659ffefca 100644
--- a/frontend/src/components/tools/shared/renderToolButtons.tsx
+++ b/frontend/src/components/tools/shared/renderToolButtons.tsx
@@ -5,13 +5,14 @@ import SubcategoryHeader from './SubcategoryHeader';
 import { getSubcategoryLabel } from "../../../data/toolsTaxonomy";
 import { TFunction } from 'i18next';
 import { SubcategoryGroup } from '../../../hooks/useToolSections';
+import { ToolId } from 'src/types/toolId';
 
 // Helper function to render tool buttons for a subcategory
 export const renderToolButtons = (
   t: TFunction,
   subcategory: SubcategoryGroup,
   selectedToolKey: string | null,
-  onSelect: (id: string) => void,
+  onSelect: (id: ToolId) => void,
   showSubcategoryHeader: boolean = true,
   disableNavigation: boolean = false,
   searchResults?: Array<{ item: [string, any]; matchedText?: string }>
@@ -32,7 +33,7 @@ export const renderToolButtons = (
       <div>
         {subcategory.tools.map(({ id, tool }) => {
           const matchedSynonym = matchedTextMap.get(id);
-          
+
           return (
             <ToolButton
               key={id}
diff --git a/frontend/src/components/tools/toolPicker/ToolButton.tsx b/frontend/src/components/tools/toolPicker/ToolButton.tsx
index 467ce6738..8f547e037 100644
--- a/frontend/src/components/tools/toolPicker/ToolButton.tsx
+++ b/frontend/src/components/tools/toolPicker/ToolButton.tsx
@@ -9,12 +9,13 @@ import { handleUnlessSpecialClick } from "../../../utils/clickHandlers";
 import FitText from "../../shared/FitText";
 import { useHotkeys } from "../../../contexts/HotkeyContext";
 import HotkeyDisplay from "../../hotkeys/HotkeyDisplay";
+import { ToolId } from "src/types/toolId";
 
 interface ToolButtonProps {
-  id: string;
+  id: ToolId;
   tool: ToolRegistryEntry;
   isSelected: boolean;
-  onSelect: (id: string) => void;
+  onSelect: (id: ToolId) => void;
   rounded?: boolean;
   disableNavigation?: boolean;
   matchedSynonym?: string;
@@ -28,7 +29,7 @@ const ToolButton: React.FC<ToolButtonProps> = ({ id, tool, isSelected, onSelect,
   const binding = hotkeys[id];
   const { getToolNavigation } = useToolNavigation();
 
-  const handleClick = (id: string) => {
+  const handleClick = (id: ToolId) => {
     if (isUnavailable) return;
     if (tool.link) {
       // Open external link in new tab
@@ -47,12 +48,16 @@ const ToolButton: React.FC<ToolButtonProps> = ({ id, tool, isSelected, onSelect,
     : (
       <div style={{ display: 'flex', flexDirection: 'column', gap: '0.35rem' }}>
         <span>{tool.description}</span>
-        {binding && (
-          <div style={{ display: 'flex', alignItems: 'center', gap: '0.5rem', fontSize: '0.75rem' }}>
+        <div style={{ display: 'flex', alignItems: 'center', gap: '0.5rem', fontSize: '0.75rem' }}>
+        {binding ? (
+          <>
             <span style={{ color: 'var(--mantine-color-dimmed)', fontWeight: 500 }}>{t('settings.hotkeys.shortcut', 'Shortcut')}</span>
             <HotkeyDisplay binding={binding} />
-          </div>
+          </>
+        ) : (
+          <span style={{ color: 'var(--mantine-color-dimmed)', fontWeight: 500, fontStyle: 'italic' }}>{t('settings.hotkeys.noShortcut', 'No shortcut set')}</span>
         )}
+        </div>
       </div>
     );
 
@@ -102,7 +107,7 @@ const ToolButton: React.FC<ToolButtonProps> = ({ id, tool, isSelected, onSelect,
       fullWidth
       justify="flex-start"
       className="tool-button"
-      styles={{ 
+      styles={{
         root: { borderRadius: 0, color: "var(--tools-text-and-icon-color)", overflow: 'visible' },
         label: { overflow: 'visible' }
       }}
@@ -123,7 +128,7 @@ const ToolButton: React.FC<ToolButtonProps> = ({ id, tool, isSelected, onSelect,
       fullWidth
       justify="flex-start"
       className="tool-button"
-      styles={{ 
+      styles={{
         root: { borderRadius: 0, color: "var(--tools-text-and-icon-color)", overflow: 'visible' },
         label: { overflow: 'visible' }
       }}
diff --git a/frontend/src/contexts/HotkeyContext.tsx b/frontend/src/contexts/HotkeyContext.tsx
index fe9cbb600..c5a0f2649 100644
--- a/frontend/src/contexts/HotkeyContext.tsx
+++ b/frontend/src/contexts/HotkeyContext.tsx
@@ -2,14 +2,17 @@ import React, { createContext, useCallback, useContext, useEffect, useMemo, useS
 import { HotkeyBinding, bindingEquals, bindingMatchesEvent, deserializeBindings, getDisplayParts, isMacLike, normalizeBinding, serializeBindings } from '../utils/hotkeys';
 import { useToolWorkflow } from './ToolWorkflowContext';
 import { ToolId } from '../types/toolId';
+import { ToolCategoryId, ToolRegistryEntry } from '../data/toolsTaxonomy';
+
+type Bindings = Partial<Record<ToolId, HotkeyBinding>>;
 
 interface HotkeyContextValue {
-  hotkeys: Record<string, HotkeyBinding>;
-  defaults: Record<string, HotkeyBinding>;
+  hotkeys: Bindings;
+  defaults: Bindings;
   isMac: boolean;
-  updateHotkey: (toolId: string, binding: HotkeyBinding) => void;
-  resetHotkey: (toolId: string) => void;
-  isBindingAvailable: (binding: HotkeyBinding, excludeToolId?: string) => boolean;
+  updateHotkey: (toolId: ToolId, binding: HotkeyBinding) => void;
+  resetHotkey: (toolId: ToolId) => void;
+  isBindingAvailable: (binding: HotkeyBinding, excludeToolId?: ToolId) => boolean;
   pauseHotkeys: () => void;
   resumeHotkeys: () => void;
   areHotkeysPaused: boolean;
@@ -20,46 +23,29 @@ const HotkeyContext = createContext<HotkeyContextValue | undefined>(undefined);
 
 const STORAGE_KEY = 'stirlingpdf.hotkeys';
 
-const KEY_ORDER: string[] = [
-  'Digit1', 'Digit2', 'Digit3', 'Digit4', 'Digit5', 'Digit6', 'Digit7', 'Digit8', 'Digit9', 'Digit0',
-  'KeyQ', 'KeyW', 'KeyE', 'KeyR', 'KeyT', 'KeyY', 'KeyU', 'KeyI', 'KeyO', 'KeyP',
-  'KeyA', 'KeyS', 'KeyD', 'KeyF', 'KeyG', 'KeyH', 'KeyJ', 'KeyK', 'KeyL',
-  'KeyZ', 'KeyX', 'KeyC', 'KeyV', 'KeyB', 'KeyN', 'KeyM',
-  'F1', 'F2', 'F3', 'F4', 'F5', 'F6', 'F7', 'F8', 'F9', 'F10', 'F11', 'F12',
-];
+const generateDefaultHotkeys = (toolEntries: [ToolId, ToolRegistryEntry][], macLike: boolean): Bindings => {
+  const defaults: Bindings = {};
 
-const generateDefaultHotkeys = (toolIds: string[], macLike: boolean): Record<string, HotkeyBinding> => {
-  const defaults: Record<string, HotkeyBinding> = {};
-  let index = 0;
-  let useShift = false;
+  // Get Quick Access tools (RECOMMENDED_TOOLS category) from registry
+  const quickAccessTools = toolEntries
+    .filter(([_, tool]) => tool.categoryId === ToolCategoryId.RECOMMENDED_TOOLS)
+    .map(([toolId, _]) => toolId);
 
-  const nextBinding = (): HotkeyBinding => {
-    if (index >= KEY_ORDER.length) {
-      index = 0;
-      if (!useShift) {
-        useShift = true;
-      } else {
-        // If we somehow run out of combinations, wrap back around (unlikely given tool count)
-        useShift = false;
-      }
+  // Assign Cmd+Option+Number (Mac) or Ctrl+Alt+Number (Windows) to Quick Access tools
+  quickAccessTools.forEach((toolId, index) => {
+    if (index < 9) { // Limit to Digit1-9
+      const digitNumber = index + 1;
+      defaults[toolId] = {
+        code: `Digit${digitNumber}`,
+        alt: true,
+        shift: false,
+        meta: macLike,
+        ctrl: !macLike,
+      };
     }
-
-    const code = KEY_ORDER[index];
-    index += 1;
-
-    return {
-      code,
-      alt: true,
-      shift: useShift,
-      meta: macLike,
-      ctrl: !macLike,
-    };
-  };
-
-  toolIds.forEach(toolId => {
-    defaults[toolId] = nextBinding();
   });
 
+  // All other tools have no default (will be undefined in the record)
   return defaults;
 };
 
@@ -74,7 +60,7 @@ const shouldIgnoreTarget = (target: EventTarget | null): boolean => {
 export const HotkeyProvider: React.FC<{ children: React.ReactNode }> = ({ children }) => {
   const { toolRegistry, handleToolSelect } = useToolWorkflow();
   const isMac = useMemo(() => isMacLike(), []);
-  const [customBindings, setCustomBindings] = useState<Record<string, HotkeyBinding>>(() => {
+  const [customBindings, setCustomBindings] = useState<Bindings>(() => {
     if (typeof window === 'undefined') {
       return {};
     }
@@ -82,16 +68,16 @@ export const HotkeyProvider: React.FC<{ children: React.ReactNode }> = ({ childr
   });
   const [areHotkeysPaused, setHotkeysPaused] = useState(false);
 
-  const toolIds = useMemo(() => Object.keys(toolRegistry), [toolRegistry]);
+  const toolEntries = useMemo(() => Object.entries(toolRegistry), [toolRegistry]) as [ToolId, ToolRegistryEntry][];
 
-  const defaults = useMemo(() => generateDefaultHotkeys(toolIds, isMac), [toolIds, isMac]);
+  const defaults = useMemo(() => generateDefaultHotkeys(toolEntries, isMac), [toolRegistry, isMac]);
 
   // Remove bindings for tools that are no longer present
   useEffect(() => {
     setCustomBindings(prev => {
-      const next: Record<string, HotkeyBinding> = {};
+      const next: Bindings = {};
       let changed = false;
-      Object.entries(prev).forEach(([toolId, binding]) => {
+      (Object.entries(prev) as [ToolId, HotkeyBinding][]).forEach(([toolId, binding]) => {
         if (toolRegistry[toolId]) {
           next[toolId] = binding;
         } else {
@@ -103,13 +89,21 @@ export const HotkeyProvider: React.FC<{ children: React.ReactNode }> = ({ childr
   }, [toolRegistry]);
 
   const resolved = useMemo(() => {
-    const merged: Record<string, HotkeyBinding> = {};
-    toolIds.forEach(toolId => {
+    const merged: Bindings = {};
+    toolEntries.forEach(([toolId, _]) => {
       const custom = customBindings[toolId];
-      merged[toolId] = custom ? normalizeBinding(custom) : defaults[toolId];
+      const defaultBinding = defaults[toolId];
+
+      // Only add to resolved if there's a custom binding or a default binding
+      if (custom) {
+        merged[toolId] = normalizeBinding(custom);
+      } else if (defaultBinding) {
+        merged[toolId] = defaultBinding;
+      }
+      // If neither exists, don't add to merged (tool has no hotkey)
     });
     return merged;
-  }, [customBindings, defaults, toolIds]);
+  }, [customBindings, defaults, toolEntries]);
 
   useEffect(() => {
     if (typeof window === 'undefined') {
@@ -118,7 +112,7 @@ export const HotkeyProvider: React.FC<{ children: React.ReactNode }> = ({ childr
     window.localStorage.setItem(STORAGE_KEY, serializeBindings(customBindings));
   }, [customBindings]);
 
-  const isBindingAvailable = useCallback((binding: HotkeyBinding, excludeToolId?: string) => {
+  const isBindingAvailable = useCallback((binding: HotkeyBinding, excludeToolId?: ToolId) => {
     const normalized = normalizeBinding(binding);
     return Object.entries(resolved).every(([toolId, existing]) => {
       if (toolId === excludeToolId) {
@@ -128,7 +122,7 @@ export const HotkeyProvider: React.FC<{ children: React.ReactNode }> = ({ childr
     });
   }, [resolved]);
 
-  const updateHotkey = useCallback((toolId: string, binding: HotkeyBinding) => {
+  const updateHotkey = useCallback((toolId: ToolId, binding: HotkeyBinding) => {
     setCustomBindings(prev => {
       const normalized = normalizeBinding(binding);
       const defaultsForTool = defaults[toolId];
@@ -142,7 +136,7 @@ export const HotkeyProvider: React.FC<{ children: React.ReactNode }> = ({ childr
     });
   }, [defaults]);
 
-  const resetHotkey = useCallback((toolId: string) => {
+  const resetHotkey = useCallback((toolId: ToolId) => {
     setCustomBindings(prev => {
       if (!(toolId in prev)) {
         return prev;
@@ -165,12 +159,12 @@ export const HotkeyProvider: React.FC<{ children: React.ReactNode }> = ({ childr
       if (event.repeat) return;
       if (shouldIgnoreTarget(event.target)) return;
 
-      const entries = Object.entries(resolved) as Array<[string, HotkeyBinding]>;
+      const entries = Object.entries(resolved) as [ToolId, HotkeyBinding][];
       for (const [toolId, binding] of entries) {
         if (bindingMatchesEvent(binding, event)) {
           event.preventDefault();
           event.stopPropagation();
-          handleToolSelect(toolId as ToolId);
+          handleToolSelect(toolId);
           break;
         }
       }
@@ -208,4 +202,4 @@ export const useHotkeys = (): HotkeyContextValue => {
     throw new Error('useHotkeys must be used within a HotkeyProvider');
   }
   return context;
-};
\ No newline at end of file
+};
diff --git a/frontend/src/contexts/ToolWorkflowContext.tsx b/frontend/src/contexts/ToolWorkflowContext.tsx
index 98a0fd37d..73ef058bf 100644
--- a/frontend/src/contexts/ToolWorkflowContext.tsx
+++ b/frontend/src/contexts/ToolWorkflowContext.tsx
@@ -73,10 +73,10 @@ function toolWorkflowReducer(state: ToolWorkflowState, action: ToolWorkflowActio
 // Context value interface
 interface ToolWorkflowContextValue extends ToolWorkflowState {
   // Tool management (from hook)
-  selectedToolKey: string | null;
+  selectedToolKey: ToolId | null;
   selectedTool: ToolRegistryEntry | null;
-  toolRegistry: Record<string, ToolRegistryEntry>;
-  getSelectedTool: (toolId: string | null) => ToolRegistryEntry | null;
+  toolRegistry: Partial<ToolRegistry>;
+  getSelectedTool: (toolId: ToolId | null) => ToolRegistryEntry | null;
 
   // UI Actions
   setSidebarsVisible: (visible: boolean) => void;
@@ -101,7 +101,7 @@ interface ToolWorkflowContextValue extends ToolWorkflowState {
   handleReaderToggle: () => void;
 
   // Computed values
-  filteredTools: Array<{ item: [string, ToolRegistryEntry]; matchedText?: string }>; // Filtered by search
+  filteredTools: Array<{ item: [ToolId, ToolRegistryEntry]; matchedText?: string }>; // Filtered by search
   isPanelVisible: boolean;
 }
 
diff --git a/frontend/src/data/useTranslatedToolRegistry.tsx b/frontend/src/data/useTranslatedToolRegistry.tsx
index 2c9571e7f..04ac93fa9 100644
--- a/frontend/src/data/useTranslatedToolRegistry.tsx
+++ b/frontend/src/data/useTranslatedToolRegistry.tsx
@@ -828,7 +828,7 @@ export function useFlatToolRegistry(): ToolRegistry {
         name: t("home.compare.title", "Compare"),
         component: null,
         description: t("home.compare.desc", "Compare two PDF documents and highlight differences"),
-        categoryId: ToolCategoryId.RECOMMENDED_TOOLS,
+        categoryId: ToolCategoryId.STANDARD_TOOLS /* TODO: Change to RECOMMENDED_TOOLS when component is implemented */,
         subcategoryId: SubcategoryId.GENERAL,
         synonyms: getSynonyms(t, "compare"),
         supportsAutomate: false,
diff --git a/frontend/src/hooks/useSidebarNavigation.ts b/frontend/src/hooks/useSidebarNavigation.ts
index a65ea96de..42f92e0f1 100644
--- a/frontend/src/hooks/useSidebarNavigation.ts
+++ b/frontend/src/hooks/useSidebarNavigation.ts
@@ -2,6 +2,7 @@ import { useCallback } from 'react';
 import { useToolNavigation } from './useToolNavigation';
 import { useToolWorkflow } from '../contexts/ToolWorkflowContext';
 import { handleUnlessSpecialClick } from '../utils/clickHandlers';
+import { ToolId } from 'src/types/toolId';
 
 export interface SidebarNavigationProps {
   /** Full URL for the navigation (for href attribute) */
@@ -16,7 +17,7 @@ export interface SidebarNavigationProps {
  */
 export function useSidebarNavigation(): {
   getHomeNavigation: () => SidebarNavigationProps;
-  getToolNavigation: (toolId: string) => SidebarNavigationProps | null;
+  getToolNavigation: (toolId: ToolId) => SidebarNavigationProps | null;
 } {
   const { getToolNavigation: getToolNavProps } = useToolNavigation();
   const { getSelectedTool } = useToolWorkflow();
@@ -32,14 +33,14 @@ export function useSidebarNavigation(): {
     return { href, onClick: defaultNavClick };
   }, [defaultNavClick]);
 
-  const getToolNavigation = useCallback((toolId: string): SidebarNavigationProps | null => {
+  const getToolNavigation = useCallback((toolId: ToolId): SidebarNavigationProps | null => {
     // Handle special nav sections that aren't tools
     if (toolId === 'read') return { href: '/read', onClick: defaultNavClick };
     if (toolId === 'automate') return { href: '/automate', onClick: defaultNavClick };
 
     const tool = getSelectedTool(toolId);
     if (!tool) return null;
-    
+
     // Delegate to useToolNavigation for true tools
     return getToolNavProps(toolId, tool);
   }, [getToolNavProps, getSelectedTool, defaultNavClick]);
@@ -48,4 +49,4 @@ export function useSidebarNavigation(): {
     getHomeNavigation,
     getToolNavigation
   };
-}
\ No newline at end of file
+}
diff --git a/frontend/src/hooks/useToolManagement.tsx b/frontend/src/hooks/useToolManagement.tsx
index 3239cbaaa..054e99304 100644
--- a/frontend/src/hooks/useToolManagement.tsx
+++ b/frontend/src/hooks/useToolManagement.tsx
@@ -1,16 +1,17 @@
 import { useState, useCallback, useMemo } from 'react';
 import { useTranslation } from 'react-i18next';
 import { useFlatToolRegistry } from "../data/useTranslatedToolRegistry";
-import { getAllEndpoints, type ToolRegistryEntry } from "../data/toolsTaxonomy";
+import { getAllEndpoints, type ToolRegistryEntry, type ToolRegistry } from "../data/toolsTaxonomy";
 import { useMultipleEndpointsEnabled } from "./useEndpointConfig";
 import { FileId } from '../types/file';
+import { ToolId } from 'src/types/toolId';
 
 interface ToolManagementResult {
   selectedTool: ToolRegistryEntry | null;
   toolSelectedFileIds: FileId[];
-  toolRegistry: Record<string, ToolRegistryEntry>;
+  toolRegistry: Partial<ToolRegistry>;
   setToolSelectedFileIds: (fileIds: FileId[]) => void;
-  getSelectedTool: (toolKey: string | null) => ToolRegistryEntry | null;
+  getSelectedTool: (toolKey: ToolId | null) => ToolRegistryEntry | null;
 }
 
 export const useToolManagement = (): ToolManagementResult => {
@@ -30,9 +31,9 @@ export const useToolManagement = (): ToolManagementResult => {
     return endpoints.length === 0 || endpoints.some((endpoint: string) => endpointStatus[endpoint] === true);
   }, [endpointsLoading, endpointStatus, baseRegistry]);
 
-  const toolRegistry: Record<string, ToolRegistryEntry> = useMemo(() => {
-    const availableToolRegistry: Record<string, ToolRegistryEntry> = {};
-    Object.keys(baseRegistry).forEach(toolKey => {
+  const toolRegistry: Partial<ToolRegistry> = useMemo(() => {
+    const availableToolRegistry: Partial<ToolRegistry> = {};
+    (Object.keys(baseRegistry) as ToolId[]).forEach(toolKey => {
       if (isToolAvailable(toolKey)) {
         const baseTool = baseRegistry[toolKey as keyof typeof baseRegistry];
         availableToolRegistry[toolKey] = {
@@ -45,7 +46,7 @@ export const useToolManagement = (): ToolManagementResult => {
     return availableToolRegistry;
   }, [isToolAvailable, t, baseRegistry]);
 
-  const getSelectedTool = useCallback((toolKey: string | null): ToolRegistryEntry | null => {
+  const getSelectedTool = useCallback((toolKey: ToolId | null): ToolRegistryEntry | null => {
     return toolKey ? toolRegistry[toolKey] || null : null;
   }, [toolRegistry]);
 
diff --git a/frontend/src/hooks/useToolSections.ts b/frontend/src/hooks/useToolSections.ts
index 5c5be8773..40eac31e6 100644
--- a/frontend/src/hooks/useToolSections.ts
+++ b/frontend/src/hooks/useToolSections.ts
@@ -2,9 +2,10 @@ import { useMemo } from 'react';
 
 import { SUBCATEGORY_ORDER, SubcategoryId, ToolCategoryId, ToolRegistryEntry } from '../data/toolsTaxonomy';
 import { useTranslation } from 'react-i18next';
+import { ToolId } from 'src/types/toolId';
 
 type SubcategoryIdMap = {
-  [subcategoryId in SubcategoryId]: Array<{ id: string /* FIX ME: Should be ToolId */; tool: ToolRegistryEntry }>;
+  [subcategoryId in SubcategoryId]: Array<{ id: ToolId; tool: ToolRegistryEntry }>;
 }
 
 type GroupedTools = {
@@ -14,7 +15,7 @@ type GroupedTools = {
 export interface SubcategoryGroup {
   subcategoryId: SubcategoryId;
   tools: {
-    id: string /* FIX ME: Should be ToolId */;
+    id: ToolId;
     tool: ToolRegistryEntry;
   }[];
 };
@@ -28,7 +29,7 @@ export interface ToolSection {
 };
 
 export function useToolSections(
-  filteredTools: Array<{ item: [string /* FIX ME: Should be ToolId */, ToolRegistryEntry]; matchedText?: string }>,
+  filteredTools: Array<{ item: [ToolId, ToolRegistryEntry]; matchedText?: string }>,
   searchQuery?: string
 ) {
   const { t } = useTranslation();
@@ -37,7 +38,7 @@ export function useToolSections(
     if (!filteredTools || !Array.isArray(filteredTools)) {
       return {} as GroupedTools;
     }
-    
+
     const grouped = {} as GroupedTools;
     filteredTools.forEach(({ item: [id, tool] }) => {
       const categoryId = tool.categoryId;
@@ -105,11 +106,11 @@ export function useToolSections(
     if (!filteredTools || !Array.isArray(filteredTools)) {
       return [];
     }
-    
+
     const subMap = {} as SubcategoryIdMap;
-    const seen = new Set<string /* FIX ME: Should be ToolId */>();
+    const seen = new Set<ToolId>();
     filteredTools.forEach(({ item: [id, tool] }) => {
-      const toolId = id as string /* FIX ME: Should be ToolId */;
+      const toolId = id as ToolId;
       if (seen.has(toolId)) return;
       seen.add(toolId);
       const sub = tool.subcategoryId;
diff --git a/frontend/src/utils/toolSearch.ts b/frontend/src/utils/toolSearch.ts
index dda5749a8..8bd963564 100644
--- a/frontend/src/utils/toolSearch.ts
+++ b/frontend/src/utils/toolSearch.ts
@@ -1,8 +1,9 @@
+import { ToolId } from "src/types/toolId";
 import { ToolRegistryEntry } from "../data/toolsTaxonomy";
 import { scoreMatch, minScoreForQuery, normalizeForSearch } from "./fuzzySearch";
 
 export interface RankedToolItem {
-  item: [string, ToolRegistryEntry];
+  item: [ToolId, ToolRegistryEntry];
   matchedText?: string;
 }
 
@@ -10,18 +11,18 @@ export function filterToolRegistryByQuery(
   toolRegistry: Record<string, ToolRegistryEntry>,
   query: string
 ): RankedToolItem[] {
-  const entries = Object.entries(toolRegistry);
+  const entries = Object.entries(toolRegistry) as [ToolId, ToolRegistryEntry][];
   if (!query.trim()) {
-    return entries.map(([id, tool]) => ({ item: [id, tool] as [string, ToolRegistryEntry] }));
+    return entries.map(([id, tool]) => ({ item: [id, tool] as [ToolId, ToolRegistryEntry] }));
   }
 
   const nq = normalizeForSearch(query);
   const threshold = minScoreForQuery(query);
 
-  const exactName: Array<{ id: string; tool: ToolRegistryEntry; pos: number }> = [];
-  const exactSyn: Array<{ id: string; tool: ToolRegistryEntry; text: string; pos: number }> = [];
-  const fuzzyName: Array<{ id: string; tool: ToolRegistryEntry; score: number; text: string }> = [];
-  const fuzzySyn: Array<{ id: string; tool: ToolRegistryEntry; score: number; text: string }> = [];
+  const exactName: Array<{ id: ToolId; tool: ToolRegistryEntry; pos: number }> = [];
+  const exactSyn: Array<{ id: ToolId; tool: ToolRegistryEntry; text: string; pos: number }> = [];
+  const fuzzyName: Array<{ id: ToolId; tool: ToolRegistryEntry; score: number; text: string }> = [];
+  const fuzzySyn: Array<{ id: ToolId; tool: ToolRegistryEntry; score: number; text: string }> = [];
 
   for (const [id, tool] of entries) {
     const nameNorm = normalizeForSearch(tool.name || '');
@@ -78,7 +79,7 @@ export function filterToolRegistryByQuery(
   const seen = new Set<string>();
   const ordered: RankedToolItem[] = [];
 
-  const push = (id: string, tool: ToolRegistryEntry, matchedText?: string) => {
+  const push = (id: ToolId, tool: ToolRegistryEntry, matchedText?: string) => {
     if (seen.has(id)) return;
     seen.add(id);
     ordered.push({ item: [id, tool], matchedText });
@@ -92,7 +93,7 @@ export function filterToolRegistryByQuery(
   if (ordered.length > 0) return ordered;
 
   // Fallback: return everything unchanged
-  return entries.map(([id, tool]) => ({ item: [id, tool] as [string, ToolRegistryEntry] }));
+  return entries.map(([id, tool]) => ({ item: [id, tool] as [ToolId, ToolRegistryEntry] }));
 }