diff --git a/frontend/src/core/components/layout/Workbench.tsx b/frontend/src/core/components/layout/Workbench.tsx
index 99d65e83f..0eabada86 100644
--- a/frontend/src/core/components/layout/Workbench.tsx
+++ b/frontend/src/core/components/layout/Workbench.tsx
@@ -3,11 +3,12 @@ import { Box } from '@mantine/core';
 import { useRainbowThemeContext } from '@app/components/shared/RainbowThemeProvider';
 import { useToolWorkflow } from '@app/contexts/ToolWorkflowContext';
 import { useFileHandler } from '@app/hooks/useFileHandler';
-import { useFileState } from '@app/contexts/FileContext';
+import { useFileState, useFileActions } from '@app/contexts/FileContext';
 import { useNavigationState, useNavigationActions, useNavigationGuard } from '@app/contexts/NavigationContext';
 import { isBaseWorkbench } from '@app/types/workbench';
 import { useViewer } from '@app/contexts/ViewerContext';
 import { useAppConfig } from '@app/contexts/AppConfigContext';
+import { FileId } from '@app/types/file';
 import styles from '@app/components/layout/Workbench.module.css';
 
 import TopControls from '@app/components/shared/TopControls';
@@ -26,6 +27,7 @@ export default function Workbench() {
 
   // Use context-based hooks to eliminate all prop drilling
   const { selectors } = useFileState();
+  const { actions: fileActions } = useFileActions();
   const { workbench: currentView } = useNavigationState();
   const { actions: navActions } = useNavigationActions();
   const setCurrentView = navActions.setWorkbench;
@@ -61,13 +63,17 @@ export default function Workbench() {
   const handleFileSelect = useCallback((index: number) => {
     // Don't do anything if selecting the same file
     if (index === activeFileIndex) return;
-    
+
     // requestNavigation handles the unsaved changes check internally
     requestNavigation(() => {
       setActiveFileIndex(index);
     });
   }, [activeFileIndex, requestNavigation, setActiveFileIndex]);
 
+  const handleFileRemove = useCallback(async (fileId: FileId) => {
+    await fileActions.removeFiles([fileId], false); // false = don't delete from IndexedDB, just remove from context
+  }, [fileActions]);
+
   const handlePreviewClose = () => {
     setPreviewFile(null);
     const previousMode = sessionStorage.getItem('previousMode');
@@ -201,6 +207,7 @@ export default function Workbench() {
           })}
           currentFileIndex={activeFileIndex}
           onFileSelect={handleFileSelect}
+          onFileRemove={handleFileRemove}
         />
       )}
 
diff --git a/frontend/src/core/components/shared/FileDropdownMenu.tsx b/frontend/src/core/components/shared/FileDropdownMenu.tsx
index 24583ea77..71942c1bd 100644
--- a/frontend/src/core/components/shared/FileDropdownMenu.tsx
+++ b/frontend/src/core/components/shared/FileDropdownMenu.tsx
@@ -1,15 +1,28 @@
 import React from 'react';
-import { Menu, Loader, Group, Text } from '@mantine/core';
-import VisibilityIcon from '@mui/icons-material/Visibility';
+import { Menu, Loader, Group, Text, ActionIcon, Tooltip } from '@mantine/core';
+import InsertDriveFileIcon from '@mui/icons-material/InsertDriveFile';
 import KeyboardArrowDownIcon from '@mui/icons-material/KeyboardArrowDown';
+import CloseIcon from '@mui/icons-material/Close';
 import FitText from '@app/components/shared/FitText';
 import { PrivateContent } from '@app/components/shared/PrivateContent';
+import { FileId } from '@app/types/file';
+
+// Truncate text from the center: "very-long-filename.pdf" -> "very-lo...ame.pdf"
+function truncateCenter(text: string, maxLength: number = 25): string {
+  if (text.length <= maxLength) return text;
+  const ellipsis = '...';
+  const charsToShow = maxLength - ellipsis.length;
+  const frontChars = Math.ceil(charsToShow / 2);
+  const backChars = Math.floor(charsToShow / 2);
+  return text.substring(0, frontChars) + ellipsis + text.substring(text.length - backChars);
+}
 
 interface FileDropdownMenuProps {
   displayName: string;
   activeFiles: Array<{ fileId: string; name: string; versionNumber?: number }>;
   currentFileIndex: number;
   onFileSelect?: (index: number) => void;
+  onFileRemove?: (fileId: FileId) => void;
   switchingTo?: string | null;
   viewOptionStyle: React.CSSProperties;
   pillRef?: React.RefObject<HTMLDivElement>;
@@ -20,22 +33,27 @@ export const FileDropdownMenu: React.FC<FileDropdownMenuProps> = ({
   activeFiles,
   currentFileIndex,
   onFileSelect,
+  onFileRemove,
   switchingTo,
   viewOptionStyle,
 }) => {
   return (
     <Menu trigger="click" position="bottom" width="30rem">
       <Menu.Target>
-        <div style={{...viewOptionStyle, cursor: 'pointer'}}>
+        <div style={{...viewOptionStyle, cursor: 'pointer', maxWidth: '100%'}}>
           {switchingTo === "viewer" ? (
             <Loader size="xs" />
           ) : (
-            <VisibilityIcon fontSize="small" />
+            <InsertDriveFileIcon fontSize="small" style={{ flexShrink: 0 }} />
           )}
           <PrivateContent>
-            <FitText text={displayName} fontSize={14} minimumFontScale={0.6} />
+            <FitText
+              text={truncateCenter(displayName, 30)}
+              minimumFontScale={0.6}
+              style={{ maxWidth: '12rem', display: 'inline-block' }}
+            />
           </PrivateContent>
-          <KeyboardArrowDownIcon fontSize="small" />
+          <KeyboardArrowDownIcon fontSize="small" style={{ flexShrink: 0 }} />
         </div>
       </Menu.Target>
       <Menu.Dropdown style={{
@@ -65,14 +83,36 @@ export const FileDropdownMenu: React.FC<FileDropdownMenuProps> = ({
               <Group gap="xs" style={{ width: '100%', justifyContent: 'space-between' }}>
                 <div style={{ flex: 1, textAlign: 'left', minWidth: 0 }}>
                   <PrivateContent>
-                    <FitText text={itemName} fontSize={14} minimumFontScale={0.7} />
+                    <FitText
+                      text={truncateCenter(itemName, 50)}
+                      minimumFontScale={0.7}
+                      style={{ display: 'block', width: '100%' }}
+                    />
                   </PrivateContent>
                 </div>
-                {file.versionNumber && file.versionNumber > 1 && (
-                  <Text size="xs" c="dimmed">
-                    v{file.versionNumber}
-                  </Text>
-                )}
+                <Group gap="xs" style={{ flexShrink: 0 }}>
+                  {file.versionNumber && file.versionNumber > 1 && (
+                    <Text size="xs" c="dimmed">
+                      v{file.versionNumber}
+                    </Text>
+                  )}
+                  {onFileRemove && (
+                    <Tooltip label="Close file" withArrow>
+                      <ActionIcon
+                        size="xs"
+                        variant="subtle"
+                        color="red"
+                        onClick={(e) => {
+                          e.stopPropagation();
+                          onFileRemove(file.fileId as FileId);
+                        }}
+                        style={{ flexShrink: 0 }}
+                      >
+                        <CloseIcon style={{ fontSize: 14 }} />
+                      </ActionIcon>
+                    </Tooltip>
+                  )}
+                </Group>
               </Group>
             </Menu.Item>
           );
diff --git a/frontend/src/core/components/shared/PageEditorFileDropdown.tsx b/frontend/src/core/components/shared/PageEditorFileDropdown.tsx
index 161f390df..11f9742c2 100644
--- a/frontend/src/core/components/shared/PageEditorFileDropdown.tsx
+++ b/frontend/src/core/components/shared/PageEditorFileDropdown.tsx
@@ -127,7 +127,7 @@ const FileMenuItem: React.FC<FileMenuItemProps> = ({
           />
           <div style={{ flex: 1, textAlign: 'left', minWidth: 0 }}>
             <PrivateContent>
-              <FitText text={itemName} fontSize={14} minimumFontScale={0.7} />
+              <FitText text={itemName} minimumFontScale={0.7} />
             </PrivateContent>
           </div>
           {file.versionNumber && file.versionNumber > 1 && (
diff --git a/frontend/src/core/components/shared/TopControls.tsx b/frontend/src/core/components/shared/TopControls.tsx
index f414cc91a..e859d70d3 100644
--- a/frontend/src/core/components/shared/TopControls.tsx
+++ b/frontend/src/core/components/shared/TopControls.tsx
@@ -11,6 +11,7 @@ import { PageEditorFileDropdown } from '@app/components/shared/PageEditorFileDro
 import type { CustomWorkbenchViewInstance } from '@app/contexts/ToolWorkflowContext';
 import { FileDropdownMenu } from '@app/components/shared/FileDropdownMenu';
 import { usePageEditorDropdownState, PageEditorDropdownState } from '@app/components/pageEditor/hooks/usePageEditorDropdownState';
+import { FileId } from '@app/types/file';
 
 
 const viewOptionStyle: React.CSSProperties = {
@@ -29,6 +30,7 @@ const createViewOptions = (
   activeFiles: Array<{ fileId: string; name: string; versionNumber?: number }>,
   currentFileIndex: number,
   onFileSelect?: (index: number) => void,
+  onFileRemove?: (fileId: FileId) => void,
   pageEditorState?: PageEditorDropdownState,
   customViews?: CustomWorkbenchViewInstance[]
 ) => {
@@ -37,8 +39,7 @@ const createViewOptions = (
   const isInViewer = currentView === 'viewer';
   const fileName = currentFile?.name || '';
   const viewerDisplayName = isInViewer && fileName ? fileName : 'Viewer';
-  const hasMultipleFiles = activeFiles.length > 1;
-  const showViewerDropdown = isInViewer && hasMultipleFiles;
+  const showViewerDropdown = isInViewer;
 
   const viewerOption = {
     label: showViewerDropdown ? (
@@ -47,6 +48,7 @@ const createViewOptions = (
         activeFiles={activeFiles}
         currentFileIndex={currentFileIndex}
         onFileSelect={onFileSelect}
+        onFileRemove={onFileRemove}
         switchingTo={switchingTo}
         viewOptionStyle={viewOptionStyle}
       />
@@ -132,6 +134,7 @@ interface TopControlsProps {
   activeFiles?: Array<{ fileId: string; name: string; versionNumber?: number }>;
   currentFileIndex?: number;
   onFileSelect?: (index: number) => void;
+  onFileRemove?: (fileId: FileId) => void;
 }
 
 const TopControls = ({
@@ -141,6 +144,7 @@ const TopControls = ({
   activeFiles = [],
   currentFileIndex = 0,
   onFileSelect,
+  onFileRemove,
 }: TopControlsProps) => {
   const { isRainbowMode } = useRainbowThemeContext();
   const [switchingTo, setSwitchingTo] = useState<WorkbenchType | null>(null);
@@ -176,9 +180,10 @@ const TopControls = ({
     activeFiles,
     currentFileIndex,
     onFileSelect,
+    onFileRemove,
     pageEditorState,
     customViews
-  ), [currentView, switchingTo, activeFiles, currentFileIndex, onFileSelect, pageEditorState, customViews]);
+  ), [currentView, switchingTo, activeFiles, currentFileIndex, onFileSelect, onFileRemove, pageEditorState, customViews]);
 
   return (
     <div className="absolute left-0 w-full top-0 z-[100] pointer-events-none">