diff --git a/frontend/src/core/components/shared/NavigationWarningModal.tsx b/frontend/src/core/components/shared/NavigationWarningModal.tsx
index e87f2fa13..dff9dd957 100644
--- a/frontend/src/core/components/shared/NavigationWarningModal.tsx
+++ b/frontend/src/core/components/shared/NavigationWarningModal.tsx
@@ -1,27 +1,18 @@
 import { Modal, Text, Button, Group, Stack } from "@mantine/core";
-import { useNavigationGuard, useNavigationState } from "@app/contexts/NavigationContext";
+import { useNavigationGuard } from "@app/contexts/NavigationContext";
 import { useTranslation } from "react-i18next";
 import ArrowBackIcon from "@mui/icons-material/ArrowBack";
 import DeleteOutlineIcon from "@mui/icons-material/DeleteOutline";
 import CheckCircleOutlineIcon from "@mui/icons-material/CheckCircleOutline";
-import { useRedactionMode } from "@app/contexts/RedactionContext";
-import FitText from "@app/components/shared/FitText";
 
 interface NavigationWarningModalProps {
   onApplyAndContinue?: () => Promise<void>;
-  onExportAndContinue?: () => Promise<void>;
 }
 
-const NavigationWarningModal = ({ onApplyAndContinue, onExportAndContinue }: NavigationWarningModalProps) => {
+const NavigationWarningModal = ({ onApplyAndContinue }: NavigationWarningModalProps) => {
   const { t } = useTranslation();
   const { showNavigationWarning, hasUnsavedChanges, pendingNavigation, cancelNavigation, confirmNavigation, setHasUnsavedChanges } =
     useNavigationGuard();
-  const { selectedTool } = useNavigationState();
-  const { pendingCount } = useRedactionMode();
-  
-  // Check if we're in redact mode with pending redactions
-  const isRedactMode = selectedTool === 'redact';
-  const hasPendingRedactions = pendingCount > 0;
 
   const handleKeepWorking = () => {
     cancelNavigation();
@@ -40,13 +31,6 @@ const NavigationWarningModal = ({ onApplyAndContinue, onExportAndContinue }: Nav
     confirmNavigation();
   };
 
-  const _handleExportAndContinue = async () => {
-    if (onExportAndContinue) {
-      await onExportAndContinue();
-    }
-    setHasUnsavedChanges(false);
-    confirmNavigation();
-  };
   const BUTTON_WIDTH = "12rem";
 
   // Only show modal if there are unsaved changes AND there's an actual pending navigation
@@ -59,9 +43,7 @@ const NavigationWarningModal = ({ onApplyAndContinue, onExportAndContinue }: Nav
     <Modal
       opened={showNavigationWarning}
       onClose={handleKeepWorking}
-      title={isRedactMode && hasPendingRedactions 
-        ? t("pendingRedactionsTitle", "Unapplied Redactions")
-        : t("unsavedChangesTitle", "Unsaved Changes")}
+      title={t("unsavedChangesTitle", "Unsaved Changes")}
       centered
       size="auto"
       closeOnClickOutside={true}
@@ -70,9 +52,7 @@ const NavigationWarningModal = ({ onApplyAndContinue, onExportAndContinue }: Nav
       <Stack>
         <Stack  ta="center"  p="md">
         <Text size="md" fw="300">
-          {isRedactMode && hasPendingRedactions 
-            ? t("pendingRedactions", "You have unapplied redactions that will be lost.")
-            : t("unsavedChanges", "You have unsaved changes to your PDF.")}
+          {t("unsavedChanges", "You have unsaved changes to your PDF.")}
         </Text>
         <Text size="lg" fw="500" >
           {t("areYouSure", "Are you sure you want to leave?")}
@@ -83,24 +63,16 @@ const NavigationWarningModal = ({ onApplyAndContinue, onExportAndContinue }: Nav
         <Group justify="space-between" gap="xl" visibleFrom="md">
           <Group gap="sm">
             <Button variant="light" color="var(--mantine-color-gray-8)" onClick={handleKeepWorking} w={BUTTON_WIDTH} leftSection={<ArrowBackIcon fontSize="small" />}>
-              <FitText text={t("keepWorking", "Keep Working")} minimumFontScale={0.55} />
+              {t("keepWorking", "Keep Working")}
             </Button>
           </Group>
           <Group gap="sm">
             <Button variant="filled" color="var(--mantine-color-red-9)" onClick={handleDiscardChanges} w={BUTTON_WIDTH} leftSection={<DeleteOutlineIcon fontSize="small" />}>
-              <FitText 
-                text={isRedactMode && hasPendingRedactions 
-                  ? t("discardRedactions", "Discard & Leave")
-                  : t("discardChanges", "Discard & Leave")}
-                minimumFontScale={0.55}
-              />
+              {t("discardChanges", "Discard Changes")}
             </Button>
             {onApplyAndContinue && (
               <Button variant="filled"  onClick={handleApplyAndContinue} w={BUTTON_WIDTH} leftSection={<CheckCircleOutlineIcon fontSize="small" />}>
-                <FitText 
-                  text={t("applyAndContinue", "Save & Leave")}
-                  minimumFontScale={0.55}
-                />
+                {t("applyAndContinue", "Apply & Leave")}
               </Button>
             )}
           </Group>
@@ -109,22 +81,14 @@ const NavigationWarningModal = ({ onApplyAndContinue, onExportAndContinue }: Nav
         {/* Mobile layout: centered stack of 4 buttons */}
         <Stack align="center" gap="sm" hiddenFrom="md">
            <Button variant="light" color="var(--mantine-color-gray-8)"  onClick={handleKeepWorking} w={BUTTON_WIDTH} leftSection={<ArrowBackIcon fontSize="small" />}>
-            <FitText text={t("keepWorking", "Keep Working")} minimumFontScale={0.55} />
+            {t("keepWorking", "Keep Working")}
           </Button>
           <Button variant="filled" color="var(--mantine-color-red-9)" onClick={handleDiscardChanges} w={BUTTON_WIDTH} leftSection={<DeleteOutlineIcon fontSize="small" />}>
-            <FitText 
-              text={isRedactMode && hasPendingRedactions 
-                ? t("discardRedactions", "Discard & Leave")
-                : t("discardChanges", "Discard & Leave")}
-              minimumFontScale={0.55}
-            />
+            {t("discardChanges", "Discard Changes")}
           </Button>
           {onApplyAndContinue && (
             <Button variant="filled" onClick={handleApplyAndContinue} w={BUTTON_WIDTH} leftSection={<CheckCircleOutlineIcon fontSize="small" />}>
-              <FitText 
-                text={t("applyAndContinue", "Save & Leave")}
-                minimumFontScale={0.55}
-              />
+              {t("applyAndContinue", "Apply & Leave")}
             </Button>
           )}
         </Stack>
diff --git a/frontend/src/core/components/shared/rightRail/ViewerAnnotationControls.tsx b/frontend/src/core/components/shared/rightRail/ViewerAnnotationControls.tsx
index f071142a1..74a7d2feb 100644
--- a/frontend/src/core/components/shared/rightRail/ViewerAnnotationControls.tsx
+++ b/frontend/src/core/components/shared/rightRail/ViewerAnnotationControls.tsx
@@ -7,9 +7,7 @@ import { ViewerContext } from '@app/contexts/ViewerContext';
 import { useSignature } from '@app/contexts/SignatureContext';
 import { ColorSwatchButton, ColorPicker } from '@app/components/annotation/shared/ColorPicker';
 import { useFileState, useFileContext } from '@app/contexts/FileContext';
-import { generateThumbnailWithMetadata } from '@app/utils/thumbnailUtils';
-import { createProcessedFile } from '@app/contexts/file/fileActions';
-import { createStirlingFile, createNewStirlingFileStub } from '@app/types/fileContext';
+import { createStirlingFilesAndStubs } from '@app/services/fileStubHelpers';
 import { useNavigationState, useNavigationGuard, useNavigationActions } from '@app/contexts/NavigationContext';
 import { useSidebarContext } from '@app/contexts/SidebarContext';
 import { useToolWorkflow } from '@app/contexts/ToolWorkflowContext';
@@ -50,8 +48,8 @@ export default function ViewerAnnotationControls({ currentView, disabled = false
   
   // Get redaction pending state and navigation guard
   const { pendingCount: redactionPendingCount, isRedacting: _isRedacting } = useRedactionMode();
-  const { requestNavigation } = useNavigationGuard();
-  const { setRedactionMode, activateTextSelection, setRedactionConfig } = useRedaction();
+  const { requestNavigation, setHasUnsavedChanges } = useNavigationGuard();
+  const { setRedactionMode, activateTextSelection, setRedactionConfig, setRedactionsApplied } = useRedaction();
 
   // Turn off annotation mode when switching away from viewer
   useEffect(() => {
@@ -67,37 +65,23 @@ export default function ViewerAnnotationControls({ currentView, disabled = false
 
   // Persist annotations to file if there are unsaved changes
   const saveAnnotationsIfNeeded = async () => {
-    if (!viewerContext?.exportActions?.saveAsCopy || currentView !== 'viewer') return;
-    const hasUnsavedAnnotations = historyApiRef?.current?.canUndo() || false;
-    if (!hasUnsavedAnnotations) return;
+    if (!viewerContext?.exportActions?.saveAsCopy || currentView !== 'viewer' || !historyApiRef?.current?.canUndo()) return;
+    if (activeFiles.length === 0 || state.files.ids.length === 0) return;
 
     try {
-      const pdfArrayBuffer = await viewerContext.exportActions.saveAsCopy();
-      if (!pdfArrayBuffer) return;
+      const arrayBuffer = await viewerContext.exportActions.saveAsCopy();
+      if (!arrayBuffer) return;
 
-      const blob = new Blob([pdfArrayBuffer], { type: 'application/pdf' });
-      const originalFileName = activeFiles.length > 0 ? activeFiles[0].name : 'document.pdf';
-      const newFile = new File([blob], originalFileName, { type: 'application/pdf' });
+      const file = new File([new Blob([arrayBuffer])], activeFiles[0].name, { type: 'application/pdf' });
+      const parentStub = selectors.getStirlingFileStub(state.files.ids[0]);
+      if (!parentStub) return;
 
-      if (activeFiles.length > 0) {
-        const thumbnailResult = await generateThumbnailWithMetadata(newFile);
-        const processedFileMetadata = createProcessedFile(thumbnailResult.pageCount, thumbnailResult.thumbnail);
-
-        const currentFileIds = state.files.ids;
-        if (currentFileIds.length > 0) {
-          const currentFileId = currentFileIds[0];
-          const currentRecord = selectors.getStirlingFileStub(currentFileId);
-          if (!currentRecord) {
-            console.error('No file record found for:', currentFileId);
-            return;
-          }
-
-          const outputStub = createNewStirlingFileStub(newFile, undefined, thumbnailResult.thumbnail, processedFileMetadata);
-          const outputStirlingFile = createStirlingFile(newFile, outputStub.id);
-
-          await fileActions.consumeFiles([currentFileId], [outputStirlingFile], [outputStub]);
-        }
-      }
+      const { stirlingFiles, stubs } = await createStirlingFilesAndStubs([file], parentStub, 'redact');
+      await fileActions.consumeFiles([state.files.ids[0]], stirlingFiles, stubs);
+      
+      // Clear unsaved changes flags after successful save
+      setHasUnsavedChanges(false);
+      setRedactionsApplied(false);
     } catch (error) {
       console.error('Error auto-saving annotations before redaction:', error);
     }
@@ -321,30 +305,20 @@ export default function ViewerAnnotationControls({ currentView, disabled = false
                   const originalFileName = activeFiles.length > 0 ? activeFiles[0].name : 'document.pdf';
                   const newFile = new File([blob], originalFileName, { type: 'application/pdf' });
 
-                  // Replace the current file in context with the saved version (exact same logic as Sign tool)
-                  if (activeFiles.length > 0) {
-                    // Generate thumbnail and metadata for the saved file
-                    const thumbnailResult = await generateThumbnailWithMetadata(newFile);
-                    const processedFileMetadata = createProcessedFile(thumbnailResult.pageCount, thumbnailResult.thumbnail);
-
-                    // Get current file info
-                    const currentFileIds = state.files.ids;
-                    if (currentFileIds.length > 0) {
-                      const currentFileId = currentFileIds[0];
-                      const currentRecord = selectors.getStirlingFileStub(currentFileId);
-
-                      if (!currentRecord) {
-                        console.error('No file record found for:', currentFileId);
-                        return;
-                      }
-
-                      // Create output stub and file (exact same as Sign tool)
-                      const outputStub = createNewStirlingFileStub(newFile, undefined, thumbnailResult.thumbnail, processedFileMetadata);
-                      const outputStirlingFile = createStirlingFile(newFile, outputStub.id);
-
-                      // Replace the original file with the saved version
-                      await fileActions.consumeFiles([currentFileId], [outputStirlingFile], [outputStub]);
+                  // Replace the current file in context with the saved version
+                  if (activeFiles.length > 0 && state.files.ids.length > 0) {
+                    const parentStub = selectors.getStirlingFileStub(state.files.ids[0]);
+                    if (!parentStub) {
+                      console.error('No file record found for:', state.files.ids[0]);
+                      return;
                     }
+
+                    const { stirlingFiles, stubs } = await createStirlingFilesAndStubs([newFile], parentStub, 'multiTool');
+                    await fileActions.consumeFiles([state.files.ids[0]], stirlingFiles, stubs);
+                    
+                    // Clear unsaved changes flags after successful save
+                    setHasUnsavedChanges(false);
+                    setRedactionsApplied(false);
                   }
                 }
               } catch (error) {