diff --git a/app/core/src/main/java/stirling/software/SPDF/controller/web/ReactRoutingController.java b/app/core/src/main/java/stirling/software/SPDF/controller/web/ReactRoutingController.java
index 424621b8ad..7741220f24 100644
--- a/app/core/src/main/java/stirling/software/SPDF/controller/web/ReactRoutingController.java
+++ b/app/core/src/main/java/stirling/software/SPDF/controller/web/ReactRoutingController.java
@@ -75,8 +75,7 @@ public class ReactRoutingController {
 
     @GetMapping(
             "/{path:^(?!api|static|robots\\.txt|favicon\\.ico|manifest.*\\.json|pipeline|pdfjs|pdfjs-legacy|fonts|images|files|css|js|assets|locales|modern-logo|classic-logo|Login|og_images|samples)[^\\.]*$}")
-    public ResponseEntity<String> forwardRootPaths(HttpServletRequest request)
-            throws IOException {
+    public ResponseEntity<String> forwardRootPaths(HttpServletRequest request) throws IOException {
         return serveIndexHtml(request);
     }
 
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/SecurityConfiguration.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/SecurityConfiguration.java
index a3a5eee4f0..ab1e4934d8 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/SecurityConfiguration.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/SecurityConfiguration.java
@@ -331,7 +331,9 @@ public class SecurityConfiguration {
                         formLogin ->
                                 formLogin
                                         .loginPage("/login") // Redirect here when unauthenticated
-                                        .loginProcessingUrl("/perform_login") // Process form posts here (not /login)
+                                        .loginProcessingUrl(
+                                                "/perform_login") // Process form posts here (not
+                                        // /login)
                                         .successHandler(
                                                 new CustomAuthenticationSuccessHandler(
                                                         loginAttemptService,
diff --git a/frontend/src/core/hooks/tools/adjustContrast/useAdjustContrastOperation.ts b/frontend/src/core/hooks/tools/adjustContrast/useAdjustContrastOperation.ts
index 176ddd4b5f..6524a2585d 100644
--- a/frontend/src/core/hooks/tools/adjustContrast/useAdjustContrastOperation.ts
+++ b/frontend/src/core/hooks/tools/adjustContrast/useAdjustContrastOperation.ts
@@ -1,5 +1,5 @@
 import { useTranslation } from 'react-i18next';
-import { ToolType, useToolOperation } from '@app/hooks/tools/shared/useToolOperation';
+import { ToolType, useToolOperation, CustomProcessorResult } from '@app/hooks/tools/shared/useToolOperation';
 import { AdjustContrastParameters, defaultParameters } from '@app/hooks/tools/adjustContrast/useAdjustContrastParameters';
 import { PDFDocument as PDFLibDocument } from 'pdf-lib';
 import { applyAdjustmentsToCanvas } from '@app/components/tools/adjustContrast/utils';
@@ -46,7 +46,7 @@ async function buildAdjustedPdfForFile(file: File, params: AdjustContrastParamet
     return out;
 }
 
-async function processPdfClientSide(params: AdjustContrastParameters, files: File[]): Promise<File[]> {
+async function processPdfClientSide(params: AdjustContrastParameters, files: File[]): Promise<CustomProcessorResult> {
   // Limit concurrency to avoid exhausting memory/CPU while still getting speedups
   // Heuristic: use up to 4 workers on capable machines, otherwise 2-3
   let CONCURRENCY_LIMIT = 2;
@@ -72,7 +72,12 @@ async function processPdfClientSide(params: AdjustContrastParameters, files: Fil
     return results;
   };
 
-  return mapWithConcurrency(files, CONCURRENCY_LIMIT, (file) => buildAdjustedPdfForFile(file, params));
+  const processedFiles = await mapWithConcurrency(files, CONCURRENCY_LIMIT, (file) => buildAdjustedPdfForFile(file, params));
+
+  return {
+    files: processedFiles,
+    consumedAllInputs: false,
+  };
 }
 
 export const adjustContrastOperationConfig = {
diff --git a/frontend/src/core/hooks/tools/automate/useAutomateOperation.ts b/frontend/src/core/hooks/tools/automate/useAutomateOperation.ts
index 004f289027..f6fbcacda7 100644
--- a/frontend/src/core/hooks/tools/automate/useAutomateOperation.ts
+++ b/frontend/src/core/hooks/tools/automate/useAutomateOperation.ts
@@ -36,7 +36,10 @@ export function useAutomateOperation() {
     );
 
     console.log(`✅ Automation completed, returning ${finalResults.length} files`);
-    return finalResults;
+    return {
+      files: finalResults,
+      consumedAllInputs: false,
+    };
   }, [toolRegistry]);
 
   return useToolOperation<AutomateParameters>({
diff --git a/frontend/src/core/hooks/tools/convert/useConvertOperation.ts b/frontend/src/core/hooks/tools/convert/useConvertOperation.ts
index 9134c9db4a..9650ac0e2a 100644
--- a/frontend/src/core/hooks/tools/convert/useConvertOperation.ts
+++ b/frontend/src/core/hooks/tools/convert/useConvertOperation.ts
@@ -3,8 +3,8 @@ import apiClient from '@app/services/apiClient';
 import { useTranslation } from 'react-i18next';
 import { ConvertParameters, defaultParameters } from '@app/hooks/tools/convert/useConvertParameters';
 import { createFileFromApiResponse } from '@app/utils/fileResponseUtils';
-import { useToolOperation, ToolType } from '@app/hooks/tools/shared/useToolOperation';
-import { getEndpointUrl, isImageFormat, isWebFormat } from '@app/utils/convertUtils';
+import { useToolOperation, ToolType, CustomProcessorResult } from '@app/hooks/tools/shared/useToolOperation';
+import { getEndpointUrl, isImageFormat, isWebFormat, isOfficeFormat } from '@app/utils/convertUtils';
 
 // Static function that can be used by both the hook and automation executor
 export const shouldProcessFilesSeparately = (
@@ -21,6 +21,10 @@ export const shouldProcessFilesSeparately = (
     (parameters.fromExtension === 'pdf' && parameters.toExtension === 'pdfa') ||
     // PDF to text-like formats should be one output per input
     (parameters.fromExtension === 'pdf' && ['txt', 'rtf', 'csv'].includes(parameters.toExtension)) ||
+    // PDF to office format conversions (each PDF should generate its own office file)
+    (parameters.fromExtension === 'pdf' && isOfficeFormat(parameters.toExtension)) ||
+    // Office files to PDF conversions (each file should be processed separately via LibreOffice)
+    (isOfficeFormat(parameters.fromExtension) && parameters.toExtension === 'pdf') ||
     // Web files to PDF conversions (each web file should generate its own PDF)
     ((isWebFormat(parameters.fromExtension) || parameters.fromExtension === 'web') &&
      parameters.toExtension === 'pdf') ||
@@ -98,7 +102,7 @@ export const createFileFromResponse = (
 export const convertProcessor = async (
   parameters: ConvertParameters,
   selectedFiles: File[]
-): Promise<File[]> => {
+): Promise<CustomProcessorResult> => {
   const processedFiles: File[] = [];
   const endpoint = getEndpointUrl(parameters.fromExtension, parameters.toExtension);
 
@@ -107,7 +111,9 @@ export const convertProcessor = async (
   }
 
   // Convert-specific routing logic: decide batch vs individual processing
-  if (shouldProcessFilesSeparately(selectedFiles, parameters)) {
+  const isSeparateProcessing = shouldProcessFilesSeparately(selectedFiles, parameters);
+
+  if (isSeparateProcessing) {
     // Individual processing for complex cases (PDF→image, smart detection, etc.)
     for (const file of selectedFiles) {
       try {
@@ -134,7 +140,14 @@ export const convertProcessor = async (
     processedFiles.push(convertedFile);
   }
 
-  return processedFiles;
+  // When batch processing multiple files into one output (e.g., 3 images → 1 PDF),
+  // mark all inputs as consumed even though there's only 1 output file
+  const isCombiningMultiple = !isSeparateProcessing && selectedFiles.length > 1;
+
+  return {
+    files: processedFiles,
+    consumedAllInputs: isCombiningMultiple,
+  };
 };
 
 // Static configuration object
@@ -151,7 +164,7 @@ export const useConvertOperation = () => {
   const customConvertProcessor = useCallback(async (
     parameters: ConvertParameters,
     selectedFiles: File[]
-  ): Promise<File[]> => {
+  ): Promise<CustomProcessorResult> => {
     return convertProcessor(parameters, selectedFiles);
   }, []);
 
diff --git a/frontend/src/core/hooks/tools/extractPages/useExtractPagesOperation.ts b/frontend/src/core/hooks/tools/extractPages/useExtractPagesOperation.ts
index 086fd65cc2..687dde1700 100644
--- a/frontend/src/core/hooks/tools/extractPages/useExtractPagesOperation.ts
+++ b/frontend/src/core/hooks/tools/extractPages/useExtractPagesOperation.ts
@@ -1,6 +1,6 @@
 import apiClient from '@app/services/apiClient';
 import { useTranslation } from 'react-i18next';
-import { ToolType, useToolOperation } from '@app/hooks/tools/shared/useToolOperation';
+import { ToolType, useToolOperation, CustomProcessorResult } from '@app/hooks/tools/shared/useToolOperation';
 import { createStandardErrorHandler } from '@app/utils/toolErrorHandler';
 import { ExtractPagesParameters, defaultParameters } from '@app/hooks/tools/extractPages/useExtractPagesParameters';
 import { pdfWorkerManager } from '@app/services/pdfWorkerManager';
@@ -23,7 +23,7 @@ async function resolveSelectionToCsv(expression: string, file: File): Promise<st
 export const extractPagesOperationConfig = {
   toolType: ToolType.custom,
   operationType: 'extractPages',
-  customProcessor: async (parameters: ExtractPagesParameters, files: File[]): Promise<File[]> => {
+  customProcessor: async (parameters: ExtractPagesParameters, files: File[]): Promise<CustomProcessorResult> => {
     const outputs: File[] = [];
 
     for (const file of files) {
@@ -43,7 +43,10 @@ export const extractPagesOperationConfig = {
       outputs.push(outFile);
     }
 
-    return outputs;
+    return {
+      files: outputs,
+      consumedAllInputs: false,
+    };
   },
   defaultParameters,
 } as const;
diff --git a/frontend/src/core/hooks/tools/removeAnnotations/useRemoveAnnotationsOperation.ts b/frontend/src/core/hooks/tools/removeAnnotations/useRemoveAnnotationsOperation.ts
index 4078b2b073..e4b176c8d6 100644
--- a/frontend/src/core/hooks/tools/removeAnnotations/useRemoveAnnotationsOperation.ts
+++ b/frontend/src/core/hooks/tools/removeAnnotations/useRemoveAnnotationsOperation.ts
@@ -1,10 +1,10 @@
 import { useTranslation } from 'react-i18next';
-import { useToolOperation, ToolType } from '@app/hooks/tools/shared/useToolOperation';
+import { useToolOperation, ToolType, CustomProcessorResult } from '@app/hooks/tools/shared/useToolOperation';
 import { createStandardErrorHandler } from '@app/utils/toolErrorHandler';
 import { RemoveAnnotationsParameters, defaultParameters } from '@app/hooks/tools/removeAnnotations/useRemoveAnnotationsParameters';
 import { PDFDocument, PDFName, PDFRef, PDFDict } from 'pdf-lib';
 // Client-side PDF processing using PDF-lib
-const removeAnnotationsProcessor = async (_parameters: RemoveAnnotationsParameters, files: File[]): Promise<File[]> => {
+const removeAnnotationsProcessor = async (_parameters: RemoveAnnotationsParameters, files: File[]): Promise<CustomProcessorResult> => {
   const processedFiles: File[] = [];
 
   for (const file of files) {
@@ -75,7 +75,10 @@ const removeAnnotationsProcessor = async (_parameters: RemoveAnnotationsParamete
     }
   }
 
-  return processedFiles;
+  return {
+    files: processedFiles,
+    consumedAllInputs: false,
+  };
 };
 
 // Static configuration object
diff --git a/frontend/src/core/hooks/tools/shared/useToolApiCalls.ts b/frontend/src/core/hooks/tools/shared/useToolApiCalls.ts
index a8e6a88a02..1ab8925f14 100644
--- a/frontend/src/core/hooks/tools/shared/useToolApiCalls.ts
+++ b/frontend/src/core/hooks/tools/shared/useToolApiCalls.ts
@@ -4,6 +4,7 @@ import apiClient from '@app/services/apiClient'; // Our configured instance
 import { processResponse, ResponseHandler } from '@app/utils/toolResponseProcessor';
 import { isEmptyOutput } from '@app/services/errorUtils';
 import type { ProcessingProgress } from '@app/hooks/tools/shared/useToolState';
+import type { StirlingFile, FileId } from '@app/types/fileContext';
 
 export interface ApiCallsConfig<TParams = void> {
   endpoint: string | ((params: TParams) => string);
@@ -18,14 +19,14 @@ export const useToolApiCalls = <TParams = void>() => {
 
   const processFiles = useCallback(async (
     params: TParams,
-    validFiles: File[],
+    validFiles: StirlingFile[],
     config: ApiCallsConfig<TParams>,
     onProgress: (progress: ProcessingProgress) => void,
     onStatus: (status: string) => void,
-    markFileError?: (fileId: string) => void,
-  ): Promise<{ outputFiles: File[]; successSourceIds: string[] }> => {
+    markFileError?: (fileId: FileId) => void,
+  ): Promise<{ outputFiles: File[]; successSourceIds: FileId[] }> => {
     const processedFiles: File[] = [];
-    const successSourceIds: string[] = [];
+    const successSourceIds: FileId[] = [];
     const failedFiles: string[] = [];
     const total = validFiles.length;
 
@@ -35,7 +36,7 @@ export const useToolApiCalls = <TParams = void>() => {
     for (let i = 0; i < validFiles.length; i++) {
       const file = validFiles[i];
 
-      console.debug('[processFiles] Start', { index: i, total, name: file.name, fileId: (file as any).fileId });
+      console.debug('[processFiles] Start', { index: i, total, name: file.name, fileId: file.fileId });
       onProgress({ current: i + 1, total, currentFileName: file.name });
       onStatus(`Processing ${file.name} (${i + 1}/${total})`);
 
@@ -47,7 +48,7 @@ export const useToolApiCalls = <TParams = void>() => {
           responseType: 'blob',
           cancelToken: cancelTokenRef.current?.token,
         });
-        console.debug('[processFiles] Response OK', { name: file.name, status: (response as any)?.status });
+        console.debug('[processFiles] Response OK', { name: file.name, status: response.status });
 
         // Forward to shared response processor (uses tool-specific responseHandler if provided)
         const responseFiles = await processResponse(
@@ -63,7 +64,7 @@ export const useToolApiCalls = <TParams = void>() => {
           console.warn('[processFiles] Empty output treated as failure', { name: file.name });
           failedFiles.push(file.name);
           try {
-            (markFileError as any)?.((file as any).fileId);
+            markFileError?.(file.fileId);
           } catch (e) {
             console.debug('markFileError', e);
           }
@@ -71,7 +72,7 @@ export const useToolApiCalls = <TParams = void>() => {
         }
         processedFiles.push(...responseFiles);
         // record source id as successful
-        successSourceIds.push((file as any).fileId);
+        successSourceIds.push(file.fileId);
         console.debug('[processFiles] Success', { name: file.name, produced: responseFiles.length });
 
       } catch (error) {
@@ -82,7 +83,7 @@ export const useToolApiCalls = <TParams = void>() => {
         failedFiles.push(file.name);
         // mark errored file so UI can highlight
         try {
-          (markFileError as any)?.((file as any).fileId);
+          markFileError?.(file.fileId);
         } catch (e) {
           console.debug('markFileError', e);
         }
diff --git a/frontend/src/core/hooks/tools/shared/useToolOperation.ts b/frontend/src/core/hooks/tools/shared/useToolOperation.ts
index e1dccd1e70..4804032d0d 100644
--- a/frontend/src/core/hooks/tools/shared/useToolOperation.ts
+++ b/frontend/src/core/hooks/tools/shared/useToolOperation.ts
@@ -8,6 +8,7 @@ import { useToolResources } from '@app/hooks/tools/shared/useToolResources';
 import { extractErrorMessage } from '@app/utils/toolErrorHandler';
 import { StirlingFile, extractFiles, FileId, StirlingFileStub, createStirlingFile } from '@app/types/fileContext';
 import { FILE_EVENTS } from '@app/services/errorUtils';
+import { getFilenameWithoutExtension } from '@app/utils/fileUtils';
 import { ResponseHandler } from '@app/utils/toolResponseProcessor';
 import { createChildStub, generateProcessedFileMetadata } from '@app/contexts/file/fileActions';
 import { ToolOperation } from '@app/types/file';
@@ -23,6 +24,20 @@ export enum ToolType {
   custom,
 }
 
+/**
+ * Result from custom processor with optional metadata about input consumption.
+ */
+export interface CustomProcessorResult {
+  /** Processed output files */
+  files: File[];
+  /**
+   * When true, marks all input files as successfully consumed regardless of output count.
+   * Use when operation combines N inputs into fewer outputs (e.g., 3 images → 1 PDF).
+   * When false/undefined, uses filename-based mapping to determine which inputs succeeded.
+   */
+  consumedAllInputs?: boolean;
+}
+
 /**
  * Configuration for tool operations defining processing behavior and API integration.
  *
@@ -98,8 +113,12 @@ export interface CustomToolOperationConfig<TParams> extends BaseToolOperationCon
    * Custom processing logic that completely bypasses standard file processing.
    * This tool handles all API calls, response processing, and file creation.
    * Use for tools with complex routing logic or non-standard processing requirements.
+   *
+   * Returns CustomProcessorResult with:
+   * - files: Processed output files
+   * - consumedAllInputs: true if operation combines N inputs → fewer outputs
    */
-  customProcessor: (params: TParams, files: File[]) => Promise<File[]>;
+  customProcessor: (params: TParams, files: File[]) => Promise<CustomProcessorResult>;
 }
 
 export type ToolOperationConfig<TParams = void> = SingleFileToolOperationConfig<TParams> | MultiFileToolOperationConfig<TParams> | CustomToolOperationConfig<TParams>;
@@ -172,17 +191,17 @@ export const useToolOperation = <TParams>(
     }
 
     // Handle zero-byte inputs explicitly: mark as error and continue with others
-    const zeroByteFiles = selectedFiles.filter(file => (file as any)?.size === 0);
+    const zeroByteFiles = selectedFiles.filter(file => file.size === 0);
     if (zeroByteFiles.length > 0) {
       try {
         for (const f of zeroByteFiles) {
-          (fileActions.markFileError as any)((f as any).fileId);
+          fileActions.markFileError(f.fileId);
         }
       } catch (e) {
         console.log('markFileError', e);
       }
     }
-    const validFiles = selectedFiles.filter(file => (file as any)?.size > 0);
+    const validFiles: StirlingFile[] = selectedFiles.filter(file => file.size > 0);
     if (validFiles.length === 0) {
       actions.setError(t('noValidFiles', 'No valid files to process'));
       return;
@@ -215,7 +234,7 @@ export const useToolOperation = <TParams>(
 
       try {
       let processedFiles: File[];
-        let successSourceIds: string[] = [];
+        let successSourceIds: FileId[] = [];
 
       // Use original files directly (no PDF metadata injection - history stored in IndexedDB)
       const filesForAPI = extractFiles(validFiles);
@@ -233,14 +252,14 @@ export const useToolOperation = <TParams>(
           console.debug('[useToolOperation] Multi-file start', { count: filesForAPI.length });
           const result = await processFiles(
             params,
-            filesForAPI,
+            validFiles,
             apiCallsConfig,
             actions.setProgress,
             actions.setStatus,
-            fileActions.markFileError as any
+            fileActions.markFileError
           );
           processedFiles = result.outputFiles;
-          successSourceIds = result.successSourceIds as any;
+          successSourceIds = result.successSourceIds;
           console.debug('[useToolOperation] Multi-file results', { outputFiles: processedFiles.length, successSources: result.successSourceIds.length });
           break;
         }
@@ -268,30 +287,40 @@ export const useToolOperation = <TParams>(
             processedFiles = await extractZipFiles(response.data);
           }
           // Assume all inputs succeeded together unless server provided an error earlier
-          successSourceIds = validFiles.map(f => (f as any).fileId) as any;
+          successSourceIds = validFiles.map(f => f.fileId);
           break;
         }
 
         case ToolType.custom: {
           actions.setStatus('Processing files...');
-          processedFiles = await config.customProcessor(params, filesForAPI);
-          // Try to map outputs back to inputs by filename (before extension)
-          const inputBaseNames = new Map<string, string>();
-          for (const f of validFiles) {
-            const base = (f.name || '').replace(/\.[^.]+$/, '').toLowerCase();
-            inputBaseNames.set(base, (f as any).fileId);
-          }
-          const mappedSuccess: string[] = [];
-          for (const out of processedFiles) {
-            const base = (out.name || '').replace(/\.[^.]+$/, '').toLowerCase();
-            const id = inputBaseNames.get(base);
-            if (id) mappedSuccess.push(id);
-          }
-          // Fallback to naive alignment if names don't match
-          if (mappedSuccess.length === 0) {
-            successSourceIds = validFiles.slice(0, processedFiles.length).map(f => (f as any).fileId) as any;
+          const result = await config.customProcessor(params, filesForAPI);
+
+          processedFiles = result.files;
+          const consumedAllInputs = result.consumedAllInputs || false;
+
+          // If consumedAllInputs flag is set, mark all inputs as successful
+          // (used for operations that combine N inputs into fewer outputs)
+          if (consumedAllInputs) {
+            successSourceIds = validFiles.map(f => f.fileId);
           } else {
-            successSourceIds = mappedSuccess as any;
+            // Try to map outputs back to inputs by filename (before extension)
+            const inputBaseNames = new Map<string, FileId>();
+            for (const f of validFiles) {
+              const base = getFilenameWithoutExtension(f.name || '');
+              inputBaseNames.set(base, f.fileId);
+            }
+            const mappedSuccess: FileId[] = [];
+            for (const out of processedFiles) {
+              const base = getFilenameWithoutExtension(out.name || '');
+              const id = inputBaseNames.get(base);
+              if (id) mappedSuccess.push(id);
+            }
+            // Fallback to naive alignment if names don't match
+            if (mappedSuccess.length === 0) {
+              successSourceIds = validFiles.slice(0, processedFiles.length).map(f => f.fileId);
+            } else {
+              successSourceIds = mappedSuccess;
+            }
           }
           break;
         }
@@ -299,16 +328,16 @@ export const useToolOperation = <TParams>(
 
       // Normalize error flags across tool types: mark failures, clear successes
       try {
-        const allInputIds = validFiles.map(f => (f as any).fileId) as unknown as string[];
-        const okSet = new Set((successSourceIds as unknown as string[]) || []);
+        const allInputIds = validFiles.map(f => f.fileId);
+        const okSet = new Set(successSourceIds);
         // Clear errors on successes
         for (const okId of okSet) {
-          try { (fileActions.clearFileError as any)(okId); } catch (_e) { void _e; }
+          try { fileActions.clearFileError(okId); } catch (_e) { void _e; }
         }
         // Mark errors on inputs that didn't succeed
         for (const id of allInputIds) {
           if (!okSet.has(id)) {
-            try { (fileActions.markFileError as any)(id); } catch (_e) { void _e; }
+            try { fileActions.markFileError(id); } catch (_e) { void _e; }
           }
         }
       } catch (_e) { void _e; }
@@ -316,12 +345,12 @@ export const useToolOperation = <TParams>(
       if (externalErrorFileIds.length > 0) {
         // If backend told us which sources failed, prefer that mapping
         successSourceIds = validFiles
-          .map(f => (f as any).fileId)
-          .filter(id => !externalErrorFileIds.includes(id)) as any;
+          .map(f => f.fileId)
+          .filter(id => !externalErrorFileIds.includes(id));
         // Also mark failed IDs immediately
         try {
           for (const badId of externalErrorFileIds) {
-            (fileActions.markFileError as any)(badId);
+            fileActions.markFileError(badId as FileId);
           }
         } catch (_e) { void _e; }
       }
@@ -370,7 +399,7 @@ export const useToolOperation = <TParams>(
         );
         // Always create child stubs linking back to the successful source inputs
         const successInputStubs = successSourceIds
-          .map((id) => selectors.getStirlingFileStub(id as any))
+          .map((id) => selectors.getStirlingFileStub(id))
           .filter(Boolean) as StirlingFileStub[];
 
         if (successInputStubs.length !== processedFiles.length) {
@@ -396,7 +425,7 @@ export const useToolOperation = <TParams>(
           return createStirlingFile(file, childStub.id);
         });
         // Build consumption arrays aligned to the successful source IDs
-        const toConsumeInputIds = successSourceIds.filter((id: string) => inputFileIds.includes(id as any)) as unknown as FileId[];
+        const toConsumeInputIds = successSourceIds.filter((id) => inputFileIds.includes(id));
         // Outputs and stubs are already ordered by success sequence
         console.debug('[useToolOperation] Consuming files', { inputCount: inputFileIds.length, toConsume: toConsumeInputIds.length });
         const outputFileIds = await consumeFiles(toConsumeInputIds, outputStirlingFiles, outputStirlingFileStubs);
@@ -413,25 +442,27 @@ export const useToolOperation = <TParams>(
     } catch (error: any) {
       // Centralized 422 handler: mark provided IDs in errorFileIds
       try {
-        const status = (error?.response?.status as number | undefined);
-        if (status === 422) {
+        const status = error?.response?.status;
+        if (typeof status === 'number' && status === 422) {
           const payload = error?.response?.data;
-          let parsed: any = payload;
+          let parsed: unknown = payload;
           if (typeof payload === 'string') {
             try { parsed = JSON.parse(payload); } catch { parsed = payload; }
-          } else if (payload && typeof (payload as any).text === 'function') {
+          } else if (payload && typeof (payload as Blob).text === 'function') {
             // Blob or Response-like object from axios when responseType='blob'
             const text = await (payload as Blob).text();
             try { parsed = JSON.parse(text); } catch { parsed = text; }
           }
-          let ids: string[] | undefined = Array.isArray(parsed?.errorFileIds) ? parsed.errorFileIds : undefined;
+          let ids: string[] | undefined = Array.isArray((parsed as { errorFileIds?: unknown })?.errorFileIds)
+            ? (parsed as { errorFileIds: string[] }).errorFileIds
+            : undefined;
           if (!ids && typeof parsed === 'string') {
             const match = parsed.match(/[0-9a-fA-F]{8}-[0-9a-fA-F]{4}-[0-9a-fA-F]{4}-[0-9a-fA-F]{4}-[0-9a-fA-F]{12}/g);
             if (match && match.length > 0) ids = Array.from(new Set(match));
           }
           if (ids && ids.length > 0) {
             for (const badId of ids) {
-              try { (fileActions.markFileError as any)(badId); } catch (_e) { void _e; }
+              try { fileActions.markFileError(badId as FileId); } catch (_e) { void _e; }
             }
             actions.setStatus('Process failed due to invalid/corrupted file(s)');
             // Avoid duplicating toast messaging here
diff --git a/frontend/src/core/utils/automationExecutor.ts b/frontend/src/core/utils/automationExecutor.ts
index 6f1234f810..2651784e18 100644
--- a/frontend/src/core/utils/automationExecutor.ts
+++ b/frontend/src/core/utils/automationExecutor.ts
@@ -158,8 +158,8 @@ export const executeToolOperationWithPrefix = async (
   try {
     // Check if tool uses custom processor (like Convert tool)
     if (config.customProcessor) {
-      const resultFiles = await config.customProcessor(parameters, files);
-      return resultFiles;
+      const result = await config.customProcessor(parameters, files);
+      return result.files;
     }
 
     // Execute based on tool type
diff --git a/frontend/src/core/utils/convertUtils.ts b/frontend/src/core/utils/convertUtils.ts
index ef2836058f..b1e87161ba 100644
--- a/frontend/src/core/utils/convertUtils.ts
+++ b/frontend/src/core/utils/convertUtils.ts
@@ -60,6 +60,18 @@ export const isWebFormat = (extension: string): boolean => {
   return ['html', 'zip'].includes(extension.toLowerCase());
 };
 
+/**
+ * Checks if the given extension is an office format (Word, Excel, PowerPoint, OpenOffice)
+ * These formats use LibreOffice for conversion and require individual file processing
+ */
+export const isOfficeFormat = (extension: string): boolean => {
+  return [
+    'docx', 'doc', 'odt',  // Word processors
+    'xlsx', 'xls', 'ods',  // Spreadsheets
+    'pptx', 'ppt', 'odp'   // Presentations
+  ].includes(extension.toLowerCase());
+};
+
 /**
  * Gets available target extensions for a given source extension
  * Extracted from useConvertParameters to be reusable in automation settings
diff --git a/frontend/src/core/utils/fileUtils.ts b/frontend/src/core/utils/fileUtils.ts
index 0f14714019..4061884b55 100644
--- a/frontend/src/core/utils/fileUtils.ts
+++ b/frontend/src/core/utils/fileUtils.ts
@@ -52,6 +52,29 @@ export function detectFileExtension(filename: string): string {
   return extension;
 }
 
+/**
+ * Removes the file extension from a filename
+ * @param filename - The filename to process
+ * @param options - Options for processing
+ * @param options.preserveCase - If true, preserves original case. If false (default), converts to lowercase
+ * @returns Filename without extension
+ * @example
+ * getFilenameWithoutExtension('document.pdf') // 'document'
+ * getFilenameWithoutExtension('my.file.name.txt') // 'my.file.name'
+ * getFilenameWithoutExtension('REPORT.PDF', { preserveCase: true }) // 'REPORT'
+ */
+export function getFilenameWithoutExtension(
+  filename: string,
+  options: { preserveCase?: boolean } = {}
+): string {
+  if (!filename || typeof filename !== 'string') return '';
+
+  const { preserveCase = false } = options;
+  const withoutExtension = filename.replace(/\.[^.]+$/, '');
+
+  return preserveCase ? withoutExtension : withoutExtension.toLowerCase();
+}
+
 /**
  * Checks if a file is a PDF based on extension and MIME type
  * @param file - File or file-like object with name and type properties