diff --git a/apps/red-ui/src/app/app.module.ts b/apps/red-ui/src/app/app.module.ts
index b07e4ce16..5a8d2ae4e 100644
--- a/apps/red-ui/src/app/app.module.ts
+++ b/apps/red-ui/src/app/app.module.ts
@@ -104,6 +104,7 @@ import { RuleSetActionsComponent } from './components/rule-set-actions/rule-set-
 import { RuleSetViewSwitchComponent } from './components/rule-set-view-switch/rule-set-view-switch.component';
 import { MatSliderModule } from '@angular/material/slider';
 import { PendingChangesGuard } from './utils/can-deactivate.guard';
+import { OverwriteFilesDialogComponent } from './dialogs/overwrite-files-dialog/overwrite-files-dialog.component';
 
 export function HttpLoaderFactory(httpClient: HttpClient) {
     return new TranslateHttpLoader(httpClient, '/assets/i18n/', '.json');
@@ -276,6 +277,7 @@ const matImports = [
         ProjectOverviewScreenComponent,
         AddEditProjectDialogComponent,
         ConfirmationDialogComponent,
+        OverwriteFilesDialogComponent,
         FilePreviewScreenComponent,
         PdfViewerComponent,
         AssignOwnerDialogComponent,
diff --git a/apps/red-ui/src/app/dialogs/dialog.service.ts b/apps/red-ui/src/app/dialogs/dialog.service.ts
index 6c39092b4..edf13c942 100644
--- a/apps/red-ui/src/app/dialogs/dialog.service.ts
+++ b/apps/red-ui/src/app/dialogs/dialog.service.ts
@@ -22,6 +22,7 @@ import { ManualAnnotationService } from '../screens/file/service/manual-annotati
 import { ProjectWrapper } from '../state/model/project.wrapper';
 import { AddEditDictionaryDialogComponent } from '../screens/admin/dictionary-listing-screen/add-edit-dictionary-dialog/add-edit-dictionary-dialog.component';
 import { AddEditRuleSetDialogComponent } from '../screens/admin/rule-sets-listing-screen/add-edit-rule-set-dialog/add-edit-rule-set-dialog.component';
+import { OverwriteFilesDialogComponent } from './overwrite-files-dialog/overwrite-files-dialog.component';
 
 const dialogConfig = {
     width: '662px',
@@ -331,4 +332,18 @@ export class DialogService {
 
         return ref;
     }
+
+    openOverwriteFileDialog(filename: string): Promise<{ option?: 'overwrite' | 'no-overwrite'; remember?: boolean; cancel?: boolean }> {
+        const ref = this._dialog.open(OverwriteFilesDialogComponent, {
+            ...dialogConfig,
+            data: filename
+        });
+
+        return ref
+            .afterClosed()
+            .toPromise()
+            .then((res) => {
+                return res || { cancel: true };
+            });
+    }
 }
diff --git a/apps/red-ui/src/app/dialogs/overwrite-files-dialog/overwrite-files-dialog.component.html b/apps/red-ui/src/app/dialogs/overwrite-files-dialog/overwrite-files-dialog.component.html
new file mode 100644
index 000000000..962a5daa9
--- /dev/null
+++ b/apps/red-ui/src/app/dialogs/overwrite-files-dialog/overwrite-files-dialog.component.html
@@ -0,0 +1,17 @@
+<section class="dialog">
+    <div class="dialog-header heading-l" translate="overwrite-files-dialog.title"></div>
+
+    <div class="dialog-content">
+        <p [innerHTML]="'overwrite-files-dialog.question' | translate: { filename: filename }"></p>
+
+        <mat-checkbox [checked]="remember" (change)="remember = !remember" color="primary">
+            {{ 'overwrite-files-dialog.options.remember' | translate }}
+        </mat-checkbox>
+    </div>
+
+    <div class="dialog-actions">
+        <div class="all-caps-label primary pointer" (click)="selectOption('overwrite')" translate="overwrite-files-dialog.options.overwrite"></div>
+        <div class="all-caps-label primary pointer" (click)="selectOption('no-overwrite')" translate="overwrite-files-dialog.options.no-overwrite"></div>
+        <div class="all-caps-label cancel" (click)="cancel()" translate="overwrite-files-dialog.options.cancel"></div>
+    </div>
+</section>
diff --git a/apps/red-ui/src/app/dialogs/overwrite-files-dialog/overwrite-files-dialog.component.scss b/apps/red-ui/src/app/dialogs/overwrite-files-dialog/overwrite-files-dialog.component.scss
new file mode 100644
index 000000000..d2bca127f
--- /dev/null
+++ b/apps/red-ui/src/app/dialogs/overwrite-files-dialog/overwrite-files-dialog.component.scss
@@ -0,0 +1,7 @@
+mat-checkbox {
+    margin-top: 16px;
+}
+
+.dialog-actions > div:not(:last-child) {
+    margin-right: 32px;
+}
diff --git a/apps/red-ui/src/app/dialogs/overwrite-files-dialog/overwrite-files-dialog.component.ts b/apps/red-ui/src/app/dialogs/overwrite-files-dialog/overwrite-files-dialog.component.ts
new file mode 100644
index 000000000..0f0d93a51
--- /dev/null
+++ b/apps/red-ui/src/app/dialogs/overwrite-files-dialog/overwrite-files-dialog.component.ts
@@ -0,0 +1,28 @@
+import { Component, Inject, OnInit } from '@angular/core';
+import { TranslateService } from '@ngx-translate/core';
+import { MAT_DIALOG_DATA, MatDialogRef } from '@angular/material/dialog';
+
+@Component({
+    selector: 'redaction-overwrite-files-dialog',
+    templateUrl: './overwrite-files-dialog.component.html',
+    styleUrls: ['./overwrite-files-dialog.component.scss']
+})
+export class OverwriteFilesDialogComponent implements OnInit {
+    public remember = false;
+
+    constructor(
+        private readonly _translateService: TranslateService,
+        public dialogRef: MatDialogRef<OverwriteFilesDialogComponent>,
+        @Inject(MAT_DIALOG_DATA) public filename: string
+    ) {}
+
+    ngOnInit(): void {}
+
+    cancel() {
+        this.dialogRef.close();
+    }
+
+    selectOption(option: 'overwrite' | 'no-overwrite') {
+        this.dialogRef.close({ option, remember: this.remember });
+    }
+}
diff --git a/apps/red-ui/src/app/screens/project-overview-screen/project-overview-screen.component.ts b/apps/red-ui/src/app/screens/project-overview-screen/project-overview-screen.component.ts
index 1df08a03c..bf8d37810 100644
--- a/apps/red-ui/src/app/screens/project-overview-screen/project-overview-screen.component.ts
+++ b/apps/red-ui/src/app/screens/project-overview-screen/project-overview-screen.component.ts
@@ -212,13 +212,15 @@ export class ProjectOverviewScreenComponent implements OnInit, OnDestroy {
         event.preventDefault();
     }
 
-    uploadFiles(files: File[] | FileList) {
-        this._uploadFiles(convertFiles(files, this.appStateService.activeProjectId));
+    async uploadFiles(files: File[] | FileList) {
+        await this._uploadFiles(convertFiles(files, this.appStateService.activeProjectId));
     }
 
-    private _uploadFiles(files: FileUploadModel[]) {
-        this._fileUploadService.uploadFiles(files);
-        this._uploadStatusOverlayService.openStatusOverlay();
+    private async _uploadFiles(files: FileUploadModel[]) {
+        const fileCount = await this._fileUploadService.uploadFiles(files);
+        if (fileCount) {
+            this._uploadStatusOverlayService.openStatusOverlay();
+        }
         this._changeDetectorRef.detectChanges();
     }
 
diff --git a/apps/red-ui/src/app/upload/file-drop/file-drop.component.ts b/apps/red-ui/src/app/upload/file-drop/file-drop.component.ts
index 193f8558a..663dbe54b 100644
--- a/apps/red-ui/src/app/upload/file-drop/file-drop.component.ts
+++ b/apps/red-ui/src/app/upload/file-drop/file-drop.component.ts
@@ -44,9 +44,11 @@ export class FileDropComponent implements OnInit {
         event.preventDefault();
     }
 
-    uploadFiles(files: FileUploadModel[]) {
-        this._fileUploadService.uploadFiles(files);
-        this._uploadStatusOverlayService.openStatusOverlay();
+    async uploadFiles(files: FileUploadModel[]) {
+        const fileCount = await this._fileUploadService.uploadFiles(files);
+        if (fileCount) {
+            this._uploadStatusOverlayService.openStatusOverlay();
+        }
         this._dialogRef.detach();
         this._changeDetectorRef.detectChanges();
     }
diff --git a/apps/red-ui/src/app/upload/file-upload.service.ts b/apps/red-ui/src/app/upload/file-upload.service.ts
index d02960f80..dbd377a24 100644
--- a/apps/red-ui/src/app/upload/file-upload.service.ts
+++ b/apps/red-ui/src/app/upload/file-upload.service.ts
@@ -6,6 +6,7 @@ import { FileManagementControllerService } from '@redaction/red-ui-http';
 import { interval, Subscription } from 'rxjs';
 import { AppConfigKey, AppConfigService } from '../app-config/app-config.service';
 import { TranslateService } from '@ngx-translate/core';
+import { DialogService } from '../dialogs/dialog.service';
 
 @Injectable({
     providedIn: 'root'
@@ -23,7 +24,8 @@ export class FileUploadService {
         private readonly _applicationRef: ApplicationRef,
         private readonly _translateService: TranslateService,
         private readonly _appConfigService: AppConfigService,
-        private readonly _fileManagementControllerService: FileManagementControllerService
+        private readonly _fileManagementControllerService: FileManagementControllerService,
+        private readonly _dialogService: DialogService
     ) {
         interval(2500).subscribe((val) => {
             this._handleUploads();
@@ -39,20 +41,41 @@ export class FileUploadService {
         }
     }
 
-    uploadFiles(files: FileUploadModel[]) {
+    async uploadFiles(files: FileUploadModel[]): Promise<number> {
         const maxSizeMB = this._appConfigService.getConfig(AppConfigKey.MAX_FILE_SIZE_MB, 50);
         const maxSizeBytes = maxSizeMB * 1024 * 1024;
-        files.forEach((file) => {
+        const projectFiles = this._appStateService.activeProject.files;
+        let option: 'overwrite' | 'no-overwrite' | undefined = undefined;
+        for (let idx = 0; idx < files.length; ++idx) {
+            const file = files[idx];
+            let currentOption = option;
+            if (!!projectFiles.find((pf) => pf.filename === file.file.name)) {
+                if (!option) {
+                    const res = await this._dialogService.openOverwriteFileDialog(file.file.name);
+                    if (res.cancel) {
+                        return;
+                    }
+                    currentOption = res.option;
+                    option = res.remember ? currentOption : undefined;
+                }
+
+                if (currentOption === 'no-overwrite') {
+                    files.splice(idx, 1);
+                    --idx;
+                    continue;
+                }
+            }
             if (file.size > maxSizeBytes) {
                 file.completed = true;
                 file.error = { message: this._translateService.instant('upload-status.error.file-size', { size: maxSizeMB }) };
                 file.sizeError = true;
             }
-        });
+        }
         this.files.push(...files);
         files.forEach((newFile) => {
             this.scheduleUpload(newFile);
         });
+        return files.length;
     }
 
     stopAllUploads() {
diff --git a/apps/red-ui/src/assets/i18n/en.json b/apps/red-ui/src/assets/i18n/en.json
index 79b16d29f..d546729e5 100644
--- a/apps/red-ui/src/assets/i18n/en.json
+++ b/apps/red-ui/src/assets/i18n/en.json
@@ -695,5 +695,15 @@
     "rule-editor": "Rule Editor",
     "watermark": "Watermark",
     "pending-changes-guard": "WARNING: You have unsaved changes. Press Cancel to go back and save these changes, or OK to lose these changes.",
-    "reset-filters": "Reset Filters"
+    "reset-filters": "Reset Filters",
+    "overwrite-files-dialog": {
+        "title": "File already exists!",
+        "question": "<b>{{filename}}</b> already exists. What do you want to do?",
+        "options": {
+            "overwrite": "Overwrite",
+            "no-overwrite": "Keep old file",
+            "cancel": "Cancel all uploads",
+            "remember": "Remember option"
+        }
+    }
 }