diff --git a/apps/red-ui/src/app/screens/file/file-preview-screen/file-preview-screen.component.html b/apps/red-ui/src/app/screens/file/file-preview-screen/file-preview-screen.component.html
index 48afed6cd..d6f91925f 100644
--- a/apps/red-ui/src/app/screens/file/file-preview-screen/file-preview-screen.component.html
+++ b/apps/red-ui/src/app/screens/file/file-preview-screen/file-preview-screen.component.html
@@ -50,7 +50,7 @@
                         : 'report.unavailable-single'
                     ) | translate
                 "
-                [matTooltipPosition]="'above'"
+                matTooltipPosition="above"
             >
                 <button
                     mat-icon-button
@@ -67,8 +67,16 @@
             </button>
             <button
                 (click)="reanalyseFile($event)"
+                [class.warn]="appStateService.fileNotUpToDateWithDictionary()"
                 *ngIf="appStateService.canReanalyseFile()"
                 mat-icon-button
+                #reanalyseTooltip="matTooltip"
+                [matTooltip]="
+                    appStateService.fileNotUpToDateWithDictionary()
+                        ? ('file-preview.reanalyse-notification' | translate)
+                        : null
+                "
+                matTooltipClass="warn"
             >
                 <mat-icon svgIcon="red:refresh"></mat-icon>
             </button>
@@ -83,7 +91,7 @@
                         : 'project-overview.under-approval'
                     ) | translate
                 "
-                [matTooltipPosition]="'above'"
+                matTooltipPosition="above"
             >
                 <mat-icon svgIcon="red:check-alt"></mat-icon>
             </button>
@@ -98,7 +106,7 @@
                         : 'project-overview.under-review'
                     ) | translate
                 "
-                [matTooltipPosition]="'above'"
+                matTooltipPosition="above"
                 color="accent"
                 mat-icon-button
             >
diff --git a/apps/red-ui/src/app/screens/file/file-preview-screen/file-preview-screen.component.ts b/apps/red-ui/src/app/screens/file/file-preview-screen/file-preview-screen.component.ts
index d6f9cd197..bcb6dde60 100644
--- a/apps/red-ui/src/app/screens/file/file-preview-screen/file-preview-screen.component.ts
+++ b/apps/red-ui/src/app/screens/file/file-preview-screen/file-preview-screen.component.ts
@@ -8,11 +8,7 @@ import {
     ViewChild
 } from '@angular/core';
 import { ActivatedRoute, Router } from '@angular/router';
-import {
-    ReanalysisControllerService,
-    ViewedPages,
-    ViewedPagesControllerService
-} from '@redaction/red-ui-http';
+import { ReanalysisControllerService } from '@redaction/red-ui-http';
 import { AppStateService } from '../../../state/app-state.service';
 import { WebViewerInstance } from '@pdftron/webviewer';
 import { PdfViewerComponent } from '../pdf-viewer/pdf-viewer.component';
@@ -34,9 +30,10 @@ import { AnnotationDrawService } from '../service/annotation-draw.service';
 import { AnnotationProcessingService } from '../service/annotation-processing.service';
 import { FilterModel } from '../../../common/filter/model/filter.model';
 import { tap } from 'rxjs/operators';
-import { NotificationService, NotificationType } from '../../../notification/notification.service';
+import { NotificationService } from '../../../notification/notification.service';
 import { TranslateService } from '@ngx-translate/core';
 import { FileStatusWrapper } from '../model/file-status.wrapper';
+import { MatTooltip } from '@angular/material/tooltip';
 
 const KEY_ARRAY = ['ArrowLeft', 'ArrowRight', 'ArrowUp', 'ArrowDown'];
 
@@ -46,6 +43,30 @@ const KEY_ARRAY = ['ArrowLeft', 'ArrowRight', 'ArrowUp', 'ArrowDown'];
     styleUrls: ['./file-preview-screen.component.scss']
 })
 export class FilePreviewScreenComponent implements OnInit {
+    private projectId: string;
+    private _activeViewer: 'ANNOTATED' | 'REDACTED' = 'ANNOTATED';
+    private instance: WebViewerInstance;
+    private _dialogRef: MatDialogRef<any>;
+
+    @ViewChild(PdfViewerComponent) private _viewerComponent: PdfViewerComponent;
+    @ViewChild('annotationsElement') private _annotationsElement: ElementRef;
+    @ViewChild('quickNavigation') private _quickNavigationElement: ElementRef;
+    @ViewChild('reanalyseTooltip') private _reanalyseTooltip: MatTooltip;
+
+    public fileData: FileDataModel;
+    public fileId: string;
+    public annotations: AnnotationWrapper[] = [];
+    public displayedAnnotations: { [key: number]: { annotations: AnnotationWrapper[] } } = {};
+    public selectedAnnotation: AnnotationWrapper;
+    public pagesPanelActive = true;
+    public viewReady = false;
+    public filters: FilterModel[];
+
+    private _activeMenuAnnotation: AnnotationWrapper;
+    loadingMessage: string;
+
+    canPerformAnnotationActions: boolean;
+
     constructor(
         public readonly appStateService: AppStateService,
         public readonly userService: UserService,
@@ -61,7 +82,6 @@ export class FilePreviewScreenComponent implements OnInit {
         private readonly _manualAnnotationService: ManualAnnotationService,
         private readonly _fileDownloadService: FileDownloadService,
         private readonly _reanalysisControllerService: ReanalysisControllerService,
-
         private ngZone: NgZone
     ) {
         this._activatedRoute.params.subscribe((params) => {
@@ -95,29 +115,6 @@ export class FilePreviewScreenComponent implements OnInit {
         return this.instance?.docViewer?.getCurrentPage();
     }
 
-    private projectId: string;
-    private _activeViewer: 'ANNOTATED' | 'REDACTED' = 'ANNOTATED';
-    private instance: WebViewerInstance;
-    private _dialogRef: MatDialogRef<any>;
-
-    @ViewChild(PdfViewerComponent) private _viewerComponent: PdfViewerComponent;
-    @ViewChild('annotationsElement') private _annotationsElement: ElementRef;
-    @ViewChild('quickNavigation') private _quickNavigationElement: ElementRef;
-
-    public fileData: FileDataModel;
-    public fileId: string;
-    public annotations: AnnotationWrapper[] = [];
-    public displayedAnnotations: { [key: number]: { annotations: AnnotationWrapper[] } } = {};
-    public selectedAnnotation: AnnotationWrapper;
-    public pagesPanelActive = true;
-    public viewReady = false;
-    public filters: FilterModel[];
-
-    private _activeMenuAnnotation: AnnotationWrapper;
-    loadingMessage: string;
-
-    canPerformAnnotationActions: boolean;
-
     get canNotSwitchToRedactedView() {
         return (
             this.appStateService.fileNotUpToDateWithDictionary() ||
@@ -488,7 +485,7 @@ export class FilePreviewScreenComponent implements OnInit {
     viewerReady($event: WebViewerInstance) {
         this.instance = $event;
         this.viewReady = true;
-        this._displayNewRuleToast();
+        this._reanalyseTooltip.show();
         this._cleanupAndRedrawManualAnnotations();
     }
 
@@ -561,31 +558,4 @@ export class FilePreviewScreenComponent implements OnInit {
         $event.stopPropagation();
         this._fileActionService.undoApproveOrUnderApproval().subscribe(() => {});
     }
-
-    private _displayNewRuleToast() {
-        if (this.appStateService.fileNotUpToDateWithDictionary()) {
-            this._notificationService.showToastNotification(
-                `${this._translateService.instant('project-overview.new-rule.toast.message-file')}`,
-                null,
-                NotificationType.WARNING,
-                {
-                    disableTimeOut: true,
-                    positionClass: 'toast-top-left',
-                    actions: [
-                        {
-                            title: this._translateService.instant(
-                                'project-overview.new-rule.toast.actions.reanalyse-file'
-                            ),
-                            action: () => this.reanalyseFile()
-                        },
-                        {
-                            title: this._translateService.instant(
-                                'project-overview.new-rule.toast.actions.later'
-                            )
-                        }
-                    ]
-                }
-            );
-        }
-    }
 }
diff --git a/apps/red-ui/src/app/screens/project-listing-screen/project-listing-screen.component.html b/apps/red-ui/src/app/screens/project-listing-screen/project-listing-screen.component.html
index a1faf643e..3cac4f300 100644
--- a/apps/red-ui/src/app/screens/project-listing-screen/project-listing-screen.component.html
+++ b/apps/red-ui/src/app/screens/project-listing-screen/project-listing-screen.component.html
@@ -166,7 +166,7 @@
                             <button
                                 (click)="openDeleteProjectDialog($event, pw.project)"
                                 [matTooltip]="'project-listing.delete.action' | translate"
-                                [matTooltipPosition]="'above'"
+                                matTooltipPosition="above"
                                 *ngIf="userService.isManager(user)"
                                 color="accent"
                                 mat-icon-button
@@ -177,7 +177,7 @@
                             <button
                                 (click)="openEditProjectDialog($event, pw.project)"
                                 [matTooltip]="'project-listing.edit.action' | translate"
-                                [matTooltipPosition]="'above'"
+                                matTooltipPosition="above"
                                 *ngIf="userService.isManager(user)"
                                 color="accent"
                                 mat-icon-button
@@ -190,7 +190,7 @@
                                     (pw.allFilesApproved ? 'report.action' : 'report.unavailable')
                                         | translate
                                 "
-                                [matTooltipPosition]="'above'"
+                                matTooltipPosition="above"
                                 *ngIf="appStateService.isManagerAndOwner(pw.project) && pw.hasFiles"
                             >
                                 <button
@@ -205,7 +205,7 @@
                             <button
                                 (click)="openAssignProjectOwnerDialog($event, pw.project)"
                                 [matTooltip]="'project-listing.assign.action' | translate"
-                                [matTooltipPosition]="'above'"
+                                matTooltipPosition="above"
                                 *ngIf="userService.isManager(user)"
                                 color="accent"
                                 mat-icon-button
@@ -218,7 +218,7 @@
                                 (click)="reanalyseProject($event, pw.project)"
                                 mat-icon-button
                                 [matTooltip]="'project-listing.reanalyse.action' | translate"
-                                [matTooltipPosition]="'above'"
+                                matTooltipPosition="above"
                             >
                                 <mat-icon svgIcon="red:refresh"></mat-icon>
                             </button>
diff --git a/apps/red-ui/src/app/screens/project-overview-screen/project-details/project-details.component.html b/apps/red-ui/src/app/screens/project-overview-screen/project-details/project-details.component.html
index 1dadeee90..3402ba452 100644
--- a/apps/red-ui/src/app/screens/project-overview-screen/project-details/project-details.component.html
+++ b/apps/red-ui/src/app/screens/project-overview-screen/project-details/project-details.component.html
@@ -17,7 +17,7 @@
             ) | translate
         "
         *ngIf="appStateService.isActiveProjectOwnerAndManager"
-        [matTooltipPosition]="'above'"
+        matTooltipPosition="above"
     >
         <button
             (click)="downloadRedactionReport($event)"
diff --git a/apps/red-ui/src/app/screens/project-overview-screen/project-overview-screen.component.html b/apps/red-ui/src/app/screens/project-overview-screen/project-overview-screen.component.html
index aea8acd60..d4fbdbce5 100644
--- a/apps/red-ui/src/app/screens/project-overview-screen/project-overview-screen.component.html
+++ b/apps/red-ui/src/app/screens/project-overview-screen/project-overview-screen.component.html
@@ -159,21 +159,24 @@
                         ></div>
                     </div>
 
-                    <div>
-                        <div
-                            [class.disabled]="isPending(fileStatus) || isProcessing(fileStatus)"
-                            [class.error]="isError(fileStatus)"
-                            class="table-item-title"
-                            [matTooltipPosition]="'above'"
-                            [matTooltip]="'[' + fileStatus.status + '] ' + fileStatus.filename"
-                        >
-                            {{ fileStatus.filename }}
+                    <div
+                        matTooltipPosition="above"
+                        [matTooltip]="'[' + fileStatus.status + '] ' + fileStatus.filename"
+                    >
+                        <div class="filename-wrapper">
+                            <div
+                                [class.disabled]="isPending(fileStatus) || isProcessing(fileStatus)"
+                                [class.error]="isError(fileStatus)"
+                                class="table-item-title"
+                            >
+                                {{ fileStatus.filename }}
+                            </div>
+                            <span
+                                *ngIf="appStateService.fileNotUpToDateWithDictionary(fileStatus)"
+                                class="pill"
+                                translate="project-overview.new-rule.label"
+                            ></span>
                         </div>
-                        <span
-                            *ngIf="appStateService.fileNotUpToDateWithDictionary(fileStatus)"
-                            class="pill"
-                            translate="project-overview.new-rule.label"
-                        ></span>
                     </div>
 
                     <div>
@@ -239,7 +242,7 @@
                                     fileStatus.isError
                                 "
                                 [matTooltip]="'project-overview.delete.action' | translate"
-                                [matTooltipPosition]="'above'"
+                                matTooltipPosition="above"
                                 color="accent"
                                 mat-icon-button
                             >
@@ -257,7 +260,7 @@
                                     appStateService.isActiveProjectOwnerAndManager &&
                                     !isError(fileStatus)
                                 "
-                                [matTooltipPosition]="'above'"
+                                matTooltipPosition="above"
                             >
                                 <button
                                     (click)="downloadFileRedactionReport($event, fileStatus)"
@@ -276,7 +279,7 @@
                                     !fileStatus.isApprovedOrUnderApproval
                                 "
                                 [matTooltip]="'project-overview.assign.action' | translate"
-                                [matTooltipPosition]="'above'"
+                                matTooltipPosition="above"
                                 color="accent"
                                 mat-icon-button
                             >
@@ -286,7 +289,7 @@
                                 (click)="reanalyseFile($event, fileStatus)"
                                 *ngIf="appStateService.canReanalyseFile(fileStatus)"
                                 [matTooltip]="'project-overview.reanalyse.action' | translate"
-                                [matTooltipPosition]="'above'"
+                                matTooltipPosition="above"
                                 color="accent"
                                 mat-icon-button
                             >
@@ -304,7 +307,7 @@
                                         : 'project-overview.under-approval'
                                     ) | translate
                                 "
-                                [matTooltipPosition]="'above'"
+                                matTooltipPosition="above"
                                 color="accent"
                                 mat-icon-button
                             >
@@ -322,7 +325,7 @@
                                         : 'project-overview.under-review'
                                     ) | translate
                                 "
-                                [matTooltipPosition]="'above'"
+                                matTooltipPosition="above"
                                 color="accent"
                                 mat-icon-button
                             >
diff --git a/apps/red-ui/src/app/upload/upload-status-dialog/upload-status-overlay.component.html b/apps/red-ui/src/app/upload/upload-status-dialog/upload-status-overlay.component.html
index 3b67511a1..ba995fafd 100644
--- a/apps/red-ui/src/app/upload/upload-status-dialog/upload-status-overlay.component.html
+++ b/apps/red-ui/src/app/upload/upload-status-dialog/upload-status-overlay.component.html
@@ -18,7 +18,7 @@
             <div *ngFor="let model of uploadService.files" class="upload-list-item">
                 <div class="upload-line">
                     <div
-                        [matTooltipPosition]="'above'"
+                        matTooltipPosition="above"
                         [matTooltip]="model.file?.name"
                         class="upload-file-name"
                     >
@@ -36,7 +36,7 @@
                 </div>
                 <div *ngIf="model.completed && model.error" class="upload-line">
                     <div
-                        [matTooltipPosition]="'above'"
+                        matTooltipPosition="above"
                         [matTooltip]="model.error.message"
                         class="upload-file-name error"
                     >
@@ -47,7 +47,7 @@
                         <div
                             (click)="uploadItem(model)"
                             [matTooltip]="'upload-status.dialog.actions.re-upload' | translate"
-                            [matTooltipPosition]="'above'"
+                            matTooltipPosition="above"
                             class="error-action"
                         >
                             <mat-icon svgIcon="red:refresh"></mat-icon>
@@ -56,7 +56,7 @@
                         <div
                             (click)="cancelItem(model)"
                             [matTooltip]="'upload-status.dialog.actions.cancel' | translate"
-                            [matTooltipPosition]="'above'"
+                            matTooltipPosition="above"
                             class="error-action"
                         >
                             <mat-icon svgIcon="red:close"></mat-icon>
diff --git a/apps/red-ui/src/assets/i18n/en.json b/apps/red-ui/src/assets/i18n/en.json
index 6e8be4829..221819121 100644
--- a/apps/red-ui/src/assets/i18n/en.json
+++ b/apps/red-ui/src/assets/i18n/en.json
@@ -178,7 +178,6 @@
             "label": "Outdated",
             "toast": {
                 "message-project": "Some documents were not processed with the latest rule/dictionary set. They are marked with:\n\n",
-                "message-file": "This documents was not processed with the latest rule/dictionary set.\n\n",
                 "actions": {
                     "reanalyse-all": "Reanalyze all",
                     "reanalyse-file": "Reanalyze this file",
@@ -249,6 +248,7 @@
     "file-preview": {
         "show-redacted-view": "Show Redacted Preview",
         "cannot-show-redacted-view": "Redactions out of sync. Redacted Preview only available after reanalysis",
+        "reanalyse-notification": "This document was not processed with the latest rule/dictionary set. Reanalyse now to get updated annotations.",
         "reanalyse-file": "File reanalysis in progress... ",
         "view-toggle": "Redacted View",
         "tabs": {
diff --git a/apps/red-ui/src/assets/styles/red-button.scss b/apps/red-ui/src/assets/styles/red-button.scss
index 3e6f49608..ff39775b0 100644
--- a/apps/red-ui/src/assets/styles/red-button.scss
+++ b/apps/red-ui/src/assets/styles/red-button.scss
@@ -47,7 +47,11 @@
 .mat-icon-button {
     transition: background-color 0.25s ease-in-out;
 
-    &:hover {
+    &.warn {
+        background-color: $yellow-2;
+    }
+
+    &:hover:not(.warn) {
         background-color: $grey-2;
     }
 }
diff --git a/apps/red-ui/src/assets/styles/red-tooltips.scss b/apps/red-ui/src/assets/styles/red-tooltips.scss
index a26529fca..7a0fecf62 100644
--- a/apps/red-ui/src/assets/styles/red-tooltips.scss
+++ b/apps/red-ui/src/assets/styles/red-tooltips.scss
@@ -11,19 +11,29 @@
     position: relative;
     overflow: visible !important;
     text-align: center;
-}
 
-.mat-tooltip:after {
-    content: '';
-    position: absolute;
-    left: 50%;
-    margin-left: -5px;
-    width: 0;
-    height: 0;
-    z-index: 3000;
-    border-left: solid 5px transparent;
-    border-right: solid 5px transparent;
-    border-top: solid 6px $accent;
+    &:after {
+        content: '';
+        position: absolute;
+        left: 50%;
+        margin-left: -5px;
+        width: 0;
+        height: 0;
+        z-index: 3000;
+        border-left: solid 5px transparent;
+        border-right: solid 5px transparent;
+        border-top: solid 6px $accent;
+    }
+
+    &.warn {
+        background-color: $yellow-2;
+        text-align: initial;
+        color: $accent;
+
+        &:after {
+            border-top: solid 6px $yellow-2;
+        }
+    }
 }
 
 .mat-tooltip[style*='transform-origin: center top']:after {