diff --git a/packages/twenty-front/src/modules/activities/timeline-activities/rows/main-object/components/EventFieldDiffValueEffect.tsx b/packages/twenty-front/src/modules/activities/timeline-activities/rows/main-object/components/EventFieldDiffValueEffect.tsx
index c2fb1bf523..a9e924da59 100644
--- a/packages/twenty-front/src/modules/activities/timeline-activities/rows/main-object/components/EventFieldDiffValueEffect.tsx
+++ b/packages/twenty-front/src/modules/activities/timeline-activities/rows/main-object/components/EventFieldDiffValueEffect.tsx
@@ -1,9 +1,13 @@
-import { useEffect } from 'react';
+import { useContext, useEffect } from 'react';
 
-import { type FieldMetadataItem } from '@/object-metadata/types/FieldMetadataItem';
+import { TimelineActivityContext } from '@/activities/timeline-activities/contexts/TimelineActivityContext';
 import { type EnrichedObjectMetadataItem } from '@/object-metadata/types/EnrichedObjectMetadataItem';
+import { type FieldMetadataItem } from '@/object-metadata/types/FieldMetadataItem';
+import { type FieldFilesValue } from '@/object-record/record-field/ui/types/FieldMetadata';
 import { recordStoreFamilyState } from '@/object-record/record-store/states/recordStoreFamilyState';
+import { useAtomFamilyStateValue } from '@/ui/utilities/state/jotai/hooks/useAtomFamilyStateValue';
 import { useSetAtomFamilyState } from '@/ui/utilities/state/jotai/hooks/useSetAtomFamilyState';
+import { FieldMetadataType } from 'twenty-shared/types';
 import { isDefined } from 'twenty-shared/utils';
 
 export const EventFieldDiffValueEffect = ({
@@ -22,13 +26,39 @@ export const EventFieldDiffValueEffect = ({
     diffArtificialRecordStoreId,
   );
 
+  const { recordId } = useContext(TimelineActivityContext);
+  const recordStore = useAtomFamilyStateValue(recordStoreFamilyState, recordId);
+
   useEffect(() => {
     if (!isDefined(diffRecord)) return;
 
+    let fieldValue = diffRecord;
+
+    if (
+      fieldMetadataItem.type === FieldMetadataType.FILES &&
+      isDefined(recordStore) &&
+      Array.isArray(diffRecord)
+    ) {
+      const currentFiles = Array.isArray(recordStore[fieldMetadataItem.name])
+        ? (recordStore[fieldMetadataItem.name] as FieldFilesValue[])
+        : [];
+      const currentFileMap = new Map(
+        currentFiles.map((file) => [file.fileId, file]),
+      );
+
+      fieldValue = (diffRecord as FieldFilesValue[]).map((file) => {
+        const currentFile = currentFileMap.get(file.fileId);
+        if (isDefined(currentFile)) {
+          return { ...file, url: currentFile.url };
+        }
+        return { ...file, isDeleted: true, url: undefined };
+      });
+    }
+
     const forgedObjectRecord = {
       __typename: mainObjectMetadataItem.nameSingular,
       id: diffArtificialRecordStoreId,
-      [fieldMetadataItem.name]: diffRecord,
+      [fieldMetadataItem.name]: fieldValue,
     };
 
     setRecordStore(forgedObjectRecord);
@@ -36,8 +66,10 @@ export const EventFieldDiffValueEffect = ({
     diffRecord,
     diffArtificialRecordStoreId,
     fieldMetadataItem.name,
+    fieldMetadataItem.type,
     mainObjectMetadataItem.nameSingular,
     setRecordStore,
+    recordStore,
   ]);
 
   return <></>;
diff --git a/packages/twenty-front/src/modules/object-record/record-field/ui/types/FieldMetadata.ts b/packages/twenty-front/src/modules/object-record/record-field/ui/types/FieldMetadata.ts
index b51dabdf9b..bacd2a2b78 100644
--- a/packages/twenty-front/src/modules/object-record/record-field/ui/types/FieldMetadata.ts
+++ b/packages/twenty-front/src/modules/object-record/record-field/ui/types/FieldMetadata.ts
@@ -335,4 +335,5 @@ export type FieldFilesValue = {
   extension?: string;
   url?: string;
   fileCategory?: FileCategory;
+  isDeleted?: boolean;
 };
diff --git a/packages/twenty-front/src/modules/ui/field/display/components/FileChip.tsx b/packages/twenty-front/src/modules/ui/field/display/components/FileChip.tsx
index 3e110798fb..e313e5ebb5 100644
--- a/packages/twenty-front/src/modules/ui/field/display/components/FileChip.tsx
+++ b/packages/twenty-front/src/modules/ui/field/display/components/FileChip.tsx
@@ -1,4 +1,5 @@
 import { styled } from '@linaria/react';
+import { t } from '@lingui/core/macro';
 
 import { FileIcon } from '@/file/components/FileIcon';
 import { type FieldFilesValue } from '@/object-record/record-field/ui/types/FieldMetadata';
@@ -24,7 +25,8 @@ export const FileChip = ({
   onClick,
   forceDisableClick,
 }: FileChipProps) => {
-  const isClickable = forceDisableClick !== true;
+  const isDeleted = file.isDeleted === true;
+  const isClickable = forceDisableClick !== true && !isDeleted;
 
   const handleMouseDown = (event: React.MouseEvent): void => {
     if (!isClickable) {
@@ -45,17 +47,24 @@ export const FileChip = ({
   );
 
   return (
-    <StyledClickableContainer
-      clickable={isClickable}
-      onMouseDown={handleMouseDown}
-    >
-      <Chip
-        label={file.label ?? ''}
-        maxWidth={MAX_WIDTH}
-        leftComponent={fileIcon}
-        variant={ChipVariant.Highlighted}
+    <>
+      <StyledClickableContainer
         clickable={isClickable}
-      />
-    </StyledClickableContainer>
+        onMouseDown={handleMouseDown}
+      >
+        <Chip
+          label={file.label}
+          alwaysShowTooltip={isDeleted}
+          tooltipLabel={
+            isDeleted ? t`File no longer exists - ${file.label}` : undefined
+          }
+          disabled={isDeleted}
+          maxWidth={MAX_WIDTH}
+          leftComponent={fileIcon}
+          variant={isDeleted ? ChipVariant.Static : ChipVariant.Highlighted}
+          clickable={isClickable}
+        />
+      </StyledClickableContainer>
+    </>
   );
 };
diff --git a/packages/twenty-ui/src/components/chip/Chip.tsx b/packages/twenty-ui/src/components/chip/Chip.tsx
index 3ef7f9883b..fac19b24a4 100644
--- a/packages/twenty-ui/src/components/chip/Chip.tsx
+++ b/packages/twenty-ui/src/components/chip/Chip.tsx
@@ -29,6 +29,8 @@ export type ChipProps = {
   disabled?: boolean;
   clickable?: boolean;
   label: string;
+  tooltipLabel?: string;
+  alwaysShowTooltip?: boolean;
   isLabelHidden?: boolean;
   isBold?: boolean;
   maxWidth?: number;
@@ -172,6 +174,8 @@ const renderRightComponent = (
 export const Chip = ({
   size = ChipSize.Small,
   label,
+  tooltipLabel,
+  alwaysShowTooltip = false,
   isLabelHidden = false,
   isBold = false,
   disabled = false,
@@ -200,7 +204,12 @@ export const Chip = ({
     >
       {leftComponent}
       {!isLabelHidden && isDefined(label) && isNonEmptyString(label) ? (
-        <OverflowingTextWithTooltip size={size} text={label} />
+        <OverflowingTextWithTooltip
+          size={size}
+          text={label}
+          tooltipContent={tooltipLabel}
+          alwaysShowTooltip={alwaysShowTooltip}
+        />
       ) : !forceEmptyText && !isLabelHidden ? (
         <StyledDiv>{emptyLabel}</StyledDiv>
       ) : (
diff --git a/packages/twenty-ui/src/display/tooltip/OverflowingTextWithTooltip.tsx b/packages/twenty-ui/src/display/tooltip/OverflowingTextWithTooltip.tsx
index fcd0f5550a..21303f0426 100644
--- a/packages/twenty-ui/src/display/tooltip/OverflowingTextWithTooltip.tsx
+++ b/packages/twenty-ui/src/display/tooltip/OverflowingTextWithTooltip.tsx
@@ -3,8 +3,8 @@ import { type ReactNode, useRef, useState } from 'react';
 import { createPortal } from 'react-dom';
 
 import { isNonEmptyString } from '@sniptt/guards';
-import { isDefined } from 'twenty-shared/utils';
 import { themeCssVariables } from '@ui/theme-constants';
+import { isDefined } from 'twenty-shared/utils';
 import { AppTooltip, TooltipDelay } from './AppTooltip';
 
 const spacing4 = themeCssVariables.spacing[4];
@@ -64,6 +64,7 @@ type OverflowingTextWithTooltipProps = {
   isTooltipMultiline?: boolean;
   displayedMaxRows?: number;
   tooltipDelay?: TooltipDelay;
+  alwaysShowTooltip?: boolean;
 } & (
   | {
       text: string | null | undefined;
@@ -82,6 +83,7 @@ export const OverflowingTextWithTooltip = ({
   displayedMaxRows,
   tooltipContent,
   tooltipDelay = TooltipDelay.mediumDelay,
+  alwaysShowTooltip = false,
 }: OverflowingTextWithTooltipProps) => {
   const textElementId = `title-id-${+new Date()}`;
 
@@ -146,7 +148,7 @@ export const OverflowingTextWithTooltip = ({
       )}
 
       {shouldRenderTooltip &&
-        isTitleOverflowing &&
+        (isTitleOverflowing || alwaysShowTooltip) &&
         isDefined(tooltipText) &&
         createPortal(
           <div onClick={handleTooltipClick}>