diff --git a/webapp/channels/src/components/file_attachment/__snapshots__/file_attachment.test.tsx.snap b/webapp/channels/src/components/file_attachment/__snapshots__/file_attachment.test.tsx.snap
index 19b9dbc572c..161352fd1da 100644
--- a/webapp/channels/src/components/file_attachment/__snapshots__/file_attachment.test.tsx.snap
+++ b/webapp/channels/src/components/file_attachment/__snapshots__/file_attachment.test.tsx.snap
@@ -503,7 +503,7 @@ exports[`FileAttachment should match snapshot, with compact display 1`] = `
     class="post-image__column"
   >
     <div
-      class="post-image__details"
+      class="post-image__details compact"
     >
       <a
         class="post-image__name btn btn-icon btn-sm"
@@ -544,7 +544,11 @@ exports[`FileAttachment should match snapshot, with compact display 1`] = `
             </g>
           </svg>
         </span>
-        test.pdf
+        <span
+          class="post-image__filename"
+        >
+          test.pdf
+        </span>
       </a>
     </div>
   </div>
diff --git a/webapp/channels/src/components/file_attachment/__snapshots__/filename_overlay.test.tsx.snap b/webapp/channels/src/components/file_attachment/__snapshots__/filename_overlay.test.tsx.snap
index 2031fa83ab3..9616bfa8386 100644
--- a/webapp/channels/src/components/file_attachment/__snapshots__/filename_overlay.test.tsx.snap
+++ b/webapp/channels/src/components/file_attachment/__snapshots__/filename_overlay.test.tsx.snap
@@ -41,7 +41,11 @@ exports[`components/file_attachment/FilenameOverlay should match snapshot, compa
         </g>
       </svg>
     </span>
-    test_filename
+    <span
+      class="post-image__filename"
+    >
+      test_filename
+    </span>
   </a>
 </div>
 `;
diff --git a/webapp/channels/src/components/file_attachment/file_attachment.tsx b/webapp/channels/src/components/file_attachment/file_attachment.tsx
index be2c58fc451..e6746f79410 100644
--- a/webapp/channels/src/components/file_attachment/file_attachment.tsx
+++ b/webapp/channels/src/components/file_attachment/file_attachment.tsx
@@ -403,7 +403,7 @@ export default function FileAttachment(props: Props) {
                 ])}
             >
                 {fileThumbnail}
-                <div className='post-image__details'>
+                <div className={classNames('post-image__details', {compact: compactDisplay})}>
                     {fileDetail}
                     {fileActions}
                     {filenameOverlay}
diff --git a/webapp/channels/src/components/file_attachment/filename_overlay.tsx b/webapp/channels/src/components/file_attachment/filename_overlay.tsx
index 1ccf10b2778..0751ad6e0ac 100644
--- a/webapp/channels/src/components/file_attachment/filename_overlay.tsx
+++ b/webapp/channels/src/components/file_attachment/filename_overlay.tsx
@@ -78,7 +78,7 @@ export default class FilenameOverlay extends React.PureComponent<Props> {
                         rel='noopener noreferrer'
                     >
                         <AttachmentIcon className='icon'/>
-                        {trimmedFilename}
+                        <span className='post-image__filename'>{trimmedFilename}</span>
                     </a>
                 </WithTooltip>
             );
diff --git a/webapp/channels/src/components/file_preview/file_preview.test.tsx b/webapp/channels/src/components/file_preview/file_preview.test.tsx
index c1bca3d1687..17d9240adcf 100644
--- a/webapp/channels/src/components/file_preview/file_preview.test.tsx
+++ b/webapp/channels/src/components/file_preview/file_preview.test.tsx
@@ -149,4 +149,34 @@ describe('FilePreview', () => {
 
         expect(screen.getByAltText('file preview')).toHaveAttribute('src', getFileUrl(fileId));
     });
+
+    test('should add compact classes when compactMode is true', () => {
+        const props = {
+            ...baseProps,
+            compactMode: true,
+        };
+
+        const {container} = renderWithContext(
+            <FilePreview {...props}/>,
+        );
+
+        expect(container.querySelector('.file-preview.post-image__column.compact')).toBeInTheDocument();
+        expect(container.querySelector('.post-image__detail.compact')).toBeInTheDocument();
+        expect(container.querySelector('.file-preview__remove.compact')).toBeInTheDocument();
+    });
+
+    test('should not add compact classes when compactMode is false', () => {
+        const props = {
+            ...baseProps,
+            compactMode: false,
+        };
+
+        const {container} = renderWithContext(
+            <FilePreview {...props}/>,
+        );
+
+        expect(container.querySelector('.file-preview.post-image__column.compact')).not.toBeInTheDocument();
+        expect(container.querySelector('.post-image__detail.compact')).not.toBeInTheDocument();
+        expect(container.querySelector('.file-preview__remove.compact')).not.toBeInTheDocument();
+    });
 });
diff --git a/webapp/channels/src/components/file_preview/file_preview.tsx b/webapp/channels/src/components/file_preview/file_preview.tsx
index 85eba9c429f..cd08ca33f0d 100644
--- a/webapp/channels/src/components/file_preview/file_preview.tsx
+++ b/webapp/channels/src/components/file_preview/file_preview.tsx
@@ -1,6 +1,7 @@
 // Copyright (c) 2015-present Mattermost, Inc. All Rights Reserved.
 // See LICENSE.txt for license information.
 
+import classNames from 'classnames';
 import React from 'react';
 import type {ReactNode} from 'react';
 
@@ -28,7 +29,8 @@ type Props = {
     fileInfos: FilePreviewInfo[];
     uploadsInProgress?: string[];
     uploadsProgressPercent?: {[clientID: string]: FilePreviewInfo};
-}
+    compactMode?: boolean;
+};
 
 export default class FilePreview extends React.PureComponent<Props> {
     static defaultProps = {
@@ -85,6 +87,10 @@ export default class FilePreview extends React.PureComponent<Props> {
                 previewImage = <div className={'file-icon ' + Utils.getIconClassName(type)}/>;
             }
 
+            if (this.props.compactMode) {
+                className += ' compact';
+            }
+
             previews.push(
                 <div
                     key={info.id}
@@ -95,10 +101,10 @@ export default class FilePreview extends React.PureComponent<Props> {
                     </div>
                     <div className='post-image__details'>
                         <div className='post-image__detail_wrapper'>
-                            <div className='post-image__detail'>
+                            <div className={classNames('post-image__detail', {compact: this.props.compactMode})}>
                                 <FilenameOverlay
                                     fileInfo={info}
-                                    compactDisplay={false}
+                                    compactDisplay={this.props.compactMode}
                                     canDownload={false}
                                 />
                                 {info.extension && <span className='post-image__type'>{info.extension.toUpperCase()}</span>}
@@ -108,7 +114,7 @@ export default class FilePreview extends React.PureComponent<Props> {
                         <div>
                             {Boolean(this.props.onRemove) && (
                                 <a
-                                    className='file-preview__remove'
+                                    className={classNames('file-preview__remove', {compact: this.props.compactMode})}
                                     onClick={this.handleRemove.bind(this, info.id)}
                                 >
                                     <i className='icon icon-close'/>
@@ -138,7 +144,7 @@ export default class FilePreview extends React.PureComponent<Props> {
         }
 
         return (
-            <div className='file-preview__container'>
+            <div className={classNames('file-preview__container', {compact: this.props.compactMode})}>
                 {previews}
             </div>
         );
diff --git a/webapp/channels/src/components/file_preview/index.ts b/webapp/channels/src/components/file_preview/index.ts
index 58c441b7f8d..d08fe27b7b0 100644
--- a/webapp/channels/src/components/file_preview/index.ts
+++ b/webapp/channels/src/components/file_preview/index.ts
@@ -5,15 +5,19 @@ import {connect} from 'react-redux';
 
 import {getConfig} from 'mattermost-redux/selectors/entities/general';
 
+import {isCompactMode} from 'selectors/preferences';
+
 import type {GlobalState} from 'types/store';
 
 import FilePreview from './file_preview';
 
 function mapStateToProps(state: GlobalState) {
     const config = getConfig(state);
+    const compactMode = isCompactMode(state);
 
     return {
         enableSVGs: config.EnableSVGs === 'true',
+        compactMode,
     };
 }
 
diff --git a/webapp/channels/src/sass/components/_files.scss b/webapp/channels/src/sass/components/_files.scss
index 3bac076ceb7..5e81cac0fc2 100644
--- a/webapp/channels/src/sass/components/_files.scss
+++ b/webapp/channels/src/sass/components/_files.scss
@@ -15,6 +15,10 @@
     overflow-x: auto;
     overflow-y: hidden;
     white-space: nowrap;
+
+    &.compact {
+        height: unset;
+    }
 }
 
 .file-preview {
@@ -38,11 +42,20 @@
         margin-top: -16px;
         margin-left: -16px;
     }
+
+    &.compact {
+        overflow: hidden !important;
+    }
 }
 
 .app__body {
     .file-preview__remove {
         position: absolute;
+
+        &.compact {
+            position: unset;
+        }
+
         top: 4px;
         right: 4px;
         display: flex;
@@ -494,6 +507,12 @@
     font-size: 12px;
     text-align: left;
 
+    &.compact {
+        .post-image__name {
+            font-size: 12px;
+        }
+    }
+
     .post-image__archived-name {
         align-items: center;
         justify-content: start;
@@ -537,6 +556,14 @@
             line-height: normal;
             text-overflow: ellipsis;
 
+            &.compact {
+                height: unset;
+
+                .post-image__name {
+                    font-size: 12px;
+                }
+            }
+
             .post-image__name {
                 display: block;
                 overflow: hidden;
diff --git a/webapp/channels/src/sass/components/_post.scss b/webapp/channels/src/sass/components/_post.scss
index f366d92066f..08fe147268f 100644
--- a/webapp/channels/src/sass/components/_post.scss
+++ b/webapp/channels/src/sass/components/_post.scss
@@ -949,6 +949,7 @@
 
                 display: flex;
                 width: 100%;
+                max-width: 100%;
                 align-items: center;
                 justify-content: flex-start;
                 padding: 0 5px;
@@ -961,6 +962,12 @@
                     font-size: 0.9em;
                     opacity: 0.5;
                 }
+
+                .post-image__filename {
+                    display: inline;
+                    overflow: hidden;
+                    text-overflow: ellipsis;
+                }
             }
 
             a {
@@ -1673,11 +1680,11 @@
         }
     }
 
-    .post__translation-icon-processing {        
+    .post__translation-icon-processing {
         color: rgba(var(--center-channel-color-rgb), 0.73);
         font-size: 10px;
         line-height: 16px;
-        
+
         .LoadingSpinner.with-text .spinner {
             margin-right: 3px;
         }
diff --git a/webapp/channels/src/selectors/preferences.ts b/webapp/channels/src/selectors/preferences.ts
index 6749d88687f..7a254cbcd82 100644
--- a/webapp/channels/src/selectors/preferences.ts
+++ b/webapp/channels/src/selectors/preferences.ts
@@ -1,7 +1,7 @@
 // Copyright (c) 2015-present Mattermost, Inc. All Rights Reserved.
 // See LICENSE.txt for license information.
 
-import {getBool as getBoolPreference} from 'mattermost-redux/selectors/entities/preferences';
+import {get, getBool as getBoolPreference} from 'mattermost-redux/selectors/entities/preferences';
 
 import {Preferences} from 'utils/constants';
 
@@ -33,3 +33,12 @@ export const isUseMilitaryTime = (state: GlobalState) => {
         false,
     );
 };
+
+export const isCompactMode = (state: GlobalState) => {
+    return get(
+        state,
+        Preferences.CATEGORY_DISPLAY_SETTINGS,
+        Preferences.MESSAGE_DISPLAY,
+        Preferences.MESSAGE_DISPLAY_DEFAULT,
+    ) === Preferences.MESSAGE_DISPLAY_COMPACT;
+};