diff --git a/blocksuite/affine/blocks/attachment/src/attachment-block.ts b/blocksuite/affine/blocks/attachment/src/attachment-block.ts
index bbf2b0b289..35d459f6c9 100644
--- a/blocksuite/affine/blocks/attachment/src/attachment-block.ts
+++ b/blocksuite/affine/blocks/attachment/src/attachment-block.ts
@@ -64,6 +64,11 @@ export class AttachmentBlockComponent extends CaptionedBlockComponent<Attachment
     return this.resourceController.blobUrl$.value;
   }
 
+  get filetype() {
+    const name = this.model.props.name$.value;
+    return name.split('.').pop() ?? '';
+  }
+
   protected containerStyleMap = styleMap({
     position: 'relative',
     width: '100%',
@@ -212,13 +217,23 @@ export class AttachmentBlockComponent extends CaptionedBlockComponent<Attachment
     );
   };
 
-  protected renderReloadButton = () => {
+  protected renderNormalButton = (needUpload: boolean) => {
+    const label = needUpload ? 'retry' : 'reload';
+    const run = async () => {
+      if (needUpload) {
+        await this.resourceController.upload();
+        return;
+      }
+
+      this.refreshData();
+    };
+
     return html`
       <button
         class="affine-attachment-content-button"
         @click=${(event: MouseEvent) => {
           event.stopPropagation();
-          this.refreshData();
+          run().catch(console.error);
 
           {
             const mode =
@@ -230,21 +245,28 @@ export class AttachmentBlockComponent extends CaptionedBlockComponent<Attachment
                 segment,
                 page: `${segment} editor`,
                 module: 'attachment',
-                control: 'reload',
+                control: label,
                 category: 'card',
-                type: this.model.props.name.split('.').pop() ?? '',
+                type: this.filetype,
               });
           }
         }}
       >
-        ${ResetIcon()} Reload
+        ${ResetIcon()} ${label}
       </button>
     `;
   };
 
   protected renderWithHorizontal(
     classInfo: ClassInfo,
-    { icon, title, description, kind, state }: AttachmentResolvedStateInfo
+    {
+      icon,
+      title,
+      description,
+      kind,
+      state,
+      needUpload,
+    }: AttachmentResolvedStateInfo
   ) {
     return html`
       <div class=${classMap(classInfo)}>
@@ -261,7 +283,7 @@ export class AttachmentBlockComponent extends CaptionedBlockComponent<Attachment
               ${description}
             </div>
             ${choose(state, [
-              ['error', this.renderReloadButton],
+              ['error', () => this.renderNormalButton(needUpload)],
               ['error:oversize', this.renderUpgradeButton],
             ])}
           </div>
@@ -274,7 +296,14 @@ export class AttachmentBlockComponent extends CaptionedBlockComponent<Attachment
 
   protected renderWithVertical(
     classInfo: ClassInfo,
-    { icon, title, description, kind, state }: AttachmentResolvedStateInfo
+    {
+      icon,
+      title,
+      description,
+      kind,
+      state,
+      needUpload,
+    }: AttachmentResolvedStateInfo
   ) {
     return html`
       <div class=${classMap(classInfo)}>
@@ -294,7 +323,7 @@ export class AttachmentBlockComponent extends CaptionedBlockComponent<Attachment
         <div class="affine-attachment-banner">
           ${kind}
           ${choose(state, [
-            ['error', this.renderReloadButton],
+            ['error', () => this.renderNormalButton(needUpload)],
             ['error:oversize', this.renderUpgradeButton],
           ])}
         </div>
@@ -305,7 +334,7 @@ export class AttachmentBlockComponent extends CaptionedBlockComponent<Attachment
   protected resolvedState$ = computed<AttachmentResolvedStateInfo>(() => {
     const size = this.model.props.size;
     const name = this.model.props.name$.value;
-    const kind = getAttachmentFileIcon(name.split('.').pop() ?? '');
+    const kind = getAttachmentFileIcon(this.filetype);
 
     const resolvedState = this.resourceController.resolveStateWith({
       loadingIcon: LoadingIcon(),
@@ -359,11 +388,16 @@ export class AttachmentBlockComponent extends CaptionedBlockComponent<Attachment
         const message = resolvedState.description;
         if (!message) return null;
 
+        const needUpload = resolvedState.needUpload;
+        const action = () =>
+          needUpload ? this.resourceController.upload() : this.reload();
+
         return html`
           <affine-resource-status
             class="affine-attachment-embed-status"
             .message=${message}
-            .reload=${() => this.reload()}
+            .needUpload=${needUpload}
+            .action=${action}
           ></affine-resource-status>
         `;
       })}
@@ -372,10 +406,10 @@ export class AttachmentBlockComponent extends CaptionedBlockComponent<Attachment
 
   private readonly _renderCitation = () => {
     const { name, footnoteIdentifier } = this.model.props;
-    const fileType = name.split('.').pop() ?? '';
-    const fileTypeIcon = getAttachmentFileIcon(fileType);
+    const icon = getAttachmentFileIcon(this.filetype);
+
     return html`<affine-citation-card
-      .icon=${fileTypeIcon}
+      .icon=${icon}
       .citationTitle=${name}
       .citationIdentifier=${footnoteIdentifier}
       .active=${this.selected$.value}
diff --git a/blocksuite/affine/blocks/attachment/src/styles.ts b/blocksuite/affine/blocks/attachment/src/styles.ts
index d13cbb6fe0..e504a03739 100644
--- a/blocksuite/affine/blocks/attachment/src/styles.ts
+++ b/blocksuite/affine/blocks/attachment/src/styles.ts
@@ -91,6 +91,7 @@ export const styles = css`
     font-size: var(--affine-font-xs);
     font-style: normal;
     font-weight: 500;
+    text-transform: capitalize;
     line-height: 20px;
 
     svg {
diff --git a/blocksuite/affine/blocks/image/src/components/page-image-block.ts b/blocksuite/affine/blocks/image/src/components/page-image-block.ts
index 9e0c831a2a..5d21875e03 100644
--- a/blocksuite/affine/blocks/image/src/components/page-image-block.ts
+++ b/blocksuite/affine/blocks/image/src/components/page-image-block.ts
@@ -359,7 +359,9 @@ export class ImageBlockPageComponent extends SignalWatcher(
       ? ImageSelectedRect(this._doc.readonly)
       : null;
 
-    const { loading, error, icon, description } = this.state;
+    const blobUrl = this.block.blobUrl;
+    const caption = this.block.model.props.caption$.value ?? 'Image';
+    const { loading, error, icon, description, needUpload } = this.state;
 
     return html`
       <div class="resizable-img" style=${styleMap(imageSize)}>
@@ -367,8 +369,8 @@ export class ImageBlockPageComponent extends SignalWatcher(
           class="drag-target"
           draggable="false"
           loading="lazy"
-          src=${this.block.blobUrl}
-          alt=${this.block.model.props.caption$.value ?? 'Image'}
+          src=${blobUrl}
+          alt=${caption}
           @error=${this._handleError}
         />
 
@@ -377,12 +379,16 @@ export class ImageBlockPageComponent extends SignalWatcher(
 
       ${when(loading, () => html`<div class="loading">${icon}</div>`)}
       ${when(
-        error && description,
+        Boolean(error && description),
         () =>
           html`<affine-resource-status
             class="affine-image-status"
             .message=${description}
-            .reload=${() => this.block.refreshData()}
+            .needUpload=${needUpload}
+            .action=${() =>
+              needUpload
+                ? this.block.resourceController.upload()
+                : this.block.refreshData()}
           ></affine-resource-status>`
       )}
     `;
diff --git a/blocksuite/affine/blocks/image/src/image-edgeless-block.ts b/blocksuite/affine/blocks/image/src/image-edgeless-block.ts
index 43ddc01373..4dacc45e70 100644
--- a/blocksuite/affine/blocks/image/src/image-edgeless-block.ts
+++ b/blocksuite/affine/blocks/image/src/image-edgeless-block.ts
@@ -137,6 +137,8 @@ export class ImageEdgelessBlockComponent extends GfxBlockComponent<ImageBlockMod
       description: formatSize(size),
     });
 
+    const { loading, icon, description, error, needUpload } = resovledState;
+
     return html`
       <div class="affine-image-container" style=${containerStyleMap}>
         ${when(
@@ -152,17 +154,18 @@ export class ImageEdgelessBlockComponent extends GfxBlockComponent<ImageBlockMod
                 @error=${this._handleError}
               />
             </div>
+            ${when(loading, () => html`<div class="loading">${icon}</div>`)}
             ${when(
-              resovledState.loading,
-              () => html`<div class="loading">${resovledState.icon}</div>`
-            )}
-            ${when(
-              resovledState.error && resovledState.description,
+              Boolean(error && description),
               () =>
                 html`<affine-resource-status
                   class="affine-image-status"
-                  .message=${resovledState.description}
-                  .reload=${() => this.refreshData()}
+                  .message=${description}
+                  .needUpload=${needUpload}
+                  .action=${() =>
+                    needUpload
+                      ? this.resourceController.upload()
+                      : this.refreshData()}
                 ></affine-resource-status>`
             )}
           `,
diff --git a/blocksuite/affine/components/src/resource/resource.ts b/blocksuite/affine/components/src/resource/resource.ts
index 60efd2df92..bca8fc77a7 100644
--- a/blocksuite/affine/components/src/resource/resource.ts
+++ b/blocksuite/affine/components/src/resource/resource.ts
@@ -28,6 +28,7 @@ export type ResolvedStateInfoPart = {
   error: boolean;
   state: StateKind;
   url: string | null;
+  needUpload: boolean;
 };
 
 export type ResolvedStateInfo = StateInfo & ResolvedStateInfoPart;
@@ -41,6 +42,7 @@ export class ResourceController implements Disposable {
   readonly resolvedState$ = computed<ResolvedStateInfoPart>(() => {
     const url = this.blobUrl$.value;
     const {
+      needUpload = false,
       uploading = false,
       downloading = false,
       overSize = false,
@@ -57,7 +59,13 @@ export class ResourceController implements Disposable {
 
     const loading = state === 'uploading' || state === 'loading';
 
-    return { error: hasError, loading, state, url };
+    return {
+      error: hasError,
+      needUpload,
+      loading,
+      state,
+      url,
+    };
   });
 
   private engine?: BlobEngine;
@@ -92,7 +100,8 @@ export class ResourceController implements Disposable {
       errorIcon?: TemplateResult;
     } & StateInfo
   ): ResolvedStateInfo {
-    const { error, loading, state, url } = this.resolvedState$.value;
+    const { error, loading, state, url, needUpload } =
+      this.resolvedState$.value;
 
     const { icon, title, description, loadingIcon, errorIcon } = info;
 
@@ -104,11 +113,11 @@ export class ResourceController implements Disposable {
       title,
       description,
       url,
+      needUpload,
     };
 
     if (loading) {
       result.icon = loadingIcon ?? icon;
-      result.title = state === 'uploading' ? 'Uploading...' : 'Loading...';
     } else if (error) {
       result.icon = errorIcon ?? icon;
       result.description = this.state$.value.errorMessage ?? description;
@@ -130,13 +139,15 @@ export class ResourceController implements Disposable {
       if (!blobState$) return;
 
       const subscription = blobState$.subscribe(state => {
-        let { uploading, downloading } = state;
-        if (state.overSize || state.errorMessage) {
+        let { uploading, downloading, errorMessage } = state;
+        if (state.overSize) {
           uploading = false;
           downloading = false;
+        } else if ((uploading || downloading) && errorMessage) {
+          errorMessage = null;
         }
 
-        this.updateState({ ...state, uploading, downloading });
+        this.updateState({ ...state, uploading, downloading, errorMessage });
       });
 
       return () => subscription.unsubscribe();
@@ -178,6 +189,9 @@ export class ResourceController implements Disposable {
   }
 
   async refreshUrlWith(type?: string) {
+    // Resets the state.
+    this.state$.value = {};
+
     const url = await this.createUrlWith(type);
     if (!url) return;
 
@@ -191,6 +205,21 @@ export class ResourceController implements Disposable {
     URL.revokeObjectURL(prevUrl);
   }
 
+  // Re-upload to the server.
+  async upload() {
+    const blobId = this.blobId$.peek();
+    if (!blobId) return;
+
+    const state = this.state$.peek();
+    if (!state.needUpload) return;
+    if (state.uploading) return;
+
+    // Resets the state.
+    this.state$.value = {};
+
+    return await this.engine?.upload(blobId);
+  }
+
   dispose() {
     const url = this.blobUrl$.peek();
     if (!url) return;
diff --git a/blocksuite/affine/components/src/resource/status.ts b/blocksuite/affine/components/src/resource/status.ts
index e6a239d637..9c81cc09a4 100644
--- a/blocksuite/affine/components/src/resource/status.ts
+++ b/blocksuite/affine/components/src/resource/status.ts
@@ -2,7 +2,7 @@ import {
   fontBaseStyle,
   panelBaseColorsStyle,
 } from '@blocksuite/affine-shared/styles';
-import { unsafeCSSVarV2 } from '@blocksuite/affine-shared/theme';
+import { unsafeCSSVar, unsafeCSSVarV2 } from '@blocksuite/affine-shared/theme';
 import {
   createButtonPopper,
   stopPropagation,
@@ -15,7 +15,8 @@ import { property, query } from 'lit/decorators.js';
 
 @requiredProperties({
   message: PropTypes.string,
-  reload: PropTypes.instanceOf(Function),
+  needUpload: PropTypes.boolean,
+  action: PropTypes.instanceOf(Function),
 })
 export class ResourceStatus extends WithDisposable(LitElement) {
   static override styles = css`
@@ -32,7 +33,7 @@ export class ResourceStatus extends WithDisposable(LitElement) {
       cursor: pointer;
       color: ${unsafeCSSVarV2('button/pureWhiteText')};
       background: ${unsafeCSSVarV2('status/error')};
-      box-shadow: var(--affine-overlay-shadow);
+      box-shadow: ${unsafeCSSVar('overlayShadow')};
     }
 
     ${panelBaseColorsStyle('.popper')}
@@ -43,28 +44,36 @@ export class ResourceStatus extends WithDisposable(LitElement) {
       padding: 8px;
       border-radius: 8px;
       width: 260px;
-      font-size: var(--affine-font-sm);
       font-style: normal;
       font-weight: 400;
       line-height: 22px;
+      font-size: ${unsafeCSSVar('fontSm')};
 
       &[data-show] {
         display: flex;
         flex-direction: column;
-        gap: 8px;
+        gap: 4px;
       }
     }
 
+    .header {
+      font-weight: 500;
+    }
+
     .content {
+      font-feature-settings:
+        'liga' off,
+        'clig' off;
       color: ${unsafeCSSVarV2('text/primary')};
     }
 
     .footer {
       display: flex;
       justify-content: flex-end;
+      margin-top: 4px;
     }
 
-    button.reload {
+    button.action {
       display: flex;
       align-items: center;
       padding: 2px 12px;
@@ -102,23 +111,35 @@ export class ResourceStatus extends WithDisposable(LitElement) {
       this._popper?.toggle();
     });
     this.disposables.addFromEvent(
-      this._reloadButton,
+      this._actionButton,
       'click',
       (_: MouseEvent) => {
         this._popper?.hide();
-        this.reload();
+        this.action();
       }
     );
     this.disposables.add(() => this._popper?.dispose());
   }
 
   override render() {
+    const { message, needUpload } = this;
+    const { type, label } = needUpload
+      ? {
+          type: 'Upload',
+          label: 'Retry',
+        }
+      : {
+          type: 'Download',
+          label: 'Reload',
+        };
+
     return html`
       <button class="status">${InformationIcon()}</button>
       <div class="popper">
-        <div class="content">${this.message}</div>
+        <div class="header">${type} failed</div>
+        <div class="content">${message}</div>
         <div class="footer">
-          <button class="reload">Reload</button>
+          <button class="action">${label}</button>
         </div>
       </div>
     `;
@@ -130,12 +151,15 @@ export class ResourceStatus extends WithDisposable(LitElement) {
   @query('button.status')
   private accessor _trigger!: HTMLButtonElement;
 
-  @query('button.reload')
-  private accessor _reloadButton!: HTMLButtonElement;
+  @query('button.action')
+  private accessor _actionButton!: HTMLButtonElement;
 
   @property({ attribute: false })
   accessor message!: string;
 
   @property({ attribute: false })
-  accessor reload!: () => void;
+  accessor needUpload!: boolean;
+
+  @property({ attribute: false })
+  accessor action!: () => void;
 }
diff --git a/blocksuite/affine/shared/src/services/telemetry-service/types.ts b/blocksuite/affine/shared/src/services/telemetry-service/types.ts
index 71141175be..0917e91cbd 100644
--- a/blocksuite/affine/shared/src/services/telemetry-service/types.ts
+++ b/blocksuite/affine/shared/src/services/telemetry-service/types.ts
@@ -65,7 +65,7 @@ export interface AttachmentReloadedEvent extends TelemetryEvent {
   page: 'doc editor' | 'whiteboard editor';
   segment: 'doc' | 'whiteboard';
   module: 'attachment';
-  control: 'reload';
+  control: 'reload' | 'retry';
   category: 'card' | 'embed';
   type: string; // file type
 }
diff --git a/blocksuite/framework/sync/src/blob/engine.ts b/blocksuite/framework/sync/src/blob/engine.ts
index 89546eebab..f8a66a6815 100644
--- a/blocksuite/framework/sync/src/blob/engine.ts
+++ b/blocksuite/framework/sync/src/blob/engine.ts
@@ -108,6 +108,10 @@ export class BlobEngine {
     return this.main.blobState$?.(key) ?? null;
   }
 
+  upload(key: string) {
+    return this.main.upload?.(key) ?? null;
+  }
+
   start() {
     if (this._abort) {
       return;
diff --git a/blocksuite/framework/sync/src/blob/source.ts b/blocksuite/framework/sync/src/blob/source.ts
index 6cf9239df4..3dd3cef1d1 100644
--- a/blocksuite/framework/sync/src/blob/source.ts
+++ b/blocksuite/framework/sync/src/blob/source.ts
@@ -5,6 +5,8 @@ export interface BlobState {
   downloading: boolean;
   errorMessage?: string | null;
   overSize: boolean;
+  needUpload: boolean;
+  needDownload: boolean;
 }
 
 export interface BlobSource {
@@ -16,4 +18,6 @@ export interface BlobSource {
   list: () => Promise<string[]>;
   // This state is only available when uploading to the server or downloading from the server.
   blobState$?: (key: string) => Observable<BlobState> | null;
+  // Re-upload to the server.
+  upload?: (key: string) => Promise<boolean>;
 }
diff --git a/blocksuite/playground/apps/_common/sync/blob/mock-server.ts b/blocksuite/playground/apps/_common/sync/blob/mock-server.ts
index a9600522fc..05590f3d74 100644
--- a/blocksuite/playground/apps/_common/sync/blob/mock-server.ts
+++ b/blocksuite/playground/apps/_common/sync/blob/mock-server.ts
@@ -112,7 +112,13 @@ export class MockServerBlobSource implements BlobSource {
 }
 
 function defaultState(): BlobState {
-  return { uploading: false, downloading: false, overSize: false };
+  return {
+    uploading: false,
+    downloading: false,
+    overSize: false,
+    needDownload: false,
+    needUpload: false,
+  };
 }
 
 function nextState(
diff --git a/packages/frontend/core/src/modules/workspace/entities/workspace.ts b/packages/frontend/core/src/modules/workspace/entities/workspace.ts
index 7982bc1408..535735d3ea 100644
--- a/packages/frontend/core/src/modules/workspace/entities/workspace.ts
+++ b/packages/frontend/core/src/modules/workspace/entities/workspace.ts
@@ -58,6 +58,7 @@ export class Workspace extends Entity {
           },
           /* eslint-disable rxjs/finnish */
           blobState$: key => this.engine.blob.blobState$(key),
+          upload: key => this.engine.blob.upload(key),
           name: 'blob',
           readonly: false,
         },