diff --git a/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentWidgets.ts b/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentWidgets.ts
index 0773c51da91acb..e97d9c5b1a8b84 100644
--- a/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentWidgets.ts
+++ b/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentWidgets.ts
@@ -538,9 +538,20 @@ export class ImageAttachmentWidget extends AbstractChatAttachmentWidget {
 		const currentLanguageModelName = this.currentLanguageModel ? this.languageModelsService.lookupLanguageModel(this.currentLanguageModel.identifier)?.name ?? this.currentLanguageModel.identifier : 'Current model';
 
 		const fullName = resource ? this.labelService.getUriLabel(resource) : (attachment.fullName || attachment.name);
-		this._register(createImageElements(resource, attachment.name, fullName, this.element, imageData ?? (attachment.value as Uint8Array), attachment.id, this.hoverService, ariaLabel, currentLanguageModelName, clickHandler, this.currentLanguageModel, omittedState));
+
+		const imageElements = this._register(new MutableDisposable<IDisposable>());
+		const renderImageElements = (buffer: Uint8Array) => {
+			imageElements.value = createImageElements(resource, attachment.name, fullName, this.element, buffer, attachment.id, this.hoverService, ariaLabel, currentLanguageModelName, clickHandler, this.currentLanguageModel, omittedState);
+			// createImageElements resets the label; restore the deletion hint after each render.
+			this.element.ariaLabel = this.appendDeletionHint(ariaLabel);
+		};
+		renderImageElements(imageData ?? new Uint8Array());
+
+		// Hydrated attachments need disk bytes so the preview does not fall back to a generic file icon.
+		if (!imageData && resource && omittedState !== OmittedState.Full && omittedState !== OmittedState.ImageLimitExceeded) {
+			void this.loadImageBytes(resource, renderImageElements);
+		}
 		this.attachSaveButton(resource, imageData, attachment.name, options.supportsDeletion);
-		this.element.ariaLabel = this.appendDeletionHint(ariaLabel);
 
 		// Wire up click + keyboard (Enter/Space) open handlers
 		const canOpenCarousel = !!imageData && configurationService.getValue<boolean>(ChatConfiguration.ImageCarouselEnabled);
@@ -558,6 +569,20 @@ export class ImageAttachmentWidget extends AbstractChatAttachmentWidget {
 		}
 	}
 
+	private async loadImageBytes(resource: URI, render: (buffer: Uint8Array) => void): Promise<void> {
+		let content: VSBuffer;
+		try {
+			content = (await this.fileService.readFile(resource)).value;
+		} catch {
+			// The file may no longer exist; keep the icon fallback that is already rendered.
+			return;
+		}
+		if (this._store.isDisposed) {
+			return;
+		}
+		render(content.buffer);
+	}
+
 	private async openInCarousel(id: string, name: string, data: Uint8Array | undefined, referenceUri: URI | undefined, preferCurrentInput: boolean | undefined): Promise<void> {
 		const resource = referenceUri ?? URI.from({ scheme: 'data', path: `${id}/${encodeURIComponent(name)}` });
 		await this.chatImageCarouselService.openCarouselAtResource(resource, data, { preferCurrentInput });
@@ -723,6 +748,13 @@ function createImageElements(resource: URI | undefined, name: string, fullName:
 			hoverElement.appendChild(dom.$('div', undefined, localize('chat.autoImageAttachmentHover', "Image support depends on the model selected by Auto.")));
 		}
 	}
+
+	// Remove old DOM so the widget can safely re-render after hydrated bytes load.
+	disposable.add(toDisposable(() => {
+		currentPill.remove();
+		textLabel.remove();
+	}));
+
 	return disposable;
 }
 
diff --git a/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatAttachmentsContentPart.test.ts b/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatAttachmentsContentPart.test.ts
index fdaa407bed504d..15b98f1d43ab63 100644
--- a/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatAttachmentsContentPart.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatAttachmentsContentPart.test.ts
@@ -9,8 +9,10 @@ import { mainWindow } from '../../../../../../../base/browser/window.js';
 import { URI } from '../../../../../../../base/common/uri.js';
 import { ExtensionIdentifier } from '../../../../../../../platform/extensions/common/extensions.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../../base/test/common/utils.js';
-import { workbenchInstantiationService } from '../../../../../../test/browser/workbenchTestServices.js';
-import { getEffectiveImageOmittedState } from '../../../../browser/attachments/chatAttachmentWidgets.js';
+import { IFileService } from '../../../../../../../platform/files/common/files.js';
+import { TestFileService, workbenchInstantiationService } from '../../../../../../test/browser/workbenchTestServices.js';
+import { DEFAULT_LABELS_CONTAINER, ResourceLabels } from '../../../../../../browser/labels.js';
+import { getEffectiveImageOmittedState, ImageAttachmentWidget } from '../../../../browser/attachments/chatAttachmentWidgets.js';
 import { ChatAttachmentsContentPart } from '../../../../browser/widget/chatContentParts/chatAttachmentsContentPart.js';
 import { AgentHostCompletionReferenceKind, IChatRequestVariableEntry, OmittedState, toAgentHostCompletionVariableEntry } from '../../../../common/attachments/chatVariableEntries.js';
 import { ILanguageModelChatMetadata, ILanguageModelsService } from '../../../../common/languageModels.js';
@@ -347,5 +349,82 @@ suite('ChatAttachmentsContentPart', () => {
 
 			assert.strictEqual(getEffectiveImageOmittedState(OmittedState.Full, autoModel, true), OmittedState.NotOmitted);
 		});
+
+		suite('hydrated image attachments', () => {
+			async function renderImageAndCollectReads(image: IChatRequestVariableEntry): Promise<string[]> {
+				const fileService = instantiationService.get(IFileService) as TestFileService;
+				const part = store.add(instantiationService.createInstance(
+					ChatAttachmentsContentPart,
+					{ variables: [image] }
+				));
+
+				mainWindow.document.body.appendChild(part.domNode!);
+				disposables.add(toDisposable(() => part.domNode?.remove()));
+
+				// Let the widget's lazy byte load (a microtask) settle before inspecting reads.
+				await new Promise<void>(resolve => setTimeout(resolve, 0));
+
+				return fileService.readOperations.map(read => read.resource.toString());
+			}
+
+			test('should load bytes from the resource for a hydrated (uri-only) image', async () => {
+				const resource = URI.file('/test/pasted-image.png');
+				const reads = await renderImageAndCollectReads({
+					kind: 'image',
+					id: 'hydrated-image',
+					name: 'pasted-image.png',
+					value: resource,
+					mimeType: 'image/png',
+					isURL: true,
+					references: [{ kind: 'reference', reference: resource }]
+				});
+
+				assert.deepStrictEqual(reads, [resource.toString()]);
+			});
+
+			test('should not read the resource for an image with inline bytes', async () => {
+				const resource = URI.file('/test/inline-image.png');
+				const reads = await renderImageAndCollectReads({
+					kind: 'image',
+					id: 'inline-image',
+					name: 'inline-image.png',
+					value: new Uint8Array([0x89, 0x50, 0x4E, 0x47]),
+					mimeType: 'image/png',
+					isURL: false,
+					references: [{ kind: 'reference', reference: resource }]
+				});
+
+				assert.deepStrictEqual(reads, []);
+			});
+
+			test('should keep delete hint after loading hydrated image bytes', async () => {
+				const resource = URI.file('/test/pasted-image.png');
+				const container = mainWindow.document.createElement('div');
+				mainWindow.document.body.appendChild(container);
+				disposables.add(toDisposable(() => container.remove()));
+				const contextResourceLabels = disposables.add(instantiationService.createInstance(ResourceLabels, DEFAULT_LABELS_CONTAINER));
+				const widget = disposables.add(instantiationService.createInstance(
+					ImageAttachmentWidget,
+					resource,
+					{
+						kind: 'image',
+						id: 'hydrated-image-with-delete',
+						name: 'pasted-image.png',
+						value: resource,
+						mimeType: 'image/png',
+						isURL: true,
+						references: [{ kind: 'reference', reference: resource }]
+					},
+					undefined,
+					{ shouldFocusClearButton: false, supportsDeletion: true },
+					container,
+					contextResourceLabels
+				));
+
+				await new Promise<void>(resolve => setTimeout(resolve, 0));
+
+				assert.strictEqual(widget.element.ariaLabel, 'Attached image, pasted-image.png (Delete)');
+			});
+		});
 	});
 });