diff --git a/packages/coding-agent/src/modes/skill-command.ts b/packages/coding-agent/src/modes/skill-command.ts
index 984fa110b..d8feaaaf2 100644
--- a/packages/coding-agent/src/modes/skill-command.ts
+++ b/packages/coding-agent/src/modes/skill-command.ts
@@ -1,3 +1,4 @@
+import type { ImageContent, TextContent } from "@oh-my-pi/pi-ai";
 import { type CustomMessage, SKILL_PROMPT_MESSAGE_TYPE, type SkillPromptDetails } from "../session/messages";
 import type { InteractiveModeContext } from "./types";
 
@@ -8,7 +9,7 @@ type SkillPromptMessage = Pick<
 	"customType" | "content" | "display" | "details" | "attribution"
 > & {
 	customType: typeof SKILL_PROMPT_MESSAGE_TYPE;
-	content: string;
+	content: string | (TextContent | ImageContent)[];
 	display: true;
 	details: SkillPromptDetails;
 	attribution: "user";
@@ -27,6 +28,7 @@ interface ParsedSkillCommand {
 interface InvokeSkillCommandOptions {
 	propagateErrors?: boolean;
 	queueOnly?: boolean;
+	images?: ImageContent[];
 }
 
 /** Built custom-message payload and delivery options for a `/skill:` command. */
@@ -55,6 +57,7 @@ export async function buildSkillCommandPrompt(
 	ctx: SkillCommandHost,
 	text: string,
 	streamingBehavior: "steer" | "followUp",
+	images?: ImageContent[],
 ): Promise<BuiltSkillCommandPrompt | undefined> {
 	const parsed = parseSkillCommand(text);
 	if (!parsed) return undefined;
@@ -68,6 +71,8 @@ export async function buildSkillCommandPrompt(
 		metaLines.push(`User: ${parsed.args}`);
 	}
 	const message = `${body}\n\n---\n\n${metaLines.join("\n")}`;
+	const textBlock: TextContent = { type: "text", text: message };
+	const promptContent = images && images.length > 0 ? [textBlock, ...images] : message;
 	const skillName = parsed.commandName.slice("skill:".length);
 	const details: SkillPromptDetails = {
 		name: skillName || parsed.commandName,
@@ -79,7 +84,7 @@ export async function buildSkillCommandPrompt(
 	return {
 		message: {
 			customType: SKILL_PROMPT_MESSAGE_TYPE,
-			content: message,
+			content: promptContent,
 			display: true,
 			details,
 			attribution: "user",
@@ -96,7 +101,7 @@ export async function invokeSkillCommandFromText(
 	options?: InvokeSkillCommandOptions,
 ): Promise<boolean> {
 	try {
-		const built = await buildSkillCommandPrompt(ctx, text, streamingBehavior);
+		const built = await buildSkillCommandPrompt(ctx, text, streamingBehavior, options?.images);
 		if (!built) return false;
 		const promptOptions = options?.queueOnly ? { ...built.options, queueOnly: true } : built.options;
 		await ctx.session.promptCustomMessage(built.message, promptOptions);
diff --git a/packages/coding-agent/src/modes/utils/ui-helpers.ts b/packages/coding-agent/src/modes/utils/ui-helpers.ts
index 4a831944d..ccc1599ad 100644
--- a/packages/coding-agent/src/modes/utils/ui-helpers.ts
+++ b/packages/coding-agent/src/modes/utils/ui-helpers.ts
@@ -672,6 +672,7 @@ export class UiHelpers {
 			await invokeSkillCommandFromText(this.ctx, message.text, message.mode, {
 				propagateErrors: true,
 				queueOnly: true,
+				images: message.images,
 			})
 		) {
 			return;
@@ -770,7 +771,12 @@ export class UiHelpers {
 			// is not sent as a literal prompt after compaction.
 			let promptPromise: Promise<unknown>;
 			if (isKnownSkillCommand(this.ctx, firstPrompt.text)) {
-				const built = await buildSkillCommandPrompt(this.ctx, firstPrompt.text, firstPrompt.mode);
+				const built = await buildSkillCommandPrompt(
+					this.ctx,
+					firstPrompt.text,
+					firstPrompt.mode,
+					firstPrompt.images,
+				);
 				promptPromise = built
 					? this.ctx.session.promptCustomMessage(built.message, built.options).catch(restoreQueue)
 					: Promise.resolve();
diff --git a/packages/coding-agent/test/input-controller-skill-queue.test.ts b/packages/coding-agent/test/input-controller-skill-queue.test.ts
index dbe8a899b..c4ee940a6 100644
--- a/packages/coding-agent/test/input-controller-skill-queue.test.ts
+++ b/packages/coding-agent/test/input-controller-skill-queue.test.ts
@@ -268,8 +268,9 @@ describe("compaction skill re-invocation", () => {
 	});
 
 	it("re-invokes a queued skill as a user-attributed skill prompt", async () => {
+		const image: ImageContent = { type: "image", data: "aGVsbG8=", mimeType: "image/png" };
 		const { ctx, promptCustomMessage, promptCustomMessageCalled, prompt, steer, followUp } =
-			createCompactionDrainContext([{ text: "/skill:test-skill arg1 arg2", mode: "followUp" }]);
+			createCompactionDrainContext([{ text: "/skill:test-skill arg1 arg2", mode: "followUp", images: [image] }]);
 		const uiHelpers = new UiHelpers(ctx);
 
 		await uiHelpers.flushCompactionQueue({ willRetry: false });
@@ -278,7 +279,11 @@ describe("compaction skill re-invocation", () => {
 		const [message, options] = firstPromptCustomCall(promptCustomMessage);
 		expect(message.customType).toBe(SKILL_PROMPT_MESSAGE_TYPE);
 		expect(message.attribution).toBe("user");
-		expect(message.content).toContain("Do the thing.");
+		if (!Array.isArray(message.content)) {
+			throw new Error("expected queued skill prompt to preserve image content blocks");
+		}
+		expect(message.content[0]).toMatchObject({ type: "text", text: expect.stringContaining("Do the thing.") });
+		expect(message.content[1]).toEqual(image);
 		expect(message.details).toMatchObject({ name: "test-skill", args: "arg1 arg2", lineCount: 1 });
 		expect(options).toEqual({
 			streamingBehavior: "followUp",
@@ -292,13 +297,22 @@ describe("compaction skill re-invocation", () => {
 	it("queues retry-drained skills without appending them to session history", async () => {
 		const fixture = await createRealSession();
 		try {
-			const { ctx } = createCompactionDrainContext([{ text: "/skill:test-skill retry args", mode: "followUp" }]);
+			const image: ImageContent = { type: "image", data: "cmV0cnk=", mimeType: "image/png" };
+			const { ctx } = createCompactionDrainContext([
+				{ text: "/skill:test-skill retry args", mode: "followUp", images: [image] },
+			]);
 			ctx.session = fixture.session;
 			const uiHelpers = new UiHelpers(ctx);
 
 			await uiHelpers.flushCompactionQueue({ willRetry: true });
 
 			expect(fixture.session.getQueuedMessages().followUp).toEqual(["/skill:test-skill retry args"]);
+			const queued = fixture.session.agent.peekFollowUpQueue()[0];
+			if (queued?.role !== "custom" || !Array.isArray(queued.content)) {
+				throw new Error("expected retry-drained skill to be queued as image-bearing custom content");
+			}
+			expect(queued.customType).toBe(SKILL_PROMPT_MESSAGE_TYPE);
+			expect(queued.content[1]).toEqual(image);
 			expect(fixture.session.messages).toEqual([]);
 		} finally {
 			await fixture.session.dispose();