diff --git a/packages/server/src/server/agent/providers/claude/agent.test.ts b/packages/server/src/server/agent/providers/claude/agent.test.ts
index 118e93067c..4a9538d00a 100644
--- a/packages/server/src/server/agent/providers/claude/agent.test.ts
+++ b/packages/server/src/server/agent/providers/claude/agent.test.ts
@@ -17,7 +17,14 @@ import {
 } from "./agent.js";
 import { claudeProjectDirSync } from "./project-dir.js";
 import { streamSession } from "../test-utils/session-stream-adapter.js";
-import type { AgentSession, AgentTimelineItem, AgentStreamEvent } from "../../agent-sdk-types.js";
+import type {
+  AgentPromptInput,
+  AgentSession,
+  AgentTimelineItem,
+  AgentStreamEvent,
+} from "../../agent-sdk-types.js";
+import type { AgentAttachment } from "@getpaseo/protocol/messages";
+import { buildAgentPrompt, renderPromptAttachmentAsText } from "../../prompt-attachments.js";
 
 interface TestClaudeSession {
   translateMessageToEvents(message: SDKMessage): AgentStreamEvent[];
@@ -866,6 +873,97 @@ describe("ClaudeAgentSession features", () => {
     await session.close();
   });
 
+  async function captureSdkUserMessage(prompt: AgentPromptInput): Promise<SDKUserMessage> {
+    const { queryFactory, queryMock } = createQueryMock();
+    let resolveSent: ((message: SDKUserMessage) => void) | null = null;
+    const sent = new Promise<SDKUserMessage>((resolve) => {
+      resolveSent = resolve;
+    });
+    queryFactory.mockImplementation((input: { prompt: AsyncIterable<SDKUserMessage> }) => {
+      void (async () => {
+        for await (const message of input.prompt) {
+          resolveSent?.(message);
+          break;
+        }
+      })();
+      return queryMock;
+    });
+    const session = await new ClaudeAgentClient({
+      logger,
+      queryFactory,
+      resolveBinary: async () => "/test/claude/bin",
+    }).createSession({ provider: "claude", cwd: process.cwd() });
+    try {
+      await session.startTurn(prompt);
+      return await sent;
+    } finally {
+      await session.close();
+    }
+  }
+
+  const issueAttachment: AgentAttachment = {
+    type: "forge_issue",
+    mimeType: "application/paseo-forge-issue",
+    forge: "github",
+    number: 12,
+    title: "Fake issue for QA",
+    url: "https://example.invalid/acme/app/issues/12",
+    body: "This is an attached issue body.",
+  };
+
+  // Claude Code expands a slash command only when it is the last content block of the user
+  // message, so an auto-attached issue or a pasted screenshot must not be appended after it.
+  test("sends a typed slash command last when an attachment follows it", async () => {
+    const message = await captureSdkUserMessage(
+      buildAgentPrompt("/hello please", undefined, [issueAttachment]),
+    );
+
+    expect(message.message.content).toEqual([
+      { type: "text", text: renderPromptAttachmentAsText(issueAttachment) },
+      { type: "text", text: "/hello please" },
+    ]);
+  });
+
+  test("sends a typed slash command last when an image follows it", async () => {
+    const message = await captureSdkUserMessage(
+      buildAgentPrompt("/hello please", [{ data: "aGk=", mimeType: "image/png" }], undefined),
+    );
+
+    expect(message.message.content).toEqual([
+      { type: "image", source: { type: "base64", media_type: "image/png", data: "aGk=" } },
+      { type: "text", text: "/hello please" },
+    ]);
+  });
+
+  test("keeps typed text before attachments when it is not a slash command", async () => {
+    const message = await captureSdkUserMessage(
+      buildAgentPrompt("please look at this issue", undefined, [issueAttachment]),
+    );
+
+    expect(message.message.content).toEqual([
+      { type: "text", text: "please look at this issue" },
+      { type: "text", text: renderPromptAttachmentAsText(issueAttachment) },
+    ]);
+  });
+
+  test("moves the typed slash command, not an attachment that reads like one", async () => {
+    const chatHistory: AgentAttachment = {
+      type: "text",
+      mimeType: "text/plain",
+      contextKind: "chat_history",
+      text: "/earlier command quoted from another chat",
+    };
+    const message = await captureSdkUserMessage(
+      buildAgentPrompt("/hello please", undefined, [chatHistory, issueAttachment]),
+    );
+
+    expect(message.message.content).toEqual([
+      { type: "text", text: chatHistory.text },
+      { type: "text", text: renderPromptAttachmentAsText(issueAttachment) },
+      { type: "text", text: "/hello please" },
+    ]);
+  });
+
   test("maps Ultracode to xhigh effort and Claude ultracode settings", async () => {
     const { queryFactory } = createQueryMock();
     const client = new ClaudeAgentClient({
diff --git a/packages/server/src/server/agent/providers/claude/agent.ts b/packages/server/src/server/agent/providers/claude/agent.ts
index 496dfe2687..b23f58e244 100644
--- a/packages/server/src/server/agent/providers/claude/agent.ts
+++ b/packages/server/src/server/agent/providers/claude/agent.ts
@@ -3374,9 +3374,19 @@ class ClaudeAgentSession implements AgentSession {
           };
         }
     > = [];
+    // Claude Code expands a slash command only when it is the last content block of the user
+    // message. buildAgentPrompt places the typed text ahead of images and rendered attachments,
+    // so a "/command" sent with a pasted link or a screenshot would otherwise reach the model as
+    // literal text instead of the command it names.
+    let typedSlashCommandIndex = -1;
     if (Array.isArray(prompt)) {
       for (const chunk of prompt) {
         if (chunk.type === "text") {
+          // Attachments rendered as text always carry a mimeType; the composer's typed text does
+          // not. Only the typed block can be a slash command the user meant to invoke.
+          if (!("mimeType" in chunk) && this.parseSlashCommandInput(chunk.text)) {
+            typedSlashCommandIndex = content.length;
+          }
           content.push({ type: "text", text: chunk.text });
         } else if (chunk.type === "image") {
           if (isImageMimeType(chunk.mimeType)) {
@@ -3396,6 +3406,10 @@ class ClaudeAgentSession implements AgentSession {
     } else {
       content.push({ type: "text", text: prompt });
     }
+    if (typedSlashCommandIndex >= 0 && typedSlashCommandIndex < content.length - 1) {
+      const [slashCommand] = content.splice(typedSlashCommandIndex, 1);
+      content.push(slashCommand);
+    }
 
     const messageId = randomUUID();
     this.rememberUserMessageId(messageId);