diff --git a/tests/tui_gateway/test_protocol.py b/tests/tui_gateway/test_protocol.py
index 43f2b5a16..eb51cccfe 100644
--- a/tests/tui_gateway/test_protocol.py
+++ b/tests/tui_gateway/test_protocol.py
@@ -245,7 +245,7 @@ def test_slash_exec_rejects_skill_commands(server):
     # Mock scan_skill_commands to return a known skill
     fake_skills = {"/hermes-agent-dev": {"name": "hermes-agent-dev", "description": "Dev workflow"}}
 
-    with patch("agent.skill_commands.scan_skill_commands", return_value=fake_skills):
+    with patch("agent.skill_commands.get_skill_commands", return_value=fake_skills):
         resp = server.handle_request({
             "id": "r1",
             "method": "slash.exec",
@@ -324,6 +324,90 @@ def test_command_dispatch_steer_fallback_sends_message(server):
     assert result["message"] == "focus on testing"
 
 
+def test_command_dispatch_retry_finds_last_user_message(server):
+    """command.dispatch /retry walks session['history'] to find the last user message."""
+    sid = "test-session"
+    history = [
+        {"role": "user", "content": "first question"},
+        {"role": "assistant", "content": "first answer"},
+        {"role": "user", "content": "second question"},
+        {"role": "assistant", "content": "second answer"},
+    ]
+    server._sessions[sid] = {
+        "session_key": sid,
+        "agent": None,
+        "history": history,
+        "history_lock": threading.Lock(),
+        "history_version": 0,
+    }
+
+    resp = server.handle_request({
+        "id": "r4",
+        "method": "command.dispatch",
+        "params": {"name": "retry", "session_id": sid},
+    })
+
+    assert "error" not in resp
+    result = resp["result"]
+    assert result["type"] == "send"
+    assert result["message"] == "second question"
+    # Verify history was truncated: everything from last user message onward removed
+    assert len(server._sessions[sid]["history"]) == 2
+    assert server._sessions[sid]["history"][-1]["role"] == "assistant"
+    assert server._sessions[sid]["history_version"] == 1
+
+
+def test_command_dispatch_retry_empty_history(server):
+    """command.dispatch /retry with empty history returns error."""
+    sid = "test-session"
+    server._sessions[sid] = {
+        "session_key": sid,
+        "agent": None,
+        "history": [],
+        "history_lock": threading.Lock(),
+        "history_version": 0,
+    }
+
+    resp = server.handle_request({
+        "id": "r5",
+        "method": "command.dispatch",
+        "params": {"name": "retry", "session_id": sid},
+    })
+
+    assert "error" in resp
+    assert resp["error"]["code"] == 4018
+
+
+def test_command_dispatch_retry_handles_multipart_content(server):
+    """command.dispatch /retry extracts text from multipart content lists."""
+    sid = "test-session"
+    history = [
+        {"role": "user", "content": [
+            {"type": "text", "text": "analyze this"},
+            {"type": "image_url", "image_url": {"url": "data:image/png;base64,..."}}
+        ]},
+        {"role": "assistant", "content": "I see the image."},
+    ]
+    server._sessions[sid] = {
+        "session_key": sid,
+        "agent": None,
+        "history": history,
+        "history_lock": threading.Lock(),
+        "history_version": 0,
+    }
+
+    resp = server.handle_request({
+        "id": "r6",
+        "method": "command.dispatch",
+        "params": {"name": "retry", "session_id": sid},
+    })
+
+    assert "error" not in resp
+    result = resp["result"]
+    assert result["type"] == "send"
+    assert result["message"] == "analyze this"
+
+
 def test_command_dispatch_returns_skill_payload(server):
     """command.dispatch returns structured skill payload for the TUI to send()."""
     sid = "test-session"
diff --git a/tui_gateway/server.py b/tui_gateway/server.py
index bf8425a8d..ccb9f7260 100644
--- a/tui_gateway/server.py
+++ b/tui_gateway/server.py
@@ -1949,6 +1949,13 @@ _TUI_EXTRA: list[tuple[str, str, str]] = [
     ("/logs", "Show recent gateway log lines", "TUI"),
 ]
 
+# Commands that queue messages onto _pending_input in the CLI.
+# In the TUI the slash worker subprocess has no reader for that queue,
+# so slash.exec rejects them → TUI falls through to command.dispatch.
+_PENDING_INPUT_COMMANDS: frozenset[str] = frozenset({
+    "retry", "queue", "q", "steer", "plan",
+})
+
 
 @method("commands.catalog")
 def _(rid, params: dict) -> dict:
@@ -2127,20 +2134,32 @@ def _(rid, params: dict) -> dict:
         return _ok(rid, {"type": "send", "message": arg})
 
     if name == "retry":
-        agent = session.get("agent") if session else None
-        if agent and hasattr(agent, "conversation_history"):
-            hist = agent.conversation_history or []
-            for m in reversed(hist):
-                if m.get("role") == "user":
-                    content = m.get("content", "")
-                    if isinstance(content, list):
-                        content = " ".join(
-                            p.get("text", "") for p in content if isinstance(p, dict) and p.get("type") == "text"
-                        )
-                    if content:
-                        return _ok(rid, {"type": "send", "message": content})
+        if not session:
+            return _err(rid, 4001, "no active session to retry")
+        history = session.get("history", [])
+        if not history:
             return _err(rid, 4018, "no previous user message to retry")
-        return _err(rid, 4018, "no active session to retry")
+        # Walk backwards to find the last user message
+        last_user_idx = None
+        for i in range(len(history) - 1, -1, -1):
+            if history[i].get("role") == "user":
+                last_user_idx = i
+                break
+        if last_user_idx is None:
+            return _err(rid, 4018, "no previous user message to retry")
+        content = history[last_user_idx].get("content", "")
+        if isinstance(content, list):
+            content = " ".join(
+                p.get("text", "") for p in content if isinstance(p, dict) and p.get("type") == "text"
+            )
+        if not content:
+            return _err(rid, 4018, "last user message is empty")
+        # Truncate history: remove everything from the last user message onward
+        # (mirrors CLI retry_last() which strips the failed exchange)
+        with session["history_lock"]:
+            session["history"] = history[:last_user_idx]
+            session["history_version"] = int(session.get("history_version", 0)) + 1
+        return _ok(rid, {"type": "send", "message": content})
 
     if name == "steer":
         if not arg:
@@ -2159,9 +2178,16 @@ def _(rid, params: dict) -> dict:
     if name == "plan":
         try:
             from agent.skill_commands import build_skill_invocation_message as _bsim, build_plan_path
-            plan_path = build_plan_path(session.get("session_key", "") if session else "")
-            msg = _bsim("/plan", f"{arg} {plan_path}".strip() if arg else plan_path,
-                        task_id=session.get("session_key", "") if session else "")
+            user_instruction = arg or ""
+            plan_path = build_plan_path(user_instruction)
+            msg = _bsim(
+                "/plan", user_instruction,
+                task_id=session.get("session_key", "") if session else "",
+                runtime_note=(
+                    "Save the markdown plan with write_file to this exact relative path "
+                    f"inside the active workspace/backend cwd: {plan_path}"
+                ),
+            )
             if msg:
                 return _ok(rid, {"type": "send", "message": msg})
         except Exception as e:
@@ -2383,19 +2409,12 @@ def _(rid, params: dict) -> dict:
     if not cmd:
         return _err(rid, 4004, "empty command")
 
-    # Skill slash commands (e.g. /hermes-agent-dev) must NOT go through the
-    # slash worker — process_command() queues the skill payload onto
-    # _pending_input which nobody reads in the worker subprocess.  Reject
-    # here so the TUI falls through to command.dispatch which handles skills
-    # correctly (builds the invocation message and returns it to the client).
-    #
-    # The same applies to /retry, /queue, /steer, and /plan — they all
-    # put messages on _pending_input that the slash worker never reads.
+    # Skill slash commands and _pending_input commands must NOT go through the
+    # slash worker — see _PENDING_INPUT_COMMANDS definition above.
     # (/browser connect/disconnect also uses _pending_input for context
     # notes, but the actual browser operations need the slash worker's
     # env-var side effects, so they stay in slash.exec — only the context
     # note to the model is lost, which is low-severity.)
-    _PENDING_INPUT_COMMANDS = frozenset({"retry", "queue", "q", "steer", "plan"})
     _cmd_parts = cmd.split() if not cmd.startswith("/") else cmd.lstrip("/").split()
     _cmd_base = _cmd_parts[0] if _cmd_parts else ""
 
@@ -2403,9 +2422,9 @@ def _(rid, params: dict) -> dict:
         return _err(rid, 4018, f"pending-input command: use command.dispatch for /{_cmd_base}")
 
     try:
-        from agent.skill_commands import scan_skill_commands
+        from agent.skill_commands import get_skill_commands
         _cmd_key = f"/{_cmd_base}"
-        if _cmd_key in scan_skill_commands():
+        if _cmd_key in get_skill_commands():
             return _err(rid, 4018, f"skill command: use command.dispatch for {_cmd_key}")
     except Exception:
         pass
diff --git a/ui-tui/src/components/messageLine.tsx b/ui-tui/src/components/messageLine.tsx
index 9cf78c159..9de6f2aa1 100644
--- a/ui-tui/src/components/messageLine.tsx
+++ b/ui-tui/src/components/messageLine.tsx
@@ -28,13 +28,14 @@ export const MessageLine = memo(function MessageLine({
   }
 
   if (msg.role === 'tool') {
-    const preview = compactPreview(hasAnsi(msg.text) ? stripAnsi(msg.text) : msg.text, Math.max(24, cols - 14)) ||
-      '(empty tool result)'
+    const maxChars = Math.max(24, cols - 14)
+    const stripped = hasAnsi(msg.text) ? stripAnsi(msg.text) : msg.text
+    const preview = compactPreview(stripped, maxChars) || '(empty tool result)'
 
     return (
       <Box alignSelf="flex-start" borderColor={t.color.dim} borderStyle="round" marginLeft={3} paddingX={1}>
         {hasAnsi(msg.text) ? (
-          <Ansi>{compactPreview(msg.text, Math.max(24, cols - 14)) || '(empty tool result)'}</Ansi>
+          <Text wrap="truncate-end"><Ansi>{msg.text}</Ansi></Text>
         ) : (
           <Text color={t.color.dim} wrap="truncate-end">
             {preview}