Format prompt guidance assertions

Co-authored-by: Copilot <[email protected]>

src/extensions/mod.rs

@@ -2,7 +2,8 @@
 //! and activation of channels, tools, and MCP servers.
 //!
 //! Extensions are the user-facing abstraction that unifies three runtime kinds:
-//! - **Channels** (Telegram, Slack, Discord) — messaging integrations (WASM)
+//! - **Channels** (Telegram, Slack, Discord) — messaging platform connections
+//!   and conversation transports (WASM)
 //! - **Tools** — sandboxed capabilities (WASM)
 //! - **MCP servers** — external API integrations via Model Context Protocol
 //!

src/llm/reasoning.rs

@@ -1017,8 +1017,11 @@ Example:
 
         "\n\n## Extensions\n\
          You can search, install, and activate extensions to add new capabilities:\n\
-         - **Channels** (Telegram, Slack, Discord) — messaging integrations. \
-         When users ask about connecting a messaging platform, search for it as a channel.\n\
+         - **Channels** (Telegram, Slack, Discord) — connect messaging platforms so users can \
+         talk to you there. When users ask about connecting a messaging platform, search for it \
+         as a channel. Channels are not separate send-message tools; use normal assistant output \
+         to reply in the current conversation, and use the `message` tool only for proactive, \
+         background, or cross-channel outbound sends.\n\
          - **Tools** — sandboxed functions that extend your abilities.\n\
          - **MCP servers** — external API integrations via the Model Context Protocol.\n\n\
          Use `tool_search` to find extensions by name. Refer to them by their kind \
@@ -1059,15 +1062,20 @@ Example:
 
         let message_tool_hint = "\
 \n\n## Proactive Messaging\n\
+For ordinary replies in the current conversation, respond normally without calling `message`.\n\
 Send messages via Signal, Telegram, Slack, or other connected channels:\n\
 - `content` (required): the message text\n\
 - `attachments` (optional): array of file paths to send\n\
 - `channel` (optional): which channel to use (signal, telegram, slack, etc.)\n\
 - `target` (optional): who to send to (phone number, group ID, etc.)\n\
-\nOmit both `channel` and `target` to send to the current conversation.\n\
+\nOmit both `channel` and `target` for a proactive follow-up in the current conversation.\n\
+Target formats:\n\
+- Signal: E.164 phone number (`+1234567890`) or group ID\n\
+- Telegram: username or chat ID\n\
+- Slack: channel name (`#general`) or user ID\n\
 Examples (tool calls use JSON format):\n\
-- Reply here: {\"content\": \"Hi!\"}\n\
-- Send file here: {\"content\": \"Here's the file\", \"attachments\": [\"/path/to/file.txt\"]}\n\
+- Proactive follow-up here: {\"content\": \"Hi again!\"}\n\
+- Send file here proactively: {\"content\": \"Here's the file\", \"attachments\": [\"/path/to/file.txt\"]}\n\
 - Message a different user: {\"channel\": \"signal\", \"target\": \"+1234567890\", \"content\": \"Hi!\"}\n\
 - Message a different group: {\"channel\": \"signal\", \"target\": \"group:abc123\", \"content\": \"Hi!\"}";
 
@@ -1105,7 +1113,9 @@ Examples (tool calls use JSON format):\n\
 
         format!(
             "\n\n## Current Conversation\n\
-             This is who you're talking to (omit 'target' to send here):\n{}",
+             This is who you're talking to in the active conversation. Use normal assistant \
+             output to reply here; only use the `message` tool for proactive, background, or \
+             cross-channel outbound sends:\n{}",
             lines.join("\n")
         )
     }
@@ -2452,6 +2462,54 @@ That's my plan."#;
         );
     }
 
+    #[test]
+    fn test_extensions_section_clarifies_channels_are_not_send_tools() {
+        let reasoning = make_test_reasoning();
+        let tool_defs = vec![ToolDefinition {
+            name: "tool_search".to_string(),
+            description: "Search extensions".to_string(),
+            parameters: serde_json::json!({}),
+        }];
+
+        let section = reasoning.build_extensions_section_for_tools(&tool_defs);
+        assert!(section.contains("connect messaging platforms so users can talk to you there"));
+        assert!(section.contains("Channels are not separate send-message tools"));
+        assert!(
+            section.contains("use normal assistant output to reply in the current conversation")
+        );
+        assert!(section.contains(
+            "`message` tool only for proactive, background, or cross-channel outbound sends"
+        ));
+    }
+
+    #[test]
+    fn test_channel_section_separates_normal_replies_from_message_tool() {
+        let reasoning = make_test_reasoning().with_channel("telegram");
+
+        let section = reasoning.build_channel_section();
+        assert!(section.contains("respond normally without calling `message`"));
+        assert!(section.contains("proactive follow-up in the current conversation"));
+        assert!(section.contains("Target formats:"));
+        assert!(section.contains("Signal: E.164 phone number"));
+        assert!(section.contains("Telegram: username or chat ID"));
+        assert!(section.contains("Slack: channel name"));
+        assert!(section.contains("Proactive follow-up here"));
+    }
+
+    #[test]
+    fn test_current_conversation_section_does_not_imply_message_tool_for_replies() {
+        let reasoning = make_test_reasoning()
+            .with_channel("telegram")
+            .with_conversation_data("User", "telegram-user");
+
+        let section = reasoning.build_conversation_section();
+        assert!(section.contains("Use normal assistant output to reply here"));
+        assert!(section.contains(
+            "only use the `message` tool for proactive, background, or cross-channel outbound sends"
+        ));
+        assert!(!section.contains("omit 'target' to send here"));
+    }
+
     // ---- plan/evaluate bypass clean_response (Bug #564-2) ----
 
     #[test]

src/tools/builtin/extension_tools.rs

@@ -31,8 +31,11 @@ impl Tool for ToolSearchTool {
 
     fn description(&self) -> &str {
         "Search for available extensions to add new capabilities. Extensions include \
-         channels (Telegram, Slack, Discord — for messaging), tools, and MCP servers. \
-         Use discover:true to search online if the built-in registry has no results."
+         channels (Telegram, Slack, Discord — connect messaging platforms so IronClaw can \
+         receive and reply there), tools, and MCP servers. Use `tool_install` and \
+         `tool_activate` to install and enable channels; use the `message` tool for proactive \
+         outbound sends. Use discover:true to search online if the built-in registry has no \
+         results."
     }
 
     fn parameters_schema(&self) -> serde_json::Value {
@@ -634,6 +637,17 @@ mod tests {
         assert!(schema["properties"].get("query").is_some());
     }
 
+    #[test]
+    fn test_tool_search_description_clarifies_channel_setup_vs_sending() {
+        let tool = ToolSearchTool {
+            manager: test_manager_stub(),
+        };
+
+        let description = tool.description();
+        assert!(description.contains("Use `tool_install` and `tool_activate`"));
+        assert!(description.contains("use the `message` tool for proactive outbound sends"));
+    }
+
     #[test]
     fn test_tool_install_schema() {
         use crate::tools::tool::ApprovalRequirement;

src/tools/builtin/message.rs

@@ -181,11 +181,15 @@ impl Tool for MessageTool {
     }
 
     fn description(&self) -> &str {
-        "Send a message to a channel. If channel/target omitted, uses the current conversation's \
-         channel and sender/group. Use to proactively message users on any connected channel. \
+        "Send a proactive message to a channel. Use normal assistant output to reply in the \
+         active conversation; use this tool for proactive notifications, routine/background \
+         follow-ups, attachments, or sending to a different channel/recipient. If channel/target \
+         are omitted, reuses the current conversation's channel and sender/group when available. \
+         If you provide `target` without `channel` and no scoped channel can be resolved, the \
+         message may be broadcast across connected channels instead of sent to just one. \
          Supports file attachments: first download the file with the http tool using save_to \
-         (e.g., http GET https://picsum.photos/800/600 save_to=/tmp/photo.jpg), then pass \
-         the file path in the attachments array. Images are sent as photos on Telegram. \
+         (e.g., http GET https://picsum.photos/800/600 save_to=/tmp/photo.jpg), then pass the \
+         file path in the attachments array. Images are sent as photos on Telegram. \
          - Signal: target accepts E.164 (+1234567890) or group ID \
          - Telegram: target accepts username or chat ID \
          - Slack: target accepts channel (#general) or user ID"
@@ -451,7 +455,11 @@ mod tests {
     #[test]
     fn message_tool_description() {
         let tool = MessageTool::new(Arc::new(ChannelManager::new()));
-        assert!(!tool.description().is_empty());
+        let description = tool.description();
+        assert!(!description.is_empty());
+        assert!(description.contains("Use normal assistant output to reply"));
+        assert!(description.contains("proactive notifications"));
+        assert!(description.contains("provide `target` without `channel`"));
     }
 
     #[test]

tests/e2e_builtin_tool_coverage.rs

@@ -13,7 +13,7 @@ mod tests {
     use ironclaw::agent::routine::{RoutineAction, Trigger};
 
     use crate::support::test_rig::TestRigBuilder;
-    use crate::support::trace_llm::LlmTrace;
+    use crate::support::trace_llm::{LlmTrace, TraceResponse, TraceStep, TraceToolCall, TraceTurn};
 
     // -----------------------------------------------------------------------
     // Test 1: time_parse_and_diff
@@ -838,4 +838,112 @@ mod tests {
 
         rig.shutdown();
     }
+
+    #[tokio::test]
+    async fn tool_info_clarifies_message_and_channel_setup_roles() {
+        let trace = LlmTrace::new(
+            "test-tool-info-channel-message-clarity",
+            vec![TraceTurn {
+                user_input: "How do message and channels differ?".to_string(),
+                steps: vec![
+                    TraceStep {
+                        request_hint: None,
+                        response: TraceResponse::ToolCalls {
+                            tool_calls: vec![TraceToolCall {
+                                id: "call_tool_info_message".to_string(),
+                                name: "tool_info".to_string(),
+                                arguments: serde_json::json!({"name": "message"}),
+                            }],
+                            input_tokens: 100,
+                            output_tokens: 20,
+                        },
+                        expected_tool_results: Vec::new(),
+                    },
+                    TraceStep {
+                        request_hint: None,
+                        response: TraceResponse::ToolCalls {
+                            tool_calls: vec![TraceToolCall {
+                                id: "call_tool_info_tool_search".to_string(),
+                                name: "tool_info".to_string(),
+                                arguments: serde_json::json!({"name": "tool_search"}),
+                            }],
+                            input_tokens: 140,
+                            output_tokens: 20,
+                        },
+                        expected_tool_results: Vec::new(),
+                    },
+                    TraceStep {
+                        request_hint: None,
+                        response: TraceResponse::Text {
+                            content: "I checked both tool descriptions.".to_string(),
+                            input_tokens: 220,
+                            output_tokens: 30,
+                        },
+                        expected_tool_results: Vec::new(),
+                    },
+                ],
+                expects: Default::default(),
+            }],
+        );
+
+        let rig = TestRigBuilder::new()
+            .with_trace(trace.clone())
+            .with_auto_approve_tools(true)
+            .build()
+            .await;
+
+        rig.send_message("How do message and channels differ?")
+            .await;
+        let responses = rig.wait_for_responses(1, Duration::from_secs(15)).await;
+
+        rig.verify_trace_expects(&trace, &responses);
+
+        let results = rig.tool_results();
+        let info_results: Vec<_> = results.iter().filter(|(n, _)| n == "tool_info").collect();
+        assert_eq!(info_results.len(), 2, "Expected two tool_info results");
+
+        let info_json: Vec<serde_json::Value> = info_results
+            .iter()
+            .map(|(_, preview)| {
+                serde_json::from_str(preview)
+                    .expect("tool_info result preview should be valid JSON")
+            })
+            .collect();
+
+        let message_json = info_json
+            .iter()
+            .find(|info| info["name"] == "message")
+            .expect("tool_info result should contain 'message'");
+        let message_description = message_json["description"]
+            .as_str()
+            .expect("message description should be a string");
+        assert!(
+            message_description.contains("Use normal assistant output to reply"),
+            "message description should distinguish normal replies: {message_description}"
+        );
+        assert!(
+            message_description.contains("proactive notifications"),
+            "message description should describe proactive sends: {message_description}"
+        );
+
+        let tool_search_json = info_json
+            .iter()
+            .find(|info| info["name"] == "tool_search")
+            .expect("tool_info result should contain 'tool_search'");
+        let tool_search_description = tool_search_json["description"]
+            .as_str()
+            .expect("tool_search description should be a string");
+        assert!(
+            tool_search_description.contains("`tool_install`")
+                && tool_search_description.contains("`tool_activate`"),
+            "tool_search description should describe setup/activation via tool_install and \
+             tool_activate: {tool_search_description}"
+        );
+        assert!(
+            tool_search_description.contains("use the `message` tool for proactive outbound sends"),
+            "tool_search description should point outbound sends to message: {tool_search_description}"
+        );
+
+        rig.shutdown();
+    }
 }

tests/multi_tenant_system_prompt.rs

@@ -237,4 +237,47 @@ mod tests {
 
         rig.shutdown();
     }
+
+    #[tokio::test]
+    async fn telegram_system_prompt_clarifies_reply_vs_proactive_message_tool() {
+        let trace = simple_trace(1);
+        let rig = TestRigBuilder::new().with_trace(trace).build().await;
+
+        let msg = IncomingMessage::new("telegram", "telegram-user", "Hello there");
+        rig.send_incoming(msg).await;
+        let _responses = rig.wait_for_responses(1, TIMEOUT).await;
+
+        let requests = rig.captured_llm_requests();
+        let system_prompt =
+            extract_system_prompt(&requests).expect("Expected a system prompt in the LLM request");
+
+        assert!(
+            system_prompt.contains("Channels are not separate send-message tools"),
+            "System prompt should describe channels as setup/integration surfaces.\n\
+             Actual system prompt:\n{system_prompt}"
+        );
+        assert!(
+            system_prompt
+                .contains("use normal assistant output to reply in the current conversation"),
+            "System prompt should route ordinary replies through normal assistant output.\n\
+             Actual system prompt:\n{system_prompt}"
+        );
+        assert!(
+            system_prompt.contains("respond normally without calling `message`"),
+            "System prompt should say normal replies do not use the message tool.\n\
+             Actual system prompt:\n{system_prompt}"
+        );
+        assert!(
+            system_prompt.contains("proactive follow-up in the current conversation"),
+            "System prompt should reserve omitted channel/target for proactive follow-ups.\n\
+             Actual system prompt:\n{system_prompt}"
+        );
+        assert!(
+            !system_prompt.contains("omit 'target' to send here"),
+            "System prompt should not imply the message tool is the default way to reply \
+             in-thread.\nActual system prompt:\n{system_prompt}"
+        );
+
+        rig.shutdown();
+    }
 }