diff --git a/Cargo.lock b/Cargo.lock
index d4129a33e..972f4e882 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -1510,9 +1510,9 @@ dependencies = [
 
 [[package]]
 name = "convert_case"
-version = "0.8.0"
+version = "0.10.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "baaaa0ecca5b51987b9423ccdc971514dd8b0bb7b4060b983d3664dad3f1f89f"
+checksum = "633458d4ef8c78b72454de2d54fd6ab2e60f9e02be22f3c6104cdc8a4e0fceb9"
 dependencies = [
  "unicode-segmentation",
 ]
@@ -7351,9 +7351,9 @@ dependencies = [
 
 [[package]]
 name = "rig-core"
-version = "0.31.0"
+version = "0.33.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "437fa2a15825caf2505411bbe55b05c8eb122e03934938b38f9ecaa1d6ded7c8"
+checksum = "a529b9b72f51a46a9ea87c9ba8031e36593de7a89461983f01d8c24462f9eb06"
 dependencies = [
  "as-any",
  "async-stream",
@@ -7377,6 +7377,7 @@ dependencies = [
  "serde_json",
  "thiserror 2.0.18",
  "tokio",
+ "tokio-tungstenite 0.23.1",
  "tracing",
  "tracing-futures",
  "url",
@@ -7384,11 +7385,11 @@ dependencies = [
 
 [[package]]
 name = "rig-derive"
-version = "0.1.10"
+version = "0.1.11"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b1f4b48f1449fa214d5cb11d0d0d952fd4c13b7ca5d1eaac64c87ce03cfb9e24"
+checksum = "3b6d9818c9cb13d00664b52fd3e47b0554bc2d5c59cfb90340dd9411b09553bc"
 dependencies = [
- "convert_case 0.8.0",
+ "convert_case 0.10.0",
  "deluxe",
  "indoc",
  "proc-macro2",
@@ -9469,6 +9470,22 @@ dependencies = [
  "webpki-roots 0.26.11",
 ]
 
+[[package]]
+name = "tokio-tungstenite"
+version = "0.23.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "c6989540ced10490aaf14e6bad2e3d33728a2813310a0c71d1574304c49631cd"
+dependencies = [
+ "futures-util",
+ "log",
+ "rustls 0.23.36",
+ "rustls-pki-types",
+ "tokio",
+ "tokio-rustls 0.26.4",
+ "tungstenite 0.23.0",
+ "webpki-roots 0.26.11",
+]
+
 [[package]]
 name = "tokio-tungstenite"
 version = "0.28.0"
@@ -9823,6 +9840,26 @@ dependencies = [
  "utf-8",
 ]
 
+[[package]]
+name = "tungstenite"
+version = "0.23.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "6e2e2ce1e47ed2994fd43b04c8f618008d4cabdd5ee34027cf14f9d918edd9c8"
+dependencies = [
+ "byteorder",
+ "bytes",
+ "data-encoding",
+ "http 1.4.0",
+ "httparse",
+ "log",
+ "rand 0.8.5",
+ "rustls 0.23.36",
+ "rustls-pki-types",
+ "sha1",
+ "thiserror 1.0.69",
+ "utf-8",
+]
+
 [[package]]
 name = "tungstenite"
 version = "0.28.0"
diff --git a/Cargo.toml b/Cargo.toml
index eb157b1c9..f04c84646 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -17,7 +17,7 @@ serde = { version = "1.0", features = ["derive"] }
 serde_json = "1.0"
 
 # LLM / Rig framework
-rig = { version = "0.31", package = "rig-core", features = ["derive"] }
+rig = { version = "0.33", package = "rig-core", features = ["derive"] }
 
 # HTTP clients for LLM providers
 reqwest = { version = "0.13", features = ["json", "stream", "form", "query", "gzip"] }
diff --git a/src/agent/compactor.rs b/src/agent/compactor.rs
index ea2856b45..5f7efc4b7 100644
--- a/src/agent/compactor.rs
+++ b/src/agent/compactor.rs
@@ -284,6 +284,9 @@ pub fn estimate_history_tokens(history: &[Message]) -> usize {
                     chars += estimate_assistant_content_chars(item);
                 }
             }
+            Message::System { content } => {
+                chars += content.len();
+            }
         }
     }
 
@@ -381,6 +384,11 @@ fn render_messages_as_transcript(messages: &[Message]) -> String {
                     }
                 }
             }
+            Message::System { content } => {
+                output.push_str("System: ");
+                output.push_str(content);
+                output.push('\n');
+            }
         }
     }
 
diff --git a/src/agent/worker.rs b/src/agent/worker.rs
index bfaf89170..58c21d8e3 100644
--- a/src/agent/worker.rs
+++ b/src/agent/worker.rs
@@ -938,6 +938,10 @@ impl Worker {
                         }
                     }
                 }
+                rig::message::Message::System { content } => {
+                    let _ = writeln!(log, "[{index}] System:");
+                    let _ = writeln!(log, "  {content}");
+                }
             }
         }
 
@@ -1130,6 +1134,7 @@ fn build_worker_recap(messages: &[rig::message::Message]) -> String {
                     }
                 }
             }
+            rig::message::Message::System { .. } => {}
         }
     }
 
diff --git a/src/conversation/worker_transcript.rs b/src/conversation/worker_transcript.rs
index 09d6aa9f9..23ec340f2 100644
--- a/src/conversation/worker_transcript.rs
+++ b/src/conversation/worker_transcript.rs
@@ -26,6 +26,11 @@ pub enum TranscriptStep {
     /// the correct `Message::User` role instead of treating everything as
     /// `Message::Assistant`.
     UserText { text: String },
+    /// System-originated text (preamble, system prompt).
+    ///
+    /// Distinct from `UserText` so that system messages preserve their role
+    /// when round-tripped through the transcript.
+    SystemText { text: String },
     /// Tool execution result.
     ToolResult {
         call_id: String,
@@ -363,6 +368,13 @@ pub fn transcript_to_history(steps: &[TranscriptStep]) -> Vec<rig::message::Mess
                     });
                 }
             }
+            TranscriptStep::SystemText { text } => {
+                if !text.is_empty() {
+                    messages.push(Message::System {
+                        content: text.clone(),
+                    });
+                }
+            }
             TranscriptStep::ToolResult {
                 call_id,
                 name: _,
@@ -462,6 +474,11 @@ fn convert_history(history: &[rig::message::Message]) -> Vec<TranscriptStep> {
                     }
                 }
             }
+            rig::message::Message::System { content } => {
+                steps.push(TranscriptStep::SystemText {
+                    text: content.clone(),
+                });
+            }
         }
     }
 
diff --git a/src/llm/model.rs b/src/llm/model.rs
index a40a1d313..ddaef3cd2 100644
--- a/src/llm/model.rs
+++ b/src/llm/model.rs
@@ -1306,6 +1306,10 @@ pub fn convert_messages_to_anthropic(messages: &OneOrMany<Message>) -> Vec<serde
                 (!parts.is_empty())
                     .then(|| serde_json::json!({"role": "assistant", "content": parts}))
             }
+            Message::System { content } => Some(serde_json::json!({
+                "role": "user",
+                "content": content,
+            })),
         })
         .collect()
 }
@@ -1367,6 +1371,12 @@ fn convert_messages_to_openai(messages: &OneOrMany<Message>) -> Vec<serde_json::
 
                 result.extend(tool_results);
             }
+            Message::System { content } => {
+                result.push(serde_json::json!({
+                    "role": "user",
+                    "content": content,
+                }));
+            }
             Message::Assistant { content, .. } => {
                 let mut text_parts = Vec::new();
                 let mut reasoning_parts = Vec::new();
@@ -1486,6 +1496,12 @@ fn convert_messages_to_openai_responses(messages: &OneOrMany<Message>) -> Vec<se
                     }));
                 }
             }
+            Message::System { content } => {
+                result.push(serde_json::json!({
+                    "role": "user",
+                    "content": content,
+                }));
+            }
             Message::Assistant { content, .. } => {
                 let mut text_parts = Vec::new();
                 let mut reasoning_parts = Vec::new();
@@ -3068,6 +3084,39 @@ mod tests {
         assert!(error.to_string().contains("stop_reason: max_tokens"));
     }
 
+    #[test]
+    fn convert_messages_to_anthropic_maps_system_to_user_role() {
+        let messages = OneOrMany::one(Message::System {
+            content: "You are a helpful assistant".to_string(),
+        });
+        let converted = convert_messages_to_anthropic(&messages);
+        assert_eq!(converted.len(), 1);
+        assert_eq!(converted[0]["role"], "user");
+        assert_eq!(converted[0]["content"], "You are a helpful assistant");
+    }
+
+    #[test]
+    fn convert_messages_to_openai_maps_system_to_user_role() {
+        let messages = OneOrMany::one(Message::System {
+            content: "You are a helpful assistant".to_string(),
+        });
+        let converted = convert_messages_to_openai(&messages);
+        assert_eq!(converted.len(), 1);
+        assert_eq!(converted[0]["role"], "user");
+        assert_eq!(converted[0]["content"], "You are a helpful assistant");
+    }
+
+    #[test]
+    fn convert_messages_to_openai_responses_maps_system_to_user_role() {
+        let messages = OneOrMany::one(Message::System {
+            content: "You are a helpful assistant".to_string(),
+        });
+        let converted = convert_messages_to_openai_responses(&messages);
+        assert_eq!(converted.len(), 1);
+        assert_eq!(converted[0]["role"], "user");
+        assert_eq!(converted[0]["content"], "You are a helpful assistant");
+    }
+
     #[test]
     fn parse_openai_response_handles_content_array_parts() {
         let body = serde_json::json!({
diff --git a/src/tools/worker_inspect.rs b/src/tools/worker_inspect.rs
index edac9db8e..428bf26e5 100644
--- a/src/tools/worker_inspect.rs
+++ b/src/tools/worker_inspect.rs
@@ -135,6 +135,9 @@ impl Tool for WorkerInspectTool {
                             worker_transcript::TranscriptStep::UserText { text } => {
                                 summary.push_str(&format!("**User:** {text}\n\n"));
                             }
+                            worker_transcript::TranscriptStep::SystemText { text } => {
+                                summary.push_str(&format!("**System:** {text}\n\n"));
+                            }
                             worker_transcript::TranscriptStep::ToolResult {
                                 name, text, ..
                             } => {