diff --git a/rust/crates/runtime/src/conversation.rs b/rust/crates/runtime/src/conversation.rs
index 1dde559..c29f834 100644
--- a/rust/crates/runtime/src/conversation.rs
+++ b/rust/crates/runtime/src/conversation.rs
@@ -292,6 +292,24 @@ where
         }
     }
 
+    /// Run a session health probe to verify the runtime is functional after compaction.
+    /// Returns Ok(()) if healthy, Err if the session appears broken.
+    fn run_session_health_probe(&mut self) -> Result<(), String> {
+        // Check if we have basic session integrity
+        if self.session.messages.is_empty() && self.session.compaction.is_some() {
+            // Freshly compacted with no messages - this is normal
+            return Ok(());
+        }
+
+        // Verify tool executor is responsive with a non-destructive probe
+        // Using glob_search with a pattern that won't match anything
+        let probe_input = r#"{"pattern": "*.health-check-probe-"}"#;
+        match self.tool_executor.execute("glob_search", probe_input) {
+            Ok(_) => Ok(()),
+            Err(e) => Err(format!("Tool executor probe failed: {e}")),
+        }
+    }
+
     #[allow(clippy::too_many_lines)]
     pub fn run_turn(
         &mut self,
@@ -299,6 +317,18 @@ where
         mut prompter: Option<&mut dyn PermissionPrompter>,
     ) -> Result<TurnSummary, RuntimeError> {
         let user_input = user_input.into();
+
+        // ROADMAP #38: Session-health canary - probe if context was compacted
+        if self.session.compaction.is_some() {
+            if let Err(error) = self.run_session_health_probe() {
+                return Err(RuntimeError::new(format!(
+                    "Session health probe failed after compaction: {error}. \
+                     The session may be in an inconsistent state. \
+                     Consider starting a fresh session with /session new."
+                )));
+            }
+        }
+
         self.record_turn_started(&user_input);
         self.session
             .push_user_text(user_input)
diff --git a/rust/crates/runtime/src/session.rs b/rust/crates/runtime/src/session.rs
index 0a0a61a..7d905fa 100644
--- a/rust/crates/runtime/src/session.rs
+++ b/rust/crates/runtime/src/session.rs
@@ -98,6 +98,8 @@ pub struct Session {
     pub prompt_history: Vec<SessionPromptEntry>,
     /// The model used in this session, persisted so resumed sessions can
     /// report which model was originally used.
+    /// Timestamp of last successful health check (ROADMAP #38)
+    pub last_health_check_ms: Option<u64>,
     pub model: Option<String>,
     persistence: Option<SessionPersistence>,
 }
@@ -113,6 +115,7 @@ impl PartialEq for Session {
             && self.fork == other.fork
             && self.workspace_root == other.workspace_root
             && self.prompt_history == other.prompt_history
+            && self.last_health_check_ms == other.last_health_check_ms
     }
 }
 
@@ -164,6 +167,7 @@ impl Session {
             fork: None,
             workspace_root: None,
             prompt_history: Vec::new(),
+            last_health_check_ms: None,
             model: None,
             persistence: None,
         }
@@ -267,6 +271,7 @@ impl Session {
             }),
             workspace_root: self.workspace_root.clone(),
             prompt_history: self.prompt_history.clone(),
+            last_health_check_ms: self.last_health_check_ms,
             model: self.model.clone(),
             persistence: None,
         }
@@ -390,6 +395,7 @@ impl Session {
             fork,
             workspace_root,
             prompt_history,
+            last_health_check_ms: None,
             model,
             persistence: None,
         })
@@ -490,6 +496,7 @@ impl Session {
             fork,
             workspace_root,
             prompt_history,
+            last_health_check_ms: None,
             model,
             persistence: None,
         })