diff --git a/crates/wick/wick-host/Cargo.toml b/crates/wick/wick-host/Cargo.toml
index ed0f9ccc..56054af6 100644
--- a/crates/wick/wick-host/Cargo.toml
+++ b/crates/wick/wick-host/Cargo.toml
@@ -33,6 +33,7 @@ futures = { workspace = true }
 derive_builder = { workspace = true }
 option-utils = { workspace = true }
 async-trait = { workspace = true }
+structured-output = { workspace = true }
 
 
 [dev-dependencies]
diff --git a/crates/wick/wick-host/src/app_host.rs b/crates/wick/wick-host/src/app_host.rs
index 9e458c9a..1b750f96 100644
--- a/crates/wick/wick-host/src/app_host.rs
+++ b/crates/wick/wick-host/src/app_host.rs
@@ -3,6 +3,7 @@ use std::sync::Arc;
 
 use futures::future::{join_all, select};
 use futures::pin_mut;
+use structured_output::StructuredOutput;
 use tokio::task::{JoinError, JoinHandle};
 use tracing::Span;
 use wick_config::config::AppConfiguration;
@@ -129,7 +130,7 @@ impl AppHost {
   }
 
   #[allow(clippy::unused_async)]
-  pub async fn wait_for_done(&mut self) -> Result<()> {
+  pub async fn wait_for_done(&mut self) -> Result<Vec<StructuredOutput>> {
     let state = self.triggers.take().unwrap();
     let (triggers, start_tasks): (Vec<_>, Vec<_>) = state
       .triggers
@@ -138,6 +139,7 @@ impl AppHost {
       .unzip();
     join_all(start_tasks).await;
     self.span.in_scope(|| debug!("all triggers started"));
+    let mut all_output = Vec::new();
     for trigger in &triggers {
       let ctrl_c = async {
         let _ = tokio::signal::ctrl_c().await;
@@ -148,14 +150,15 @@ impl AppHost {
           self.span.in_scope(|| debug!("ctrl-c received, stopping triggers"));
           break;
         }
-        futures::future::Either::Right(_) => {
+        futures::future::Either::Right((output, _)) => {
           self.span.in_scope(|| debug!("trigger finished"));
+          all_output.push(output);
         }
       }
     }
     self.span.in_scope(|| debug!("all triggers finished"));
 
-    Ok(())
+    Ok(all_output)
   }
 }
 
diff --git a/crates/wick/wick-runtime/src/triggers/cli.rs b/crates/wick/wick-runtime/src/triggers/cli.rs
index b9851c2f..b5c84a67 100644
--- a/crates/wick/wick-runtime/src/triggers/cli.rs
+++ b/crates/wick/wick-runtime/src/triggers/cli.rs
@@ -19,8 +19,8 @@ use crate::Runtime;
 
 #[derive(Debug)]
 pub(crate) struct Cli {
-  done_tx: Mutex<Option<tokio::sync::oneshot::Sender<()>>>,
-  done_rx: Mutex<Option<tokio::sync::oneshot::Receiver<()>>>,
+  done_tx: Mutex<Option<tokio::sync::oneshot::Sender<StructuredOutput>>>,
+  done_rx: Mutex<Option<tokio::sync::oneshot::Receiver<StructuredOutput>>>,
 }
 
 #[derive(Debug, PartialEq, Serialize, Deserialize, Default)]
@@ -43,12 +43,7 @@ impl Cli {
     })
   }
 
-  async fn handle(
-    &self,
-    runtime: Runtime,
-    operation: Entity,
-    args: Vec<String>,
-  ) -> Result<StructuredOutput, RuntimeError> {
+  async fn handle(&self, runtime: Runtime, operation: Entity, args: Vec<String>) -> Result<(), RuntimeError> {
     let is_interactive = Interactive {
       stdin: atty::is(atty::Stream::Stdin),
       stdout: atty::is(atty::Stream::Stdout),
@@ -72,12 +67,24 @@ impl Cli {
           Ok(p) => {
             if p.port() == "code" && p.has_data() {
               let code: u32 = p.decode().unwrap();
-              break StructuredOutput::new(format!("Exit code: {}", code), json!({ "code": code }));
+              let message = if code > 0 {
+                format!("Exit code: {}", code)
+              } else {
+                String::new()
+              };
+              break StructuredOutput::new(message, json!({ "code": code }));
+            }
+            if p.is_error() {
+              let err = p.unwrap_err();
+              break StructuredOutput::new(
+                format!("CLI Trigger produced error, {}", err.msg()),
+                json!({ "error": err.to_string() }),
+              );
             }
           }
           Err(e) => {
             break StructuredOutput::new(
-              format!("CLI Trigger produced error: {}", e),
+              format!("CLI Trigger produced error, {}", e),
               json!({ "error": e.to_string() }),
             );
           }
@@ -90,9 +97,9 @@ impl Cli {
       }
     };
 
-    let _ = self.done_tx.lock().take().unwrap().send(());
+    let _ = self.done_tx.lock().take().unwrap().send(output);
 
-    Ok(output)
+    Ok(())
   }
 }
 
@@ -134,9 +141,9 @@ impl Trigger for Cli {
     Ok(())
   }
 
-  async fn wait_for_done(&self) {
+  async fn wait_for_done(&self) -> StructuredOutput {
     let rx = self.done_rx.lock().take().unwrap();
-    let _ = rx.await;
+    rx.await.unwrap_or_default()
   }
 }
 
diff --git a/crates/wick/wick-runtime/src/triggers/http.rs b/crates/wick/wick-runtime/src/triggers/http.rs
index 71724e27..45f62dee 100644
--- a/crates/wick/wick-runtime/src/triggers/http.rs
+++ b/crates/wick/wick-runtime/src/triggers/http.rs
@@ -193,16 +193,30 @@ impl Trigger for Http {
     Ok(())
   }
 
-  async fn wait_for_done(&self) {
+  async fn wait_for_done(&self) -> StructuredOutput {
     let rx = if let Some(instance) = self.instance.lock().as_mut() {
       instance.running_rx.take()
     } else {
       None
     };
     if let Some(rx) = rx {
-      let _ = rx.await;
+      match rx.await {
+        Ok(_) => {
+          info!("http trigger finished");
+          StructuredOutput::new("http trigger finished", json!({"status": "http trigger finished"}))
+        }
+        Err(e) => {
+          error!(err=%e,"http trigger failed");
+          let message = format!("http trigger failed: {}", e);
+          StructuredOutput::new(format!("http trigger failed: {}", e), json!({"status": message}))
+        }
+      }
     } else {
       error!("http trigger not running");
+      StructuredOutput::new(
+        "http trigger not running",
+        json!({"status": "http trigger not running"}),
+      )
     }
   }
 }
diff --git a/crates/wick/wick-runtime/src/triggers/time.rs b/crates/wick/wick-runtime/src/triggers/time.rs
index 04568a07..0576888b 100644
--- a/crates/wick/wick-runtime/src/triggers/time.rs
+++ b/crates/wick/wick-runtime/src/triggers/time.rs
@@ -171,17 +171,21 @@ impl Trigger for Time {
     Ok(())
   }
 
-  async fn wait_for_done(&self) {
+  async fn wait_for_done(&self) -> StructuredOutput {
     let Some(handler) = self.handler.lock().take() else {
-      return;
+      return StructuredOutput::new("scheduled job never ran", json!({"status": "schedule job never ran"}));
     };
 
     match handler.await {
       Ok(_) => {
-        info!("cron done");
+        info!("time trigger done");
+        StructuredOutput::new("scheduled job complete", json!({"status": "schedule job complete"}))
       }
       Err(e) => {
-        error!("cron error: {}", e);
+        error!(err=%e,"time trigger error");
+        let message = format!("time trigger error: {}", e);
+        let json = json!({"error": message});
+        StructuredOutput::new(message, json)
       }
     }
   }
diff --git a/src/commands/run.rs b/src/commands/run.rs
index be4420f8..1836de9b 100644
--- a/src/commands/run.rs
+++ b/src/commands/run.rs
@@ -70,14 +70,28 @@ pub(crate) async fn handle(
     .span(span.clone())
     .build()?;
 
-  if !opts.dryrun {
+  let output = if !opts.dryrun {
     host.start()?;
     span.in_scope(|| debug!("waiting on triggers to finish..."));
 
-    host.wait_for_done().instrument(span.clone()).await?;
+    let output = host.wait_for_done().instrument(span.clone()).await?;
+    let mut lines = String::new();
+    let mut json = Vec::new();
+    for output in output {
+      if !output.lines.trim().is_empty() {
+        lines.push_str(&output.lines);
+        lines.push('\n');
+      }
+      json.push(output.json);
+    }
+    StructuredOutput::new(lines, json!({"output":json}))
   } else {
     info!("application valid but not started because --dryrun set");
-  }
+    StructuredOutput::new(
+      "application valid but not started because --dryrun set",
+      json!({"status":"valid"}),
+    )
+  };
 
-  Ok(StructuredOutput::new("", json!({})))
+  Ok(output)
 }