diff --git a/Cargo.lock b/Cargo.lock
index 7b3db1e49e..24952a4988 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -1332,7 +1332,7 @@ checksum = "613afe47fcd5fac7ccf1db93babcb082c5994d996f20b8b159f2ad1658eb5724"
 
 [[package]]
 name = "chat-cli-ui"
-version = "1.19.2"
+version = "1.19.3"
 dependencies = [
  "chrono",
  "crossterm",
@@ -1359,7 +1359,7 @@ dependencies = [
 
 [[package]]
 name = "chat_cli"
-version = "1.19.2"
+version = "1.19.3"
 dependencies = [
  "amzn-codewhisperer-client",
  "amzn-codewhisperer-streaming-client",
@@ -6366,7 +6366,7 @@ dependencies = [
 
 [[package]]
 name = "semantic_search_client"
-version = "1.19.2"
+version = "1.19.3"
 dependencies = [
  "anyhow",
  "bm25",
diff --git a/Cargo.toml b/Cargo.toml
index 21303957a8..69a554c5f6 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -8,7 +8,7 @@ authors = ["Amazon Q CLI Team (q-cli@amazon.com)", "Chay Nabors (nabochay@amazon
 edition = "2024"
 homepage = "https://aws.amazon.com/q/"
 publish = false
-version = "1.19.2"
+version = "1.19.3"
 license = "MIT OR Apache-2.0"
 
 [workspace.dependencies]
diff --git a/crates/chat-cli-ui/src/conduit.rs b/crates/chat-cli-ui/src/conduit.rs
index e347b9da30..37706e56f2 100644
--- a/crates/chat-cli-ui/src/conduit.rs
+++ b/crates/chat-cli-ui/src/conduit.rs
@@ -15,6 +15,7 @@ use crate::legacy_ui_util::ThemeSource;
 use crate::protocol::{
     Event,
     LegacyPassThroughOutput,
+    MetaEvent,
     ToolCallRejection,
     ToolCallStart,
 };
@@ -53,6 +54,7 @@ impl ViewEnd {
     pub fn into_legacy_mode(
         self,
         theme_source: impl ThemeSource,
+        prompt_ack: Option<std::sync::mpsc::Sender<()>>,
         mut stderr: std::io::Stderr,
         mut stdout: std::io::Stdout,
     ) -> Result<(), ConduitError> {
@@ -153,7 +155,17 @@ impl ViewEnd {
                 Event::ReasoningMessageEnd(_reasoning_message_end) => {},
                 Event::ReasoningMessageChunk(_reasoning_message_chunk) => {},
                 Event::ReasoningEnd(_reasoning_end) => {},
-                Event::MetaEvent(_meta_event) => {},
+                Event::MetaEvent(MetaEvent { meta_type, payload }) => {
+                    if meta_type.as_str() == "timing" {
+                        if let serde_json::Value::String(s) = payload {
+                            if s.as_str() == "prompt_user" {
+                                if let Some(prompt_ack) = prompt_ack.as_ref() {
+                                    _ = prompt_ack.send(());
+                                }
+                            }
+                        }
+                    }
+                },
                 Event::ToolCallRejection(tool_call_rejection) => {
                     let ToolCallRejection { reason, name, .. } = tool_call_rejection;
 
diff --git a/crates/chat-cli/src/cli/chat/mod.rs b/crates/chat-cli/src/cli/chat/mod.rs
index e1eab6ddd6..5ba5b36317 100644
--- a/crates/chat-cli/src/cli/chat/mod.rs
+++ b/crates/chat-cli/src/cli/chat/mod.rs
@@ -605,6 +605,7 @@ pub struct ChatSession {
     inner: Option<ChatState>,
     ctrlc_rx: broadcast::Receiver<()>,
     wrap: Option<WrapMode>,
+    prompt_ack_rx: std::sync::mpsc::Receiver<()>,
 }
 
 impl ChatSession {
@@ -630,11 +631,12 @@ impl ChatSession {
         let should_send_structured_msg = should_send_structured_message(os);
         let (view_end, _byte_receiver, mut control_end_stderr, control_end_stdout) =
             get_legacy_conduits(should_send_structured_msg);
+        let (prompt_ack_tx, prompt_ack_rx) = std::sync::mpsc::channel::<()>();
 
         tokio::task::spawn_blocking(move || {
             let stderr = std::io::stderr();
             let stdout = std::io::stdout();
-            if let Err(e) = view_end.into_legacy_mode(StyledText, stderr, stdout) {
+            if let Err(e) = view_end.into_legacy_mode(StyledText, Some(prompt_ack_tx), stderr, stdout) {
                 error!("Conduit view end legacy mode exited: {:?}", e);
             }
         });
@@ -739,6 +741,7 @@ impl ChatSession {
             inner: Some(ChatState::default()),
             ctrlc_rx,
             wrap,
+            prompt_ack_rx,
         })
     }
 
@@ -1942,6 +1945,25 @@ impl ChatSession {
 
         execute!(self.stderr, StyledText::reset(), StyledText::reset_attributes())?;
         let prompt = self.generate_tool_trust_prompt(os).await;
+
+        // Here we are signaling to the ui layer that the event loop wants to prompt user
+        // This is necessitated by the fact that what is actually writing to stderr or stdout is
+        // not on the same thread as what is prompting the user (in an ideal world they would be).
+        // As a bandaid fix (to hold us until we move to the new event loop where everything is in
+        // their rightful place), we are first signaling to the ui layer we are about to prompt
+        // users, and we are going to wait until the ui layer acknowledges.
+        // Note that this works because [std::sync::mpsc] preserves order between sending and
+        // receiving
+        self.stderr
+            .send(Event::MetaEvent(chat_cli_ui::protocol::MetaEvent {
+                meta_type: "timing".to_string(),
+                payload: serde_json::Value::String("prompt_user".to_string()),
+            }))
+            .map_err(|_e| ChatError::Custom("Error sending timing event for prompting user".into()))?;
+        if let Err(e) = self.prompt_ack_rx.recv_timeout(std::time::Duration::from_secs(10)) {
+            error!("Failed to receive user prompting acknowledgement from UI: {:?}", e);
+        }
+
         let user_input = match self.read_user_input(&prompt, false) {
             Some(input) => input,
             None => return Ok(ChatState::Exit),
diff --git a/crates/chat-cli/src/cli/feed.json b/crates/chat-cli/src/cli/feed.json
index 938d58abac..52ae369009 100644
--- a/crates/chat-cli/src/cli/feed.json
+++ b/crates/chat-cli/src/cli/feed.json
@@ -10,6 +10,18 @@
       "hidden": true,
       "changes": []
     },
+    {
+      "type": "release",
+      "date": "2025-10-29",
+      "version": "1.19.3",
+      "title": "Version 1.19.3",
+      "changes": [
+        {
+          "type": "fixed",
+          "description": "Racing condition between prompting and printing - [#3308](https://github.com/aws/amazon-q-developer-cli/pull/3308)"
+        }
+      ]
+    },
     {
       "type": "release",
       "date": "2025-10-28",