diff --git a/codex-rs/tui/src/app.rs b/codex-rs/tui/src/app.rs
index 0e155fdc0..8dc2276b7 100644
--- a/codex-rs/tui/src/app.rs
+++ b/codex-rs/tui/src/app.rs
@@ -2939,6 +2939,7 @@ mod tests {
                 app.chat_widget.current_model(),
                 event,
                 is_first,
+                None,
             )) as Arc<dyn HistoryCell>
         };
 
diff --git a/codex-rs/tui/src/chatwidget.rs b/codex-rs/tui/src/chatwidget.rs
index 078fbb978..eb2d1ad96 100644
--- a/codex-rs/tui/src/chatwidget.rs
+++ b/codex-rs/tui/src/chatwidget.rs
@@ -815,6 +815,9 @@ impl ChatWidget {
             &model_for_header,
             event,
             self.show_welcome_banner,
+            self.auth_manager
+                .auth_cached()
+                .and_then(|auth| auth.account_plan_type()),
         );
         self.apply_session_info_cell(session_info_cell);
 
diff --git a/codex-rs/tui/src/history_cell.rs b/codex-rs/tui/src/history_cell.rs
index 934c9506f..eb1de452a 100644
--- a/codex-rs/tui/src/history_cell.rs
+++ b/codex-rs/tui/src/history_cell.rs
@@ -46,6 +46,7 @@ use codex_core::protocol::McpInvocation;
 use codex_core::protocol::SessionConfiguredEvent;
 use codex_core::web_search::web_search_detail;
 use codex_otel::RuntimeMetricsSummary;
+use codex_protocol::account::PlanType;
 use codex_protocol::models::WebSearchAction;
 use codex_protocol::openai_models::ReasoningEffort as ReasoningEffortConfig;
 use codex_protocol::plan_tool::PlanItemArg;
@@ -943,6 +944,7 @@ pub(crate) fn new_session_info(
     requested_model: &str,
     event: SessionConfiguredEvent,
     is_first_event: bool,
+    auth_plan: Option<PlanType>,
 ) -> SessionInfoCell {
     let SessionConfiguredEvent {
         model,
@@ -995,7 +997,7 @@ pub(crate) fn new_session_info(
         parts.push(Box::new(PlainHistoryCell { lines: help_lines }));
     } else {
         if config.show_tooltips
-            && let Some(tooltips) = tooltips::random_tooltip().map(TooltipHistoryCell::new)
+            && let Some(tooltips) = tooltips::get_tooltip(auth_plan).map(TooltipHistoryCell::new)
         {
             parts.push(Box::new(tooltips));
         }
diff --git a/codex-rs/tui/src/tooltips.rs b/codex-rs/tui/src/tooltips.rs
index 1b59eb4f8..b59a478a4 100644
--- a/codex-rs/tui/src/tooltips.rs
+++ b/codex-rs/tui/src/tooltips.rs
@@ -1,9 +1,18 @@
 use codex_core::features::FEATURES;
+use codex_protocol::account::PlanType;
 use lazy_static::lazy_static;
 use rand::Rng;
 
 const ANNOUNCEMENT_TIP_URL: &str =
     "https://raw.githubusercontent.com/openai/codex/main/announcement_tip.toml";
+
+const PAID_TOOLTIP: &str =
+    "*New* Try the **Codex App** with 2x rate limits until *April 2nd*. https://chatgpt.com/codex";
+const OTHER_TOOLTIP: &str =
+    "*New* Build faster with the **Codex App**. Try it now. https://chatgpt.com/codex";
+const FREE_GO_TOOLTIP: &str =
+    "*New* Codex is included in your plan for free through *March 2nd* – let’s build together.";
+
 const RAW_TOOLTIPS: &str = include_str!("../tooltips.txt");
 
 lazy_static! {
@@ -28,11 +37,30 @@ fn experimental_tooltips() -> Vec<&'static str> {
 }
 
 /// Pick a random tooltip to show to the user when starting Codex.
-pub(crate) fn random_tooltip() -> Option<String> {
+pub(crate) fn get_tooltip(plan: Option<PlanType>) -> Option<String> {
+    let mut rng = rand::rng();
+
+    // Leave small chance for a random tooltip to be shown.
+    if rng.random_ratio(8, 10) {
+        match plan {
+            Some(PlanType::Plus)
+            | Some(PlanType::Business)
+            | Some(PlanType::Team)
+            | Some(PlanType::Enterprise)
+            | Some(PlanType::Pro) => {
+                return Some(PAID_TOOLTIP.to_string());
+            }
+            Some(PlanType::Go) | Some(PlanType::Free) => {
+                return Some(FREE_GO_TOOLTIP.to_string());
+            }
+            _ => return Some(OTHER_TOOLTIP.to_string()),
+        }
+    }
+
     if let Some(announcement) = announcement::fetch_announcement_tip() {
         return Some(announcement);
     }
-    let mut rng = rand::rng();
+
     pick_tooltip(&mut rng).map(str::to_string)
 }