diff --git a/src-tauri/src/commands/misc.rs b/src-tauri/src/commands/misc.rs
index 61b0b47d6..40a27c80c 100644
--- a/src-tauri/src/commands/misc.rs
+++ b/src-tauri/src/commands/misc.rs
@@ -1002,21 +1002,46 @@ end tell"#,
 
 /// macOS: iTerm2
 #[cfg(target_os = "macos")]
-fn launch_macos_iterm2(script_file: &std::path::Path) -> Result<(), String> {
-    use std::process::Command;
-
-    let applescript = format!(
-        r#"tell application "iTerm"
-    activate
-    tell current window
-        create tab with default profile
-        tell current session
-            write text "bash '{}'"
-        end tell
+fn build_macos_iterm2_applescript(script_file: &std::path::Path) -> String {
+    format!(
+        r#"set launcher_script to "bash '{}'"
+set was_running to application "iTerm" is running
+tell application "iTerm"
+    if was_running then
+        activate
+        if (count of windows) = 0 then
+            create window with default profile
+        else
+            tell current window
+                create tab with default profile
+            end tell
+        end if
+    else
+        activate
+        set waited to 0
+        repeat while (count of windows) = 0
+            delay 0.1
+            set waited to waited + 1
+            if waited >= 30 then exit repeat
+        end repeat
+        if (count of windows) = 0 then
+            create window with default profile
+        end if
+    end if
+    tell current session of current window
+        write text launcher_script
     end tell
 end tell"#,
         script_file.display()
-    );
+    )
+}
+
+/// macOS: iTerm2
+#[cfg(target_os = "macos")]
+fn launch_macos_iterm2(script_file: &std::path::Path) -> Result<(), String> {
+    use std::process::Command;
+
+    let applescript = build_macos_iterm2_applescript(script_file);
 
     let output = Command::new("osascript")
         .arg("-e")
@@ -1727,6 +1752,43 @@ mod tests {
         assert_eq!(command, "cd '/tmp/project O'\"'\"'Brien' || exit 1\n");
     }
 
+    #[cfg(target_os = "macos")]
+    #[test]
+    fn iterm2_applescript_cold_start_avoids_current_window_before_one_exists() {
+        let script = build_macos_iterm2_applescript(Path::new("/tmp/cc_switch_launcher.sh"));
+
+        let cold_start_branch = script
+            .split("else\n        activate")
+            .nth(1)
+            .expect("cold start branch should be present")
+            .split("    end if\n    tell current session")
+            .next()
+            .expect("cold start branch should end before writing command");
+
+        assert!(cold_start_branch.contains("repeat while (count of windows) = 0"));
+        assert!(cold_start_branch.contains("create window with default profile"));
+        assert!(!cold_start_branch.contains("tell current window"));
+        assert!(!cold_start_branch.contains("create tab with default profile"));
+    }
+
+    #[cfg(target_os = "macos")]
+    #[test]
+    fn iterm2_applescript_keeps_new_tab_behavior_for_existing_windows() {
+        let script = build_macos_iterm2_applescript(Path::new("/tmp/cc_switch_launcher.sh"));
+
+        let running_branch = script
+            .split("if was_running then")
+            .nth(1)
+            .expect("already-running branch should be present")
+            .split("else\n        activate")
+            .next()
+            .expect("already-running branch should end before cold start branch");
+
+        assert!(running_branch.contains("if (count of windows) = 0 then"));
+        assert!(running_branch.contains("create window with default profile"));
+        assert!(running_branch.contains("create tab with default profile"));
+    }
+
     #[test]
     fn build_windows_cwd_command_str_uses_cd_for_drive_paths() {
         let command = build_windows_cwd_command_str(r"C:\work\repo");