One of the macros I use the most involves sending ⌃⌥O to Airmail so that it will send an email message to OmniFocus. It is designed to open the OmniFocus quick-entry inbox, press return, then archive the message.
If it's the first time I invoke the KM macro all day, then it tends to misfire -- it ignores the first part of invoking the quick-entry inbox and then continues to the "archive the message" part. But when I do the macro's steps manually, it works fine. Then, and only then, I can invoke the macro normally and let the computer do its thing. Why does it seem like KM needs to be "woken up" and shown how to do it the first time? I doubt it's an issue with KM itself but I can't figure it out. It's as if every day the macro forgets its script, watches me, then it's good to go. Used to work fine all day every day. Not sure what's changed. Below is the macro for reference.
I don't have your apps, so I can't test.
You might try this: Step through the macro in the Macro_Debugger (KM Wiki). If this works, then it is a strong indication that you have a timing issue.
You many need a more specific Pause Until at the beginning. Sometimes apps open temporary, invisible windows when they start. What is the name of the proper window in OmniFocus when you are ready to proceed?
Thanks for reminding me about the debugger. Totally slipped my mind in this case. It is definitely having issues at steps 1 and 2. But if I do the keystrokes manually, sometimes it works. However, just now when I tried it the keystrokes wouldn’t work until I tried them several times. Starting to think there’s a bug in this release of Airmail (it is a beta release). Seems sluggish to respond to keyboard shortcuts. Will work with the developers to see if they can reproduce. Thanks again for the reminder.