@GoatBOT I am nearly certain I have found and fixed the issue. Basically what was happening is, the alarm clock always tries to give a time that's one day (or some other offset that you set in the settings menu) before the "best" timing it can see in the near future. However, for a decent bit of year 27 (and plenty of other timings with other planets), the best window is IMMEDIATELY. What happens then is, the alarm would end up being set a day in the past, which can't happen, so it would just seem like nothing happened. Definitely an oversight on my part when I added in the offset settings.
I just uploaded a fix to the issue, so if you're using CKAN you should see that update soon. What happens now is, the transfer calculator looks whatever amount your offset is into the future; so, if you keep it as the default 1 day, it will only start considering times one day into the future. If that's the best time it can find, then it will create an alarm just a few seconds away, so that you get feedback telling you that now is a good window to launch.