Excel spreadsheet for birthday email reminders in Calendar

I forgot to ask who the account provider is where you actually store your calendar? For example, is your email hosted by Apple's iCloud, Google, Mircosoft, Yahoo, etc? To check, open Calendar, in "Settings ...", click Accounts at the top. What is listed in that list on the left?

If using an iCloud account to store you calendar information, then your email alert event settings (Set alerts for an event in Calendar on Mac - Apple Support) should never be lost. If using an iCloud account, email reminders should be very reliable.

If however, your calendar is hosted somewhere else, then there is always to chance for an incompatibility or unreliability between Apple Calendar and the way that the provider's server implements alerts settings.

If your calendar is not currently hosted on iCloud, someone here can then help you import your existing calendar events into an iCloud account. Honestly, any other method (such as an Excel file with scripting) is never going to be as reliable as iCloud calendar email alerts.

Apple has a specific setup just for what you want:

1. Open the Contacts app, create or update a contact for each person, and complete the "birthday" field for each (Contacts User Guide for Mac - Apple Support)
2. Show contacts’ birthdays in Calendar on Mac - Apple Support
3. While still in the Calendars app Settings > Alerts > Birthdays > [select an option for reminders]

I just had a closer look at the web version of iCloud Calendar and was shocked to see that it does not even have the option to set an alert by email. That, despite the option clearly being there in Mail on Mac. What that tells me is that the email alerts on the Mac are actually being send from the Mac itself and not from the iCloud server as I thought. As you thought, that means that all sorts of things such as computer sleep could be the cause of your issues, and it will indeed never be completely reliable that way.

Therefore, as hard as this is for me to say, I can recommend a solution that I personally know works. I recommend that you try the web calendar on your Google account to re-create your events and their email reminders. I personally have been using recurring Google calendar events with email reminders for many years (and they are indeed reliable). I only use my Google account through the web browser however. You may run into the same issues if your attempt to use Calendars on Mac to work with Google calendar servers.

The top hit of a google search for "applescript to extract dates from calendar to spreadsheet" gives a fully commented script that looks like it does most of what you want. It took me 2 more minutes to find out how to mail text from a cron job. Have you got Google or do you want me to come over and write/test it for you?

I think you'll still get the same problem because of what the Mac can't do when its lid's closed.

If it were me I'd make sure that all the events had alerts at a time the Mac is likely to be open and/or you're likely to be in front of them. If you still want the email you can, but I'd add a second, normal alert, also to go off at a sensible time. If you've got the events set up as all-day events this should be OK; I agree with you that alerts for all-day events were messed up a few years ago, but they seem to be OK now and I can't remember the last time they didn't work. The main thing that makes them not work is having different alert settings on different devices. If yours still aren't working then check what your settings are across devices - it's the "use these defaults only on this computer" in Mac Calendar settings that you need to make sure is unticked.

If you don't want to do it with cron then this is what I'd do.

1. Put all these Birthday events in their own calendar
2. Change them all from all-day events to events that start at a specific time. If you don't want them cluttering your calendar then this can be midnight.
3. Set the email alerts to go out at a time when the Mac is likely to be turned on. You can set alerts to be any time relative to the event time using the custom settings in alerts.
4. Set up a normal alert too - because alerts work fine now.

1 - you'll have to do manually if you haven't already. It helps with...

2, 3, 4, should be trivial in Applescript and Google will provide you with starting scripts.

Look up Cron Jobs and crontab.

Cron jobs are tasks that run automatically in the background to a schedule.

Cron jobs can do stuff directly or can run scripts.

crontab is the app/utility that creates and manages cron jobs - it's run in Terminal.

I'm not an expert in cron jobs but with a bit of googling I set one up to print a test page every couple of days to stop my printer heads drying out. You could do some googling and work it out yourself or find someone who's already done it - or maybe someone else will be along here with a better idea.

I hadn't programmed for almost half a century, in BASIC, when I had a go at Applescript to help me sort out my Music playlists. I started by finding snippets online. It's a long way from BASIC but the concepts are similar, there are dictionaries for each app on the Mac showing what can be done and if you get stuck you can "record" a set of actions and see what the script looks like to give you a start.

iCloud is a synchronization service which, in the case of Calendar, synchronizes your calendar entries including all the information it can. Email alerts for calendars are device specific - an email can only be sent from an email account that's on the device and it's not inconceivable that a user might have different email accounts on a Mac and, say, a mobile device. I've got an iPod which has got a calendar which I iCloud synch but the iPod has no email accounts. What would a calendar do on the iPod if iCloud synch told it to send an email alert? Similarly, if you were on a PC in an internet cafe (I know they aren't really a thing any more, but) and logged in to iCloud, you could set up a new calendar entry with alerts but if you set an email alert what email account would you set it up to send from? You might have an iCloud email account but many people don't.