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macOS Catalina reminders do not sync with Synology caldav server

With macOS Catalina 1.15.2 reminders do not sync with Synology Caldav server. iOS 13 does, but Catalina won't. Calendar sync with that server is working though on all devices with iOS or Catalina.


Looking into the logs of Catalina I noticed that remindd gets a 405 HTTP Error response at regular intervals. I guess this is generated by the Synology server.

iMac 27", macOS 10.15

Posted on Jan 3, 2020 8:45 AM

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Posted on Jan 6, 2020 6:30 AM

I don't think the linked thread fully explains the problem @tallinn1960 is seeing. I am experiencing the same problem.


CalDAV sync iOS 13.3 <- -> Synology NAS: works

CalDAV sync macOS 10.15.2 <- -> Synology NAS: broken


Discussion 250658735 is about the discrepancy between migrating an iCloud based reminders database to the new format and the timing problem Apple introduced by not releasing iOS 13 and macOS 10.15 simultaneously, leaving users with broken setups and no proper warning dialogs before initiating the breakage. Apple also does not clearly communicate that the new reminders features are limited to the new database format and that new database format is limited to iCloud databases.


I migrated to iOS 13 and was excited about subitems (the most basic feature for any Todo-Software) being introduced to the reminders app. I was never asked to upgrade the database and I never found out how to use subitems. I assume that is because I am not using iCloud and it seems CalDAV users with non-iCloud databases are not migrated. That is acutally a good thing because that way I can continue to user reminders.


Or so I thought. Upgraded to macOS 10.15.2 and discovered Apple deliberately or by accident broke CalDAV sync for reminders - even in the old database format.


Apple has created quite the mess. I sincerely hope they can clean this up sooner than later. Engineering is aware of this problem. I hope they don't ignore it for months to come.

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Question marked as Best reply

Jan 6, 2020 6:30 AM in response to tallinn1960

I don't think the linked thread fully explains the problem @tallinn1960 is seeing. I am experiencing the same problem.


CalDAV sync iOS 13.3 <- -> Synology NAS: works

CalDAV sync macOS 10.15.2 <- -> Synology NAS: broken


Discussion 250658735 is about the discrepancy between migrating an iCloud based reminders database to the new format and the timing problem Apple introduced by not releasing iOS 13 and macOS 10.15 simultaneously, leaving users with broken setups and no proper warning dialogs before initiating the breakage. Apple also does not clearly communicate that the new reminders features are limited to the new database format and that new database format is limited to iCloud databases.


I migrated to iOS 13 and was excited about subitems (the most basic feature for any Todo-Software) being introduced to the reminders app. I was never asked to upgrade the database and I never found out how to use subitems. I assume that is because I am not using iCloud and it seems CalDAV users with non-iCloud databases are not migrated. That is acutally a good thing because that way I can continue to user reminders.


Or so I thought. Upgraded to macOS 10.15.2 and discovered Apple deliberately or by accident broke CalDAV sync for reminders - even in the old database format.


Apple has created quite the mess. I sincerely hope they can clean this up sooner than later. Engineering is aware of this problem. I hope they don't ignore it for months to come.

Jan 8, 2020 12:49 AM in response to AutoZuLaut

The changes introduced to the reminders app with Catalina and iOS/iOSPad 13 affect (or at least are supposed to affect) iCloud-Reminders only.


But I am not yet convinced that the reminders app on Catalina is broken as I found (on the internet) that reminders hosted by nextcloud systems sync with Catalina (at least for some people). I will look into that on my own as nextcloud can run on my Synology disc station.


Got an Apple Watch just yesterday. Which happily showed me the reminders stored on my disc station like my iPhone and iPad do. Not sure wether that counts as CalDav-compability or the watch pulling the data from my iPhone.


Jan 8, 2020 2:05 AM in response to tallinn1960

Nothing in Catalina is broken, just different. If you want mac and phone to sync reminders they need to be the same format. ie

ios13 non upgraded reminders with Mojave or

ios13 upgraded reminders with Catalina


icloud is the normal way to sync but apple watches without cellular are different.


CalDav incompatibility affects non-Apple infrastructure such as in the original post.

Jan 14, 2020 12:40 PM in response to tallinn1960

To follow up:


I tested Catalina reminders with a Nextcloud server and those reminders do sync with this server using caldav. I can see them appearing on the server.


After all it would be a bug to offer the setup of CalDav-accounts on Catalina for both Calendar and Reminders and than not to support the CalDav-Reminders.


The weird thing is that now iOS won't play with Nextcloud. According to the internet wisdom this is caused by my Nextcloud server not having a sound TLS certificate. iOS reminders seems to be more picky about the certificate than iOS calendar and Catalina calendar and reminders are.


So the resolution to my particular problem may be to drop the Synology Calendar Server and replace it with a Nextcloud server (it is possible to install Nextcloud on Synology). The Synology Disc Station has a LE TLS certificate and so everything should be nice with both iOS and Catalina.

macOS Catalina reminders do not sync with Synology caldav server

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