This is a list of bad features, poor interface design, problems with third-party apps, etc. Known bugs in Sierra 10.12.4 are listed in this article.
Finale 2014d crashing bug
According to Finale support, Finale version 2014d becomes unstable in macOS Sierra 10.12.4 (but not previous versions of Sierra), and crashes when a tool with symbol selection (such as Expressions, Articulations) is used. Affected users should contact Finale’s Customer Success team.
RealVNC – Shift key doesn’t work with ARD
Thanks to Joshua Ochs at RealVNC for pointing out a weird bug in Sierra. When using RealVNC to connect to Apple Remote Desktop running on Sierra, the normal Shift key doesn’t work, which can make it very tough to enter a password, for example! Full details and workrounds are given in the RealVNC Knowledge Base. The simplest solution seems to be to install RealVNC’s VNC Server, which doesn’t suffer from this problem.
Dropbox has issues which can result in data loss
The simplest way to avoid problems is to ensure that you only sync documents using Dropbox, or iCloud, but not both. If you want to use both, then ensure that you use the latest version of Dropbox, that its dropbox has the default name of Dropbox, and that you do not move Dropbox to your Desktop or Documents folders. Even then there are other troublesome bugs which can rarely result in data loss.
Remaining problems detailed by Dropbox include the replacement of screenshots taken while Dropbox isn’t running, by .icloud placeholder files, and possible data loss when using symlinks in your Dropbox which point to the Documents folder or Desktop. Dropbox recommends that you do not use symlinks in your Dropbox under any circumstances, as they can lead to data loss even if you get everything else right. Full details are here.
DisplayLink products – largely resolved
There’s a list of problems which have been found when trying to use DisplayLink products with Macs running macOS Sierra here. Updating to version 10.12.4 seems essential, but does resolve many of the previous issues.
File Open and Save dialogs won’t work with pointer (Office 2011 and others)
Trying to navigate the dialogs used to open and save documents using a trackpad/mouse and pointer can prove impossible in many older apps, including Microsoft Office 2011. You can still use the pointer to operate the buttons and other devices, but it may not select items in the inner file browser. macOS Sierra 10.12.2 does improve these issues, but you may still occasionally resort to using the cursor keys.
The workaround is to use the cursor keys instead. Although kludgy, they should still give you full access to the folders and files within the dialog.
Crashes and freezes with TaskExplorer – fixed
Version 1.5.0 (and earlier) of Objective-See’s security and general utility TaskExplorer can, on some macOS Sierra systems, result in crashes or freezes. All users are recommended to update to version 1.6.0, which fixes the issue.
File Open and Save dialogs don’t access iCloud Drive and other favourites (Office 2011 and others)
In the standard dialogs used to open and save documents, the list of items under Favourites may not include new locations such as iCloud Drive. To give access to a folder on your iCloud Drive from those apps, create an alias to it and move that alias into your Documents folder, as described here for Office 2011.
Once you have accessed documents on your iCloud Drive from an older app, it may then decide to add iCloud Drive to its Favourites. This may also be addressed by Sierra 10.12.2.
Crashes in Microsoft Office 2016 apps – mostly resolved
Microsoft acknowledges that some users experience crashes in the various apps of Microsoft Office 2016. These should resolve following updating to Sierra 10.12.2. It also helps if you can turn off (uncheck) Auto Proxy Discovery and Automatic Proxy Configuration in the Proxies pane of your current Network configuration. Details are here.
If your Mac requires that Auto Proxy Discovery and/or Automatic Proxy Configuration are turned on, you must update to Sierra 10.12.2 or later, and even then it seems possible that infrequent crashes might occur, although much less likely.
Adobe CC – now almost completely compatible and fully supported
Printing from Photoshop can result in Photoshop unexpectedly quitting when still running Sierra 10.12.0. Adobe recommends updating to Sierra 10.12.1 or later, and to Photoshop CC 2017, which resolves almost all remaining issues. Full details are here.
Adobe Photoshop Lightroom version 6.8 is now almost entirely compatible with Sierra, with just one minor issue remaining. Further details are here.
Adobe Drive versions 5.0.3 and earlier fail to install on Sierra, and advice to download the Adobe Support Advisor also fails, as Adobe has discontinued that tool. Adobe’s suggested workaround is to not upgrade to Sierra, which is hardly helpful if you already have done that. Details are here.
Adobe has now apparently declared that “the latest versions of all Creative Cloud products” are now compatible with macOS Sierra, and fully support Sierra. Its statement is here.
(Thanks to Simon Simpson for this.)
Fujitsu ScanSnap incompatibility – fully resolved
Users of ScanSnap devices now have full Sierra support, with a list of updates available here. There are also fixes in Sierra 10.12.1 and later, which should make ScanSnap use fully robust again. These now include dealing properly with existing ScanSnap documents – please read Fujitsu’s advice carefully to ensure that yours are properly safeguarded in Sierra.
Adobe CS6 and earlier
Many users are reporting success in running component apps from Adobe CS6 and earlier, even back to CS3 in some cases. However, if you do not install Apple’s legacy Java package from here, some or all the apps may not run at all. Modern Oracle Java does not work for this purpose, but it appears that Apple’s old installer still does. Not that if you had this installed before upgrading to Sierra, you will probably need to reinstall it afterwards.
Cydia Geeks report that they have experienced slow Wi-Fi connections after upgrading to Sierra: it is worth reading their clear and instructive article here. If affected, moving the relevant settings files from /Library/Preferences/SystemConfiguration/ and restarting should clear the problem. The files are: com.apple.airport.preferences.plist, com.apple.network.identification.plist, com.apple.wifi.message-tracer.plist, NetworkInterfaces.plist, and preferences.plist.
This is a generic solution for some WiFi problems, and often worth trying in similar circumstances.
(Thanks to @cydiageeks)
PPTP VPN no longer supported
Buried in the fine print is the news that Sierra no longer supports PPTP VPN. If you cannot switch to a better protocol, such as one based on IPSec or an SSL client, Apple recommends using one of the clients available on the App Store, such as Aruba, Open VPN, etc. There are others too, such as Shimo.
(Thanks to Mark Anderson for drawing my attention to this.)
Problems updating iWork apps after upgrading
Some users report that you need to update from the Purchased page in the App Store app, on some Macs.
Various licensing systems
Some software licensing systems, including previous versions of the nodelocked scheme for Silhouette, stop working in Sierra. Vendors should be providing updates which fix this: for Silhouette, it requires upgrading to version 5, for example.
Updated 6 May 2017.