Verison: Spectacle 1.2
OS: macOS Sierra 10.12.5
When I set the "launch spectacle at login" checkbox, it never actually launches at the next login/restart. And when I open spectacle manually, the checkbox is un-ticked again. I feel like this issue is so obvious that I _must_ have just missed something or made a silly error in my settings somewhere. But I have no idea what and I've tried to figure it out, so hopefully it's a fixable bug (or someone can tell me what I'm missing).
I have the same problem on macOS Sierra 10.12.5
same here 10.12.5
me too. Have been using spectacle for years. Same problem.
Hm. First I've heard of this problem. Does Spectacle not show up under "Login Items" for your user under "Users & Groups" in System Preferences when toggled? Any relevant output in the Console app would be helpful as well.
It shows up under login items, but behaving oddly. Here is what it looks like after I first start up and tick the setting:

But after a restart, the login items entry looks like this:

Then when I open Spectacle and tick the (now unticked) setting again, a new copy of it appears in the login items list:

I have this issue as well. Sierra 10.12.6, Spectacle 1.2 (672). Same presentation as @JayAvery's screencaps above.
Edit: Nothing notable found when I searched for "spectacle" in Console.app
I had this issue as well, and I solved it by moving my Spectacle install to the proper applications folder. Double check your install location, might be the issue!
@colleenmcguckin Thanks, I'll try that. What path is yours at?
➜ Spectacle.app pwd
/Applications/Spectacle.app

My spectacle.app was indeed installed in Downloads. Will see if this fixes it.
Le 28 juil. 2017 à 15:06, Jordan Sexton notifications@github.com a écrit :
@colleenmcguckin https://github.com/colleenmcguckin Thanks, I'll try that. What path is yours at?
➜ Spectacle.app pwd
/Applications/Spectacle.app
https://user-images.githubusercontent.com/1173161/28732472-9b28ac68-739d-11e7-995f-17545d9c7a8f.png
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Same problem here!
@jordansexton my install is in ~/Users/colleen/Applications
I just got this computer from a company where someone else set up my user account. For whatever reason I have two Applications folders - one seems to be global and one for my user account? Not exactly sure what happened there. Anyways, my issue was solved when I moved the install to the Applications folder associated with my account. Wasn't a problem on my old machine where there was only one user set up. Hope this helps!
Seeing as this issue was opened up in June is there any fix for this as of today?
I am seeing the same problem. Same visuals in User & Groups as @JayAvery; multiple entries for Spectacle with Unknown in Kind and the yellow alert box.
I have two machines I run the same version (1.2) of Spectacle on:
I have no problems with my personal mac.
I am seeing the issue on my corporate mac.
Searching Console for "spectacle" gives no useful clues; I see some diagnostic entries showing the time the app is using: com.apple.usage.app_activetime but no other clues.
Here is what my Users & Groups looks like:

Any pointers to how to debug this further would be appreciated.
This is super frustrating. I have the same problems as @jmccarrell and @JayAvery and I'm on sierra 10.12.6.
Just chiming in that I've had the same problem. I quit Spectacle, deleted it from Applications, emptied trash and reinstalled the app. Problem fixed, and it now stays in the login items and survives reboots.
I might have installed it at first to ~/Applications, and later moved it to /Applications which _may_ have caused the hiccup.
Note: All my keyboard shortcuts seemed to survive the process, but yours might not.
It turns out that the procedure @chrleon suggested also worked for me. Nice. Thanks @chrleon !
Spectacle might be just installed in Downloads, move it to Applications and that should solve the issue.
For people trying macos for the first time after switching from Windows like me - installing an app seems to be a simple case of unzipping the distribution archive (spectacle.zip) and copying the Spectacle.app bundle to wherever you want it installed (in this case into /Applications/). Then check the Launch Spectacle at login box and voila, it should hopefully work.
How about a feature/enhancement request to 'fix' this in some kind of way. For example some kind of installer or the 'drag to Applications' dialog. Perhaps link to homebrew issue
Unzipping spectacle.zip and then moving it into the /Applications fixes the problem.
drag spectacle file to applications folder
mac settings
add spectacle
right click on spectacle in top bar upper right
launch spectacle at login
restart mac.
worked on
2018 macbook pro 10.14.3
2017 macbook pro 10.13.2
I installed Spectacle via brew cask, which does install the application to /Applications/Spectacle.app. I encounter the problem nonetheless.
There is an /Applications folder and a /Users/<username>/Applications. If I use the former on MacOS Mojave (10.14) it gives the issue specified above. If I use the latter it works. I too used brew cask to install this application so I'm not sure why this issue is happening.
Has this been solved. I am on Catalina now, same issue.
@dbess1 use rxhanson/rectangle instead
Mac OS Big Sur 11.1
I had the same problem but fixed it with Colleen McGuckin's method.(Same as businessph's)
Thank you!
Most helpful comment
Spectacle might be just installed in Downloads, move it to Applications and that should solve the issue.