On this note,

Are you installing to “/Applications” or “/Users/your-user/Applications”? 
Either should be fine, but if you do have some corruption in your user profile, 
installing to /Applications might help.

Regards,
Adrien

> On Jun 14, 2018, at 2:28 PM, Adrien Monteleone 
> <adrien.montele...@lusfiber.net> wrote:
> 
> Try creating another user account on the Mac. Add GnuCash to dock and see if 
> the problem persists. It might be an issue with prefs files for your user 
> account. If you don’t want to go that route, or in conjunction with doing so, 
> when the question mark appears, try either Force Quitting (technically 
> relaunching) Finder from the apple menu, and/or execute a “killall Dock” 
> command from a terminal. That might give you the reset needed. Also, keep 
> Console.app running and check it when the question mark appears to see if 
> there are any related entries.
> 
> Regards,
> Adrien
> 
>> On Jun 14, 2018, at 2:15 PM, Glen Byram (Gmail) <glen83...@gmail.com> wrote:
>> 
>> Yes, it certainly is annoying. As we speak, Gnucash has just got its grey 
>> question mark. The machine has been woken up for about the 10th time since I 
>> last did "Keep in Dock". No full restart in that time (I rarely do with the 
>> mac). No issue at all the previous 9 or so "wake-ups. I am starting to think 
>> that something is wrong with this specific Mac. I would definitely think 
>> that was the case if other apps had the same issue, but they all work fine.
>> Regards
>> Glen
>> 
>> 
>> On 14/06/2018, 15:07, "gnucash-user on behalf of Adrien Monteleone" 
>> <gnucash-user-bounces+glen83501=gmail....@gnucash.org on behalf of 
>> adrien.montele...@lusfiber.net> wrote:
>> 
>>   I don’t think a second executable is the issue. I frequently see this 
>> problem with Firefox. Occasionally after it updates and re-launches, it will 
>> drop a new icon on the far right of my dock for that updated instance. I 
>> just close it and relaunch it as normal with the original icon. (which uses 
>> the updated instance, there is no older executable anywhere, even if I 
>> clicked that original icon while the other was still open.)
>> 
>>   I don’t have even a guess as to why this is happening though once 
>> GnuCash’s launcher is stored in the dock via right-click and ’keep in dock.’
>> 
>>   Regards,
>>   Adrien
>> 
>>> On Jun 13, 2018, at 6:56 AM, David T. via gnucash-user 
>>> <gnucash-user@gnucash.org> wrote:
>>> 
>>> My dock works, and has worked for a decade. Perhaps you are using GnuCash 
>>> from two places: Applications, and the dmg? I say this because the “?” 
>>> could happen after restart if the dock item were linked to a dmg file, and 
>>> the dmg weren’t reloaded on restart. 
>>> 
>>> Similarly, a second dock item would suggest a second executable in a 
>>> different location—although how the dock item could reference a different 
>>> executable is beyond me. 
>>> 
>>> David T.
>>> 
>>>> On Jun 13, 2018, at 5:56 AM, Glen Byram via gnucash-user 
>>>> <gnucash-user@gnucash.org> wrote:
>>>> 
>>>> I am running macOS Sierra 10.12.6
>>>> 
>>>> I cannot get Gnucash to reside in the mac dock like other apps. I may have 
>>>> reported this issue before but I can’t find anything in gnucash-user and 
>>>> whatever solution I thought I had was only temporary.
>>>> 
>>>> 
>>>> 
>>>> 1)  The normal process for placing an app into the dock permanently is to 
>>>> just drag it from the place it is installed (usually the Applications 
>>>> folder) to a position on the dock that you want.
>>>> 
>>>> Once this is done, you should be able to launch the app from the resulting 
>>>> dock icon. The same icon should bounce as it launches, then stop with a 
>>>> dot under the icon to show it is active.
>>>> 
>>>> The behaviour I see is that a duplicate Gnucash icon appears at the end of 
>>>> the dock and it is this one that bounces/indicates active app. Although 
>>>> functionally OK, I don’t want 2 icons for the same app when its running 
>>>> one instance.
>>>> 
>>>> 
>>>> 
>>>> 2) I have tried the alternate method of keeping Gnucash in the dock; Make 
>>>> sure there are no Gnucash dock icons then launch it directly from the 
>>>> Applications folder. Once launched, right click on the active dock icon 
>>>> and select Options->Keep in dock. After that, I can move the icon to the 
>>>> position in the dock I want it to be. It now appears to work perfectly. 
>>>> Unfortunately, after I log out, or after some periods of sleep (not sure 
>>>> on the number-seems random) the Gnucash icon gets overlayed with a 
>>>> question mark indicating that the location of the app is now unknown – 
>>>> even though it has not changed and is still in the Applications folder. If 
>>>> I restart the machine when the Gnucash icon is working as expected, I get 
>>>> a grey question mark in the dock without even the Gnucash icon. Mousing 
>>>> over the grey question mark gives a Gnucash tooltip but of course it won’t 
>>>> launch as the location of Gnucash is unknown. The only option is to right 
>>>> click on the icon+question mark or question mark (by itself) and select 
>>>> Options->Remove from Dock.
>>>> 
>>>> 
>>>> 
>>>> As far as I can tell Gnucash is the only App I have that exhibits this 
>>>> behaviour. At the start, I thought I had fixed it using method 2 above. 
>>>> Then after several days the dreaded question mark appeared over the icon.
>>>> 
>>>> Other things I have tried include making an Alias for Gnucash and dragging 
>>>> that to the dock. It didn’t work and behaved like 1) above (duplicate app 
>>>> icon on launch).
>>>> 
>>>> I decided maybe the dock was corrupt so I did a reset to default: Terminal 
>>>> command; “defaults delete com.apple.dock; killall Dock”
>>>> 
>>>> This meant I had to rebuild my preferred dock from scratch. There was no 
>>>> difference. All other app icons behaved as expected apart from Gnucash.
>>>> 
>>>> 
>>>> 
>>>> My conclusion is that Gnucash must have a launch process different to 
>>>> other apps and/or the drag/drop to dock processing must be different.
>>>> 
>>>> For the time being I tend to stick to Option 2 above as I prefer a single 
>>>> launch icon on the dock. When Gnucash eventually gets it’s inevitable 
>>>> question mark I remove it from dock then re-instate it as per 2) above. 
>>>> But it would be nice to have no need to do that. It’s not urgent or a 
>>>> matter of life and death but something to ponder.
>>>> 
>>>> 
>>>> 
>>>> Cheers
>>>> 
>>>> Glen
>>>> 
>>>> 
>>>> 
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