Interesting. The dmg shouldn’t matter as the app itself is signed with an Apple 
Developer certificate. You can check that by running
  codesign -vvd /Applications/Gnucash.app

which, if you’re using the latest Mac build, should return
  Executable=/Applications/Gnucash.app/Contents/MacOS/Gnucash
  Identifier=org.gnucash.Gnucash
  Format=app bundle with Mach-O thin (x86_64)
  CodeDirectory v=20200 size=603 flags=0x0(none) hashes=23+3 location=embedded
  Signature size=8523
  Authority=Developer ID Application: John D Ralls (Y9EHT5WMK7)
  Authority=Developer ID Certification Authority
  Authority=Apple Root CA
  Timestamp=Apr 29, 2018 at 9:47:11 PM
  Info.plist entries=19
  TeamIdentifier=Y9EHT5WMK7
  Sealed Resources version=2 rules=12 files=14200
  Internal requirements count=2 size=628

The Authority lines are what’s important.

Regards,
John Ralls

> On Jun 14, 2018, at 5:30 PM, Glen Byram (Gmail) <glen83...@gmail.com> wrote:
> 
> Partially solved! i.e. I think I know what is wrong, but not why it happened 
> to this particular App.
> Short answer: Gnucash is in quarantine due to a Mac OS feature called 
> Gatekeeper Path Randomization (GPR). Running the following command in a 
> Terminal window removes the quarantine flag
> xattr -dr com.apple.quarantine /Applications/Gnucash.app/
> After this command, placing Gnucash in the Dock from the application folder 
> no longer results in a duplicate icon and app behaviour is normal.
> 
> Now, why Gnucash got quarantined in the first place is what I need to work 
> out. It shouldn't happen if an application is copied from the .dmg file to 
> the Applications folder.
> I am currently chaining through the following link where someone was 
> experiencing similar behaviour with an app called Blender. The link pointed 
> me in the right direction for a solution
> https://developer.blender.org/T49473
> 
> I'll report any further findings here if I think it is an issue caused in any 
> way with how the Gnucash .dmg file is built, in case it impacts devs. Now to 
> get to the bottom of GPR on the mac.
> Thanks for all your replies/suggestions
> Glen
> 
> On 14/06/2018, 21:49, "gnucash-user on behalf of Adrien Monteleone" 
> <gnucash-user-bounces+glen83501=gmail....@gnucash.org on behalf of 
> adrien.montele...@lusfiber.net> wrote:
> 
>    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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> 
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