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ArcGIS honors the Addin that was most recently added to the Well-Known folder, even if it is more outdated than the current Add-in.
I tested the below workflow on ArcGIS 10.3.1 to reach the above conclusion.
1- Create an Addin called ArcMapAddin1 in Visual Studio, and create a button that pops up a message box that reads "This is Addin1 before an update". Build your Visual Studio project so as to output the *.esriaddin file.
2- Copy the ArcMapAddin1.esriaddinx file from the bin folder to a well-known folder, e.g. C:\Temp
3- Run ArcMap.
4- ArcMap's Addin Manager shows that a "shared-Addin" called Addin1 has been recently installed.
5- From the Customize menu, drag the Addin1 button to a toolbar, and click it.
6- A message box is displayed; as expected, it reads "This is Addin1 before an update"
7- Close ArcMap.
8 - Make a small change to the Addin1 in Visual Studio. Change the Message Box to read "This is an UPDATED Addin1". Clean and rebuild your project so as to output an updated *.esriaddin file in the bin folder of your project.
9 - Copy the updated *.esriaddin file from the bin folder over to a new folder one level below your Well-Known Folder, for example, C:\Temp\Update.
10- Open ArcMap and click the Addin1 button on the toolbar.
11- You should see a message box that reads "This is an UPDATED Addin1".
12- Copy both Addins from the Well-Known folder to a temporary location, e.g. C:\Temp2\Addin1 and C:\Temp2\Addin1\Update.
13- Delete the two Addins from the Well-Known folder
14- Then, copy the Addin in C:\Temp2\Addin1\Update to C:\Temp. This is the most recently created Addin.
15- Run ArcMap and click on the button. You will get the message "This is an UPDATED Addin1".
16- Now, Copy the Addin in C:\Temp2\Addin1 to C:\Temp\Update. This is the more outdated Addin.
17 - Run ArcMap and click on the button. You will get the message "This is Addin1 before an update"
18- Thus, ArcMap honors the Addin that was most recently copied to the Well-Known Folder, regardless of whether it is more outdated than the existing one. It does not honor the date of creation of the Add-in.
ArcGIS honors the Addin that was most recently added to the Well-Known folder, even if it is more outdated than the current Add-in.
I tested the below workflow on ArcGIS 10.3.1 to reach the above conclusion.
1- Create an Addin called ArcMapAddin1 in Visual Studio, and create a button that pops up a message box that reads "This is Addin1 before an update". Build your Visual Studio project so as to output the *.esriaddin file.
2- Copy the ArcMapAddin1.esriaddinx file from the bin folder to a well-known folder, e.g. C:\Temp
3- Run ArcMap.
4- ArcMap's Addin Manager shows that a "shared-Addin" called Addin1 has been recently installed.
5- From the Customize menu, drag the Addin1 button to a toolbar, and click it.
6- A message box is displayed; as expected, it reads "This is Addin1 before an update"
7- Close ArcMap.
8 - Make a small change to the Addin1 in Visual Studio. Change the Message Box to read "This is an UPDATED Addin1". Clean and rebuild your project so as to output an updated *.esriaddin file in the bin folder of your project.
9 - Copy the updated *.esriaddin file from the bin folder over to a new folder one level below your Well-Known Folder, for example, C:\Temp\Update.
10- Open ArcMap and click the Addin1 button on the toolbar.
11- You should see a message box that reads "This is an UPDATED Addin1".
12- Copy both Addins from the Well-Known folder to a temporary location, e.g. C:\Temp2\Addin1 and C:\Temp2\Addin1\Update.
13- Delete the two Addins from the Well-Known folder
14- Then, copy the Addin in C:\Temp2\Addin1\Update to C:\Temp. This is the most recently created Addin.
15- Run ArcMap and click on the button. You will get the message "This is an UPDATED Addin1".
16- Now, Copy the Addin in C:\Temp2\Addin1 to C:\Temp\Update. This is the more outdated Addin.
17 - Run ArcMap and click on the button. You will get the message "This is Addin1 before an update"
18- Thus, ArcMap honors the Addin that was most recently copied to the Well-Known Folder, regardless of whether it is more outdated than the existing one. It does not honor the date of creation of the Add-in.