There is currently an issue with Microsoft Outlook 2016 Click-to-Run. When a user tries to open an attachment or do some other office tasks, Outlook prompts the user to enter their credentials several times. This issue seems to be connected to a recent update to Office.
The following is a blurb taken from a Microsoft forum on the topic:
In Outlook click File, Office Account and note what Channel you are on. To make the command work you need to use a version that was released to that Channel. See the links at the bottom that has the available versions.
If you are on Semi-annual/FRDC you could try this
cd %programfiles%\Common Files\Microsoft Shared\ClickToRun\
officec2rclient.exe /update user updatetoversion=16.0.8201.2158
or
officec2rclient.exe /update user updatetoversion=16.0.8201.2171
For Monthly/Current Channel this is what was previously mentioned as working:
cd %programfiles%\Common Files\Microsoft Shared\ClickToRun\
officec2rclient.exe /update user updatetoversion=16.0.8326.2107
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