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I am building a test Outlook web add-in using office.js. The add-in uses the itemSend event to check various aspects of a message the user is sending. The event works fine. However, if the web server become unavailable, the add-in completely prevents sending any email at all. I cannot find any way around this. I've tried several different ways of trying to first check if the web server is available. Nothing works.

Apparently, Microsoft has disabled itemSend if the web server is not available. But this makes any web add-in developed with itemSend completely unusable because sending email would be shut down for thousands of employees across a company. The fact is that if this is the case, then we have to stick with COM add-ins which are not supported in the confused array of clients aside from classic desktop. Clearly, the office.js approach is nowhere near ready for large scale business use.

Does anyone have any information on whether Microsoft is aware of this and has plans to correct it?

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I am not sure, I will answer your question correctly because there is no real question asked. You have posted your experience that fully matches the description from "On-send feature for Outlook add-ins". So what you are observing when the messages are blocked with add-on implementing onSend feature, when the add-on is unavailable, is absolutely correct. I would probably agree with your statement, that this feature is not sutable for large deployments, but this is not your question as well. And to the last point of your question, I am not Microsoft guy to comment on the future development of "onSend" feature, and most likely nobody would share this information publically. I believe this is the answer to your question, if you had one in your mind.

Now to a suggestion that might be useful for you. As the "onSend" feature was developed and released a few years ago at 1.8 level API and Microsoft didn't improve anything in this area all these years, most likely the dev work here is done. Instead, Microsoft started active development beginning from 1.10 level API on "Event-based activation". The event you are particularly interested in is OnMessageSend and/or OnAppointmentSend. This feature has certain limitations (for example, no Dialog API available for those events, etc.) and there are differences between 'onSend' and 'event-based activation' as well. The main benefit to look at this option is that an add-on implementing event-based activation can be declared in non-blocking mode, so users will not have a problem with sending the messages when add-on is not available.

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Thank you Slava. I have been looking at the OnMessageSend possibility but am concerned about its limitations. However, it may be useable and work sufficiently for web clients. You clarified the situation with itemSend pretty well and I suspect that you are correct in your assessment of the situation with Microsoft no improving on it.
Just for any future reference, it does look like the newer OnMessageSend actually solves the issue I was having with itemSend and a web server being unavailable. In fact, combining this new event with popup messages and even a task pane works quite well.
Glad this helped you, if you think this might help somebody else consider marking my suggestion as an answer.
We have both implementations in our add-on and to be honest, no customer still deployed "onSend" version with reach UI, because of this issue when add-on is unavailable. Instead, we mostly distribute the "Smart Alerts" version based on events and as you mentioned with open taskpane the flow works well, not that reach user experience as with Dialogs, but it works well.

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