Outlook to Zoho sync

Outlook to Zoho sync

I am the admin for our company and I have (1) single user that is having difficulties with her emails syncing. I have found where the problem is, but I don't know 100% if what is happening is how the plug-in works or if it's a setup issue.

My boss created a parameter that in order to move a deal from qualifications to identify decision maker, the teams needs to send an email. In Zoho, she has 19 emails including emails she's sent as well as received, but it still isn't letting her change the stage. 
We went in an I had her grab a sent email for a deal, click on the plugin in outlook, select the correct module and save. It is only then, that she can move the deal to the next stage.

Long story, short - In order to have an email validated to let her move to the next step, does she need to use the zoho plug-in in outlook for the very FIRST sent email? 
Like I had mentioned, Zoho has all her emails already.

We tried support but they were trying to fix something that was not the issue, no matter how we described it. Our blueprint hasn't changed in months and the issue just started.