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Groupwise. What an ugly, barely functional piece of crap. I'd set notifications for recurring tasks and sometimes it would remind me and then randomly stop for a while. Sending email felt like the early days of AOL. I left for about a year and when I came back, they'd switched to Outlook, which I don't love, but it's miles better than what we had.
The job I worked at for that year had a custom Salesforce thing that made me want to find whoever built it and throw something at them. It was supposed to track what benefits clients were receiving, like SNAP, disability, etc, but it was borderline impossible to read, case notes would cut off, and searches would routinely just not work. It soured me on Salesforce permanently if that's the kind of garbage they're releasing.
Well, now that software is back in my memory again. cries