Data security, scale, speed, and flexibility are the main ones we run into.
Cloud is hosted in the US, and some users suffer from latency problems with it.
I'm European, and we have varyingly levels of data protection - across the continent, you have to check with lawyers before you can store certain types of personal data on US servers, and you're responses will vary from the low-end "nothing medical" through to "nope, it's all illegal, not even an email address". Not having European data centres is a huge reason for being forced to self-host.
Cloud only handles up to 2,000 users. I regularly work with systems with tens of thousands.
Finally, and arguably the biggest reason (alongside "it's illegal"), flexibility. Connect add-ons are great, but they simply don't (yet) have anywhere near the level of functionality to enable people to use many of the most powerful add-ons, or write their own custom stuff that can make Atlassian stuff do exactly what they need. It's rare we come across someone who wants to move to Cloud and drop their add-ons. It's common for us to be converting people off Cloud so that they can use add-ons Cloud doesn't support.
Thank you. So it sounds like you are recommending to not do the $10 (my team has 10 members) monthly hosting in the cloud but rather the one time $10 fee to host on my own server?
Are there additional costs associated with this? Or is it just the one-time $10 fee?
Actually, no. For a small team, or those new to Atlassian, I would very strongly recommend the use of Cloud.
The legal side is probably going to be fine, unless you're storing personal data. Scale will be fine for 10 users, and most people do not have speed issues with it. On the "flexibility" thing, a team new to Atlassian won't know about limitations up-front, and even the more familiar users won't need that flexibility in a lot of cases.
In other words, you won't really know until you try it!
As a practical consideration: Cloud works almost instantly. Pay the initial $10, it'll be there in less than an hour and you don't need to think about looking after it. Self-hosting means you've got to find a machine, install it, and worry about backups, disasters, email servers etc etc etc.
I'd say "try Cloud first". If it turns out not to work for you, then transferring your data to a server install isn't as hard or scary as it sounds!
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