We often get asked whether Cloud Drive Mapper has an auto-update feature. While it is on our roadmap for the future, it's not currently available. Even in future when it is available as a feature, it would never be the default behaviour. We understand the convenience of auto-updates, but for CDM, we feel a manual upgrade is (in most cases) more appropriate.
Cloud Drive Mapper is a highly-integrated product, and it requires different elements across your local machines/VDIs, firewall, proxies, Azure AD (or third party SSO provider), and inside Office 365 itself to all unite in harmony for it to work seamlessly.
When we make changes to Cloud Drive Mapper, especially epic/major releases (documented in our changelog) we always recommend testing the new client in a sandbox / non-production setting first, just to sense-check it, and confirm that it does still seamlessly work in your environment. It is also worthwhile making sure you do quickly read the changelog notes before you update as well, so you have some ideas about what changes have been made. We try to make them as detailed and explanatory as possible.
We put a lot of effort trying to cover as many scenarios as we can with our internal testing - we have an advanced automated test suite as well as over 25 different lab environments that CDM has to successfully pass manual testing on before it can even be released to a beta. But given the almost infinite number of combinations of different environmental variables, it is a good idea for customers to check it works in the way you expect it to before taking the plunge.
99% of the time it will just work as you expect and there's nothing to worry about, but it's worth taking the extra effort to avoid the 1% of cases that could end up causing headaches for your users.
Do we always need to update?
No. Critical updates are incredibly rare when it comes to Cloud Drive Mapper. Some of our customers are perfectly happy using versions of Cloud Drive Mapper back to 1.5/1.6 which are about 3 years old. "If it ain't broke, why fix it?"
But of course, with many updates we have brought a range of improvements to the product, we've added new features, and enhanced its compatibility with Azure AD, MFA, as well as adapted to changes within Office 365.
It is not a bad idea to try to stay reasonably up-to-date, but you don't really need to worry about it.
If there ever were a situation warranting a critical update, we would directly communicate with all our customers and partners to make sure they were aware of the issues and had the relevant guidance.
About the update process itself
We can't really give generic advice for this because the update process will depend on how you deployed the client in the first place. But with the MSI, it should be really straightforward to redeploy the new version over the old and it will just take the update. There shouldn't be any more complexity to it than that. If you have any technical questions about it though, as with anything else related to our products, our support team is available to help so please reach out to firstname.lastname@example.org and they will be able to guide you accordingly.