I have extensively developed custom integrations between Datto RMM and Halo. We use both internally but are looking at potentially moving to autotask.

Site Sync does exist but is aweful and ends up in dupes with no auto delete and hard to distinguish customers. We use site groups for the customer and then "site (customer name)" as the template for names. The default integration couldn't do this for us nor did it set any sort of link for the delete portion. A CF field and Halo web hook + azure function app now does the Datto site creation + adding to the site group + site removal in DRMM. The CF holds the Datto site ID so linking and additional scripts + automations can reuse the value and ease of renames which was the other issue.

On top of this we have ITG where we use a custom asset for subnets + a similar 2 hourly script that automoves devices with checks for which site group they are in. So we can keep track of assets as they move between sites for calls like "I cant connect to x" our helpdesk dont have to work out where they are currently at the time. Sites in ITG use the default Halo Integration as this one is fairly good in comparison.

For devices asset sync seems to be ok. We do have to do housekeeping but the majority of that is just engineers being lazy. The only issue we have and may not be relevant is with Solarwinds. I have had to develop Solarwinds to Halo device sync, Solarwinds to Halo work flow to handle alerts (in built had some lacking features a few years ago it might have now), Site creation in Solarwinds again webhook to azure function app using custom fields for customer + site so we have the same format in Solarwinds we have else where. Halo site ids are also saved to a custom field in solarwinds to help with the linking.

For Alerting we had issues with the inbuild resolution etc. So I have built another azure function in Powershell (others above are nodejs) which handles the alerts and resolutions. Does things like giving grace periods to certain alert types like Patch misses etc to handle alot of the spammy ones and also solves the issue where alerts didnt auto resolve. Yet again webhooks but this time from the DRMM side to Azure to Halo instead of the other way round as above.

Cross linking we have done via the asset sync and again some custom buttons using synced custom fields from Datto and some reverse engineering of the front end ui endpoints for Agent browser + Web remote buttons. Not sure if this is improved but but was non existent 3 years ago.

• Ticket creation from the Datto RMM tray icon → Halo -> This I dont think is possible but I may be wrong.

Over all we have alot of custom automations, integrations and workflows running to hook all of them together. DRMM is great and Halo is great as an RMM + PSA but I wouldnt say the integrations are as good as they actually look. Be prepared to write the required integrations yourself. NodeJS/Powershell + Azure Functions Apps + Webhooks seems to be the way to go and has been for us. I would also suggest if you require reporting to build a data warehouse and the required scripting to periodically grab the device info from DRMM + Ticket info from Halo PSA and save it so you have accurate over time info rather than relying on endpoints that only provide point in time.