In the current scenario, the Outlook synchronization filters, both User and System only control the data flow from CRM to Outlook and not the other way round.

For e.g., Let us say we have a filter which checks if the owner "does not contain data", which in a way is stopping the sync from CRM to outlook as all records in CRM will have a owner.

User creates a contact in outlook and tracks it. This contact gets created in CRM irrespective of the filter. When the contact is updated in CRM, no updates are pushed to Outlook, but when the contact is updated in Outlook, it does flow back into CRM.

Suggestions would be to make the filter bidirectional to keep the design consistent.

Regards