In which forms did you make changes for custom field to appear in Smart IT?
I have implemented all the customization according this article:
Form name WOI:WorkOrder WOI:WorkOrderInterface WOI:WorkOrderInterface_Create WOI:WorkOrder_SLM_Join_Outer INT:WOISLM:SMT_WorkOrder_SLM_Join_Outer
If you create WO directly from Smart IT and update the field in smart it then field appears correctly?
Also in original scenario, when you open WO from smart it (it might not show field value right away) but if wait for some time and try refreshing WO then does it appear after some time without modification?
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You might have already checked this but please check the field name in all Views and make sure that there is no _C added to the display name of the custom field on any of the forms. I had this similar issue because of it, its quite easy to overlook
Second thing you should do is restart the Smart IT services. I had a similar issue on v1.6 where setting the field and retrieving the value from Smart IT only worked after the restart.