I have a Workflow, when a document is created in my document List, it updates fields from that document onto a SharePoint List. When I create the document first time, it does not update, however if I do another one – it updates. Why is this?
If you are updating the column by any means using a code & if it is getting updated by System Account, then your workflows will not run. Check if the modified by column value is ‘System Account’ when your workflow fails.
When you mentioned you do another file upload – did you mean an item with a similar filename, or a totally different file?