I am having troubles uploading IPS Setup recordings. When I make a recording, it appears followed by an exclamation point in a square, meaning that, according to this page, that “[t]he upload failed. IPS Setup automatically tries to upload these recordings when a stable internet connection is available.”
Is your IPS map shared with ArcGIS Online or ArcGIS Enterprise?
If it's the latter case, you may want to make sure that .pb files are accepted for uploads by following the instructions described at https://community.esri.com/t5/arcgis-ips-documents/extending-arcgis-enterprise-with-necessary-data/t...
These steps should only be necessary with ArcGIS Enterprise 10.9.x. Starting with ArcGIS Enterprise 11.0, .pb file upload is enabled by default.
It would also be great if you could specify details about your data - i.e. which version of Enterprise do you have.
Thanks