Uploading map and it ends up rotated 90 degrees on the Table Top.

[Matrim78]

Has anyone had the problem when uploading a map that it ends up sideways or upside down?

[Zacchaeus]

Uploading a map where?

If this is a map that you have found on the Internet or something like that you'll probably need to reorient it in a paint package of some kind if that happens.

[LordEntrails]

Also be aware that in Windows you can 'rotate' an image in the viewer, but this does not actually rotate the image in the file. Open the image in something like Gimp (not Paint, Paint 3D, etc) and see if the orientation is what you expect it to be. If not, rotate and save it there.