Start with the missing information
“The upload is broken” leaves several possibilities. An error screenshot may reveal a rejected file type. A recording may show when progress pauses. A physical connection problem may need a view of equipment and its surroundings.
Before requesting more media or a call, identify what remains unknown: the expected result, observed behavior and useful context. The next request should test that uncertainty, not simply collect a larger pile of recordings.
For the initial format decision, compare visual support with text-only answers and request a visual only when it resolves uncertainty that the written description cannot.