Give every photo a clear job
A useful filename tells you which lot a photo belongs to and where it falls in that lot's sequence. For example, 200_1.jpg can be the overall view of lot 200, followed by 200_2.jpg for a detail and 200_3.jpg for a condition photograph.
Use the same convention for the entire auction. Avoid changing between dashes, spaces and underscores halfway through a folder. If your auction software requires a particular format, use that format as your starting point.
Make a working copy first
Keep the original camera files in a folder you will not rename. Copy the photos you want to process into a separate working folder. This gives you a way to trace an image back to the camera sequence if files get moved into the wrong lot.
Sort the working folder and review the order before renaming. File order can change when names mix ordinary numbers and text, so look at the first, middle and last few files rather than assuming everything is correct.
Test the pattern on a small group
Use the desktop tool's rename preview before applying your changes. Start with two or three lots, including at least one lot with several images. Confirm that each resulting name is unique and that the numbering follows your intended order.
A filename should organize a photograph, not replace a description. Keep condition notes, dimensions and provenance with the lot record rather than trying to squeeze everything into a filename.
Verify before cataloging
Open the renamed photos and compare them with your lot list. Check that groups and sets have not been split, that the cover image comes first, and that close-ups have stayed with the right item.
If you also resize or convert formats, inspect the resulting photos at full size. Make sure small labels remain legible. Once the sample looks right, process the remaining working files and keep your original folder until the sale and any follow-up questions are complete.
BBZ Image Tools