1. Get one JPEG working
Follow Tag your first file in a dedicated Taggy Tagger Test folder with disposable copies. Continue when Play adds Photo to your JPEG.
2. Include both JPEG extensions
Edit JPEG files. Add a second File Name condition. Set Extension Is to jpeg. Keep jpg in the first condition and join the two with OR.
Enter one extension per condition, without a dot. Extension matching ignores case, so JPG also matches jpg. Preview both .jpg and .jpeg samples.
3. Add a TIFF condition set
Create TIFF files with File Name > Extension Is > tif OR File Name > Extension Is > tiff. The editor saves your changes.
4. Add a Print workflow
Create Add Print tag. Add Add Tags. Under Tags To Add, add Print and choose its color. The editor saves your changes. Each distinct tag can have its own color.
5. Attach a second rule
In the same automation, add a second rule. Select TIFF files as its condition set and Add Print tag as its workflow. Keep the first rule connected to JPEG files and Add Photo tag.
6. Check both results
Preview the condition sets and workflows with disposable JPEG and TIFF copies. Run Play, then check Finder: JPEG has Photo; TIFF has Print. Add Tags keeps other existing tags.
Enable monitoring only after both results are correct. Copy fresh samples into the folder to test automatic tagging. Troubleshoot a missing tag.