Make a safe test folder
In Finder, create a folder named Taggy Tagger Test. Put a disposable copy of one JPEG image in it. Add that folder in Taggy Tagger and grant access. Create an automation for the folder. Keep monitoring paused while setting it up.
Select your JPEG file
In the Condition Editor, use New… to create a condition set named JPEG files. Add File Name, choose Extension Is and enter jpg without a dot. If your sample ends in .jpeg, enter jpeg instead. Your changes are saved in the editor.
Checkpoint: the condition set selects your sample. File Type selects categories such as images; exact extensions belong in File Name.

Choose one tag
Use New… to create a workflow named Add Photo tag. Add an Add Tags action. Under Tags to Add, add Photo and choose its color. Your changes are saved in the editor.
Checkpoint: the workflow contains the Photo tag you want to add.
Video text equivalent: add a tag action
In the selected workflow, open +. Select Add Tags, then Add Action. Under Tags to Add, type the tag name. The example enters Red and a red tag appears below the field. In this guide, use Photo and choose your preferred color. This clip shows configuration only; use Play and check Finder to verify tagging.
Connect and preview both parts
Return to the automation’s rule. Select JPEG files as its condition set and Add Photo tag as its workflow. Saving an item in the editor does not attach it to a rule. Preview the condition set with your JPEG, then preview the workflow with the same file.
Checkpoint: the condition matches and the proposed tags include Photo. Previews leave the file unchanged.
Tag your first file
Use the automation’s Play button to process the test folder. In Finder, inspect your sample’s tags.
Success: your JPEG now has the Photo tag. If it does not, follow the troubleshooting steps before adding more conditions.
Try automatic monitoring
Enable monitoring for this automation. Copy another JPEG into the test folder and check its tags. Keep Taggy Tagger running.
Monitoring checks new and changed files. Files already in the folder when monitoring starts need Play.
What each part does
- Condition set
- Selects which files qualify, such as JPEG files.
- Workflow
- Acts on those files, such as adding Photo.
- Rule
- Connects the condition set and workflow.
- Automation
- Runs an ordered list of rules for a chosen folder.
After your first success
Give JPEG and TIFF files different tags next.
Combine conditions and reuse saved items
AND requires every condition to match. OR accepts any matching condition, including files that match more than one. If any enabled condition set on a rule matches, that rule’s workflows run once. Workflow actions run sequentially; actions do not have OR logic.
Reuse a saved condition set or workflow by selecting it on another rule. Attach both parts explicitly. All matching enabled rules run in order; later actions can change earlier tags.
Preview remove and replace actions on disposable copies first. Activity records results but cannot undo changes. Date conditions are checked when a file is processed; they do not schedule a future run.