Pinterest Automatic remains the most feature-rich “auto-pin” tool I’ve found for WordPress. Mapping by tag, category and post-type is superb, and the per-post meta-box lets me hand-pick images and override titles/descriptions when I need fine control. On sites where each post’s images sit in the same month folder as the post itself, it performs flawlessly and cron jobs run with negligible load.

Unfortunately, my workflow involves archival photos whose files live in their original YYYY/MM upload folders while the post is dated today. The plugin rewrites those paths to the post’s current year/month when it builds its internal image list, so every non-featured image shows as a broken link in the editor and fails to pin. Support confirms the path is generated from post_date, so the only reliable workaround is to ① create the post with the photo’s real date, pin, then change the date back, or ② wipe the saved wp_pinterest_index / wp_pinterest_alts meta and reload each time—both clunky.

Two other pain points:
• Login relies on a saved Pinterest session cookie, not OAuth, so scheduled jobs die quietly whenever Pinterest forces a re-login (roughly monthly). Put a reminder on your calendar.
• The board selector is a single drop-down—multi-board pinning is possible, but only if you paste comma-separated board IDs by hand (undocumented). Advanced users can hook wp_pna_post_images to pull images from MetaBox/ACF fields, but that means writing a small MU-plugin.

None of these are deal-breakers, yet they turn what should be a set-and-forget solution into something that needs periodic babysitting. If your posts and images always share the same date folder, you’ll love it. If you work with back-dated media or expect truly hands-off automation, be prepared to tinker.