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Re-Uploading a File With the Same Name Doesn’t Replace It

Field Note #127
🔬 Resolved 🟢 Beginner ⏱ 5 Minutes ✓ Observation from Experience

⚡ Quick Fix (TL;DR)

The Fix: Don't upload a fresh copy to replace an existing file. Instead, open the existing Media Library item and use Replace Media (built into recent WordPress core versions, or available via a plugin like Enable Media Replace if your version doesn't show it). That swaps the actual file contents while keeping the same filename and URL — no code changes needed anywhere else on the site.
After replacing, clear caches in the usual order (build/optimization plugin cache → page cache plugin → any server or CDN-level cache) and hard-refresh, since a stale cache can still serve the old bytes even after the file itself has correctly been swapped.

Was this helpful? Thanks for the feedback!
You fix an image, upload it again under the exact same filename to swap out the broken version, hard-refresh the page — and the old, broken version is still there. You clear every cache you can find. Still there.
At this point it’s tempting to assume it’s a caching problem. Sometimes it genuinely is. But there’s a simpler explanation worth ruling out first.

What’s actually happening
WordPress’s Media Library does not overwrite a file when you upload something with an identical filename. By default, uploading my-image.webp a second time creates my-image-1.webp alongside the original — the URL your page actually references (…/my-image.webp) keeps pointing at whatever was uploaded there first. Every “fix” since then may have been sitting unused in the Media Library under a different filename the whole time.

How to tell the difference
Search the Media Library for the base filename (without the extension). If you see -1, -2, -3 versions stacking up, that confirms it — none of the re-uploads have actually gone live under the original URL.

The fix
Don’t upload a fresh copy to replace an existing file. Instead, open the existing Media Library item and use Replace Media (built into recent WordPress core versions, or available via a plugin like Enable Media Replace if your version doesn’t show it). That swaps the actual file contents while keeping the same filename and URL — no code changes needed anywhere else on the site.
After replacing, clear caches in the usual order (build/optimization plugin cache → page cache plugin → any server or CDN-level cache) and hard-refresh, since a stale cache can still serve the old bytes even after the file itself has correctly been swapped.

How to avoid it next time
Whenever you’re updating an existing image (not adding a new one), go looking for a “Replace” action first, rather than the default upload button. It’s a one-click habit that avoids an entire category of “why isn’t my fix showing up” troubleshooting.

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