Sending messages from webpage to extension

I'm building a niche extension that should work in tandem with my nextjs web app. I already have a content script working with Plasmo so I maybe could injects some buttons into the page, but since I have control of the web app also it seems better to be able to build my own buttons there but have them only display if the extension is installed and when clicked, send a message to the background worker. I've tried using the plasmo/messaging package from the web app (doesn't seem to work) and I've tried the chrome.runtime.sendMessage API, but with inconsisent results. Is this becuase plasmo's dev server is not loading properly or am I doing something else wrong?
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