How Claude connectors silently fail

In engineering, there is this concept of a “silent failure”.

Silent failures are errors in a system that never get surfaced properly. In software this happens easily if you are not careful, and it makes root-causing an outage extremely difficult.

In some ways they are the worst kind of failure, because you cannot observe them.

In our experience rolling out AI, the biggest category of silent failures we have seen comes from installing Anthropic’s official marketplace Claude connectors.

Silent failure modes

Gmail. We run into this one all the time. Google’s official Gmail connector has nothing that allows Claude to see the attachments in your email threads. So when Claude says it has read the thread you have with a client, it has only read the text. It did not read any of the creatives, designs or drawings that were sent as attachments.

Google Drive. Despite it not being documented, downloading a file from Google Drive fails for large files, because the connector faces the same limits as the APIs it is built on. And when creating files, it requires all content to be base64 encoded.

With the 20k character limit, that essentially rules out creating large files, or any file with an image in it. You also cannot edit files, only create them. And the connector gives you no access to suggested edits, so AI cannot see any redlines.

All of these limitations, and plenty more, make the Google Drive connectors far more limited than most people realize.

Closing

The truth is that most of these companies are not incentivized to build the best connectors. Google wants you to use Gemini. Microsoft wants you to use Copilot.

The good news is that it is not that hard to build custom ones. We have built custom Gmail connectors that let customers search more than nine years of client communications.