A group of Microsoft Products and technologies used for sharing and managing content, knowledge, and applications.
Hi @Seth Dunn,
I hope you’re having a great day. I’d like to share a bit of information I’m aware of that may provide some context for your question.
What’s happening here is usually related to how SharePoint’s sharing dialog works behind the scenes. When you type an email address into the “Share” box, SharePoint uses the People Picker to try to resolve that address against your organization’s directory. If the Gmail address you enter happens to match, or closely resemble, an internal user, an alias, or even an identity that was previously associated with your tenant or the site, SharePoint may automatically switch it to the internal company email.
A reliable workaround is to copy the SharePoint item link first, then paste that link into a separate email using Outlook, Gmail, or another email client. Send the message directly to the external recipient without using the built‑in SharePoint sharing email field. As long as the link permissions are configured correctly (for example, using “Anyone with the link can edit” or the appropriate site‑specific sharing option), external users will still be able to upload files successfully, and you’ll avoid autocomplete or identity‑matching issues altogether.
One additional thing to double‑check is that external sharing is enabled both at the organization level and at the SharePoint site level, as restrictive settings can sometimes affect how the sharing experience behaves.
I hope this helps and works smoothly for your scenario. Thanks again for posting your question
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