And breathe… the “file too large to send” problem is over

Authored by:

President

Jimmy Tran

Jimmy is a certified network and systems engineer with over 13 years of experience in building and managing IT infrastructure. He created LevelUp MSP to bring unique solutions to the world of IT service providers for small and medium businesses by focusing on delivering proactive virtual CIO services.

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We’ve all been there. You’re drafting an urgent email, attaching a critical file, and then—bam. Outlook throws up the dreaded “file too large to send” error.

Well, Microsoft has finally decided to do something about it. A new update to Outlook promises to eliminate this hassle once and for all, making file sharing seamless. And for once, something that sounds too good to be true… actually is true.

How It Works

Microsoft is integrating Outlook with OneDrive, so when you hit the attachment size limit, Outlook won’t just block your email—it’ll offer a smarter solution. Instead of rejecting your file, it will automatically prompt you to upload it to OneDrive and share a secure link with your recipient. No more manually compressing files, resizing images, or scrambling for third-party file-sharing services that can pose security risks.

Who Gets It First?

Android users will see this feature roll out first, but don’t worry—everyone else won’t have to wait long. Microsoft has confirmed a broader rollout starting this month.

That means in just a few weeks, you’ll be able to send large files without jumping through hoops. Just attach, send, and move on with your day.

If your business relies on Microsoft 365 and you want to make sure you’re getting the most out of it—without the headaches—let’s talk. We help businesses like yours streamline workflows, improve security, and maximize productivity.

Want to know more? Get in touch today.

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