How to send large files through Outlook 365 webmail

Even today, popular email services like Gmail and Outlook 365 don’t allow you to send large files. While this is usually not allowed for fear of wiping the recipient’s mailbox, the 33MB file size limit for Outlook webmail users can sometimes be a bit of a problem.


Send large files through Outlook 365

Nowadays, the problem is more real because even simple photos take up a few MB. And if you attach a few, you easily run out of space. And the same can be said about video files. So what do you do in situations like this?

Well, don’t give up all hope. There are some nifty ways that can help you transfer large files through Outlook 365. In this article, we will see some of the best.

Let’s go.

1. As a OneDrive link

Most of us often have the habit of dragging and dropping our files into the mail window. If the files exceed the size, you will see a warning image appear at the top of the email window. However, try to download it through the attachment icon and you will see the option to download it as a OneDrive link.


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All you have to do is download the file, choose the OneDrive option, and it will download soon. The default setting is that anyone with access can edit the file.

To change the settings, click the little icon at the bottom and choose Manage Access. Then select one of the two options – Anyone Can Edit or Anyone Can See.


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At the same time, go to your OneDrive’s shared folder if you want to set an expiration date.

2. As a Google Drive link

While OneDrive is native to most Outlook users, Office 365 users can also try Google Drive integration. Similar to OneDrive, you can share file links directly from Google Drive.

One of the easiest ways to add Google Drive to Outlook webmail is through Settings. Click on it and choose Show All Outlook Settings> Attachments. Now click on the Google Drive icon.


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You must provide username, password and authorization. Once done, all you need to do is tap on the attachment icon> Choose cloud location and select Google Drive from the menu on the left.


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Then choose the files you want to attach, and that’s about it.

Nice tip: Similar to OneDrive shared files, you can also set the visibility of the attached document.

You can also add your Dropbox account if you have one. If you use all of these cloud storage solutions, you can add them all. And whenever you need to send large files through Outlook, just choose the appropriate storage solution from the left panel.

What makes these two methods super useful is that you can remove them at any time. Go to Settings> Show all Outlook settings> Attachments, then press the Remove account button.

3. Firefox Send (files up to 2.5 GB)

Firefox Send officially debuted in March 2019, and the best part is that it’s supported on all major platforms. In addition, it is free.

By default, you can send files up to 1 GB. However, if you use your Firefox account to sign in, you can send files up to 2.5 GB.


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What I like about Firefox Send is its simplicity. You just need to drag and drop the files into the window. You can choose the number of downloads or the expiration date of the file link. Moreover, you can also choose to protect the files with a password.


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And as mentioned above, Firefox Send is also available as Android and iOS apps. So if the file is on your phone, you can download it directly from there and share the link through Outlook 365 webmail.

Yes, no worries to send the file to your system and then download it through Firefox Send. Once done, share the link with your recipient and that’s about it.

4. WeTransfer

WeTransfer is another file transfer service like Firefox Send. This allows you to send files up to 2 GB. And unlike Firefox Send, you don’t need to add the links and then send the email separately.


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Here you can add the files, add the destination and from address, the message and download it. The mail with the file and the message will reach the recipient soon. The only problem is that the email will be sent from We Transfer, increasing the chances of the email landing in the Spam folder.

A workaround is to send the email to your mailbox and then add the link in the compose window of Outlook 365. A bit long, but doable process.

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5. Send Zip files in multiple parts

If you have multiple files that are a few GB in size, you can split them and then compress them. Tools like 7-Zip easily come to the rescue in situations like this. All you have to do is remember to name the folders correctly.


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Once done, send them in separate emails and you’re good to go. And with the new version of Outlook, it’s pretty easy to spot attachments in a thread. Click the attachment icon at the top of the thread, which will display a drop-down list of all attachments in the conversation.


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Select a file to open or download. Yes, absolutely no way to open the discussion thread or the conversation.

Get, Set, Go!

I especially like using Google Drive to send large attachments, be it a bunch of images or a video file. Best of all, it syncs across all of your devices, making it easier to find and join files.

Which method do you prefer?

Next step: Are you using Outlook on iOS? If so, read our compilation of the best and best Outlook tips and tricks for iOS to use it like a pro.

Last updated on May 17, 2019


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