How to Send Large Files From BigPond Email Using OneDrive in Outlook

Try to attach a video of the school concert, a batch of high-resolution photos, or a signed contract to an email from your BigPond account, and Outlook usually stops you before the message even leaves the outbox. Most email providers cap attachments somewhere around 20-25MB, and BigPond mailboxes, which now run on Telstra's own mail servers, are no exception. It's a common moment of confusion: the file exists, the recipient is expecting it, and Outlook simply won't send it.

The fix isn't to compress the file into oblivion or split it into five separate emails. OneDrive lets you upload the file once and send a link instead of the file itself, so the size limit that trips up attachments never comes into play. It works the same way whether you're on a Mac or a Windows PC, and it gives you options, like view-only access or an expiry date, that a plain attachment never could.

This guide walks through the process end to end: getting the file into OneDrive, generating a link with the right permissions, adding it to an email in Outlook on Mac or Windows, and checking it actually works before you hit send. It also covers a separate issue that trips up a lot of BigPond users in Outlook, mail server settings that changed some years ago and still catch people out, plus when it's worth getting help rather than troubleshooting it yourself.

Key takeaways

• Outlook typically blocks attachments over roughly 20-25MB; sharing a OneDrive link instead removes that limit almost entirely.
• A free Microsoft account includes 5GB of OneDrive storage, which is enough for most one-off large file shares.
• Set link permissions deliberately, anyone with the link, a specific person, or view-only, rather than accepting the default.
• If BigPond email keeps failing to connect in Outlook, the usual cause is outdated server settings, not a broken account.
• Test a share link in a browser before sending it, especially for anything sensitive or time-critical.

Why BigPond email attachments fail in Outlook

Outlook applies its own attachment limit before a message ever reaches the recipient's mail server, usually somewhere around 20MB on desktop and a little more through the web version, though the exact figure depends on the account type and whether an administrator has changed it. BigPond mailboxes, which have run on Telstra's own Telstra Mail servers rather than the original BigPond infrastructure since 2016, apply a broadly similar limit on the receiving end. Neither limit is generous once you're dealing with a decent video clip, a folder of RAW photos, or a multi-page scanned document.

None of this is a fault with your file or your internet connection. It's simply how email was designed, for short messages, not large payloads. OneDrive large file sharing works around the limit by moving the file out of the email entirely: the file sits in your OneDrive storage, and the email just carries a link to it. If you're uploading a large file at home, keep in mind that most residential NBN plans have upload speeds well below their download speed, so a multi-gigabyte upload can take longer than downloading the same file would. That's normal, not a fault.

Step 1: Upload your file to OneDrive

The process is the same whether you're using a Mac or a Windows PC, since OneDrive runs through a web browser or a desktop app on both.

• Open OneDrive. Go to onedrive.live.com in a browser, or use the OneDrive app if it's already installed and signed in.
• Sign in with your Microsoft account. This is the Microsoft account linked to your OneDrive storage, it doesn't need to match your BigPond email address.
• Upload the file. Drag it into the browser window, or use the Upload button to select it from your computer. For a large file, leave the tab open until the upload finishes rather than closing the browser or putting the computer to sleep.

If you're on a Microsoft 365 plan with more than the free 5GB of storage, you'll have more headroom for large or frequent uploads; if you're on a free account, keep an eye on how much space is left before starting a big upload.

Step 2: Create and configure a share link

Once the file has finished uploading, the sharing options are where most of the useful control sits, it's worth pausing here rather than accepting the defaults.

• Select the file, then choose Share.
• Set who can access it. OneDrive lets you choose between anyone with the link, only people already with access, or a specific person by email address. For anything sensitive, restrict this rather than leaving it open to anyone.
• Choose view-only or editing. View-only is the safer default unless the recipient genuinely needs to change the file.
• Add an expiry date or password if you have Microsoft 365. These options aren't available on a free Microsoft account, but a Microsoft 365 subscription lets you set a link to expire, up to 180 days out, or require a password before it opens, useful for anything you don't want accessible indefinitely.
• Copy the link once you're happy with the settings.

Step 3: Add the link to your email in Outlook

On a Mac

• Open Outlook and start a new email as usual.
• Address it and write a short note explaining what the link is. Recipients are more likely to click a link when they know what to expect, for example: "Here's the file via OneDrive, click the link below to view or download it."
• Paste the link into the body of the email.

On Windows

• Open Outlook and select New Email.
• Add the recipient and a brief explanation, the same as on Mac.
• Paste the OneDrive link into the message body.

Some current versions of Outlook will also offer to upload a file to OneDrive automatically the moment you try to attach something too large, inserting the link for you. Whether you see this depends on your exact Outlook version and whether it's rolled out to your account yet, so don't rely on it being there, pasting the link manually, as above, always works.

Step 4: Test the link before you send it

Before the email goes anywhere, open the link yourself in a private or incognito browser window, ideally while signed out of your Microsoft account. This shows you what the recipient will actually see, if it asks you to sign in or request access, the permissions aren't set the way you intended, and it's worth going back to Step 2 to fix them before sending.

Once you're confident it works, send the email as normal.

Keeping shared files organised and secure

A few habits make OneDrive sharing safer and easier to manage over time:

• Use a dedicated folder for files you share often, rather than sharing individual files scattered across your OneDrive. It's easier to find what you shared with whom later.
• Revisit old share links periodically. A link doesn't expire on its own unless you've set it to, so a file shared six months ago may still be accessible unless you remove that access.
• Keep a separate backup of anything important. OneDrive is a sync and sharing tool, not a replacement for a proper backup, if a file matters, make sure a copy exists somewhere other than the folder you're sharing from.

If managing this across a whole team or business feels like more than you want to handle manually, that's really a cloud storage setup question rather than a one-off fix, and it's worth setting up properly once rather than repeating these steps for every new starter.

Fixing BigPond email connection problems in Outlook

A separate, unrelated problem catches out a lot of BigPond users in Outlook: the account won't connect at all, regardless of file size. This is almost always a server settings issue rather than a problem with the account itself.

Since 2016, BigPond mailboxes (addresses ending in bigpond.com, bigpond.net.au or telstra.com) have run on Telstra's own Telstra Mail infrastructure, not the original BigPond servers. If Outlook is still configured with an old bigpond.com server address, it won't connect, and this is the single most common cause of BigPond accounts failing in Outlook. The current settings are:

• Incoming server (IMAP): imap.telstra.com, port 993, SSL enabled
• Outgoing server (SMTP): smtp.telstra.com, port 465 with SSL (or port 587 with STARTTLS), with "outgoing server requires authentication" turned on

If your account has been reconnected recently or migrated to a new device, it's worth checking these settings even if email has been working until now, a Windows or Outlook update can occasionally reset custom server settings back to a default that no longer matches. For a business account relying on Microsoft 365 rather than a personal BigPond mailbox, the setup process is different again; our Microsoft 365 setup and migration service covers that separately.

When it's worth getting local IT help

Most of what's covered here is a one-off, five-minute job once you know the steps. It's worth arranging help instead when:

• Large file sharing is a recurring need across a household or team, not a one-off.
• You're setting up shared drives, permissions or a proper backup strategy for a small business rather than personal files.
• Email keeps disconnecting in Outlook after you've checked the server settings above.
• You're moving from a personal BigPond mailbox to a business Microsoft 365 setup and want it done correctly the first time.

For small businesses in Perth working through exactly this kind of email, file-sharing and cloud storage setup, our small business IT support in Perth team can set it up properly and explain what's been changed, rather than leaving you to reverse-engineer it later.