Let's Talk About Holiday Email Attachments

This time of year gets crazy with attachments. Hosts send large PDF invitations to their guests, families send update letters, and excited friends share their holiday photo activities as they occur.

Email often becomes an alternative because people don’t want to take the time to hand-address classy invites and cards or print photos. Also, if they are wise, they don’t want to post too much to their social media either.

I get that; however, while convenient, PDF invites, photos, and family update letters sent via email shouldn’t replace receiving a hand-addressed, unique invite or card via snail mail. Sending that hard copy is so much more thoughtful and fun, don’t you think?

Technology is incredible when appropriately used, as I say, “with knowledge, understanding, and courtesy.” I repeat that a lot around here. Unfortunately, technology often becomes a crutch without thought or courtesy to the other side, and to cater to what we are unwilling to do otherwise.

Practical Tips for Sending Large Attachments During the Holidays

Especially during the busy holiday season when inboxes are flooded and servers can be slower:

Use cloud storage links instead of direct attachments: Upload the file to a service like Google Drive, Dropbox, OneDrive, or iCloud, then share a link. This bypasses email size limits (typically 20–25 MB for most providers) and avoids clogging the recipient’s inbox. You can set the link to expire after a few weeks if privacy is a concern.
Compress files before attaching: Zip or compress large files/folders using built-in tools (right-click → Compress on Mac, or 7-Zip/WinRAR on Windows). This can significantly reduce size—often by 50–90% for photos, videos, or documents—making them easier to send without hitting limits.
Choose a dedicated large-file transfer service: Use free tools like WeTransfer for files up to several GB. The service generates a temporary download link you can paste into your email. Other comparable services offer holiday-friendly features like password protection and expiration dates.
Check and respect size limits upfront: Confirm both your and the recipient’s email provider limits (e.g., Gmail/Outlook: ~25 MB, Yahoo: 25 MB). If in doubt, ask the recipient first or split the file into multiple smaller emails to avoid bounces or delays during peak holiday traffic.
Send during off-peak hours and follow up: Avoid sending large emails during high-traffic times (evenings or weekends around holidays), especially if sending to a known business email account. Schedule for early morning or mid-week if possible. Always include a brief note in the email body explaining what’s attached/linked, and follow up to confirm receipt, as holiday inboxes get chaotic.

Are you an aggressive attacher?

When it comes to attachments, many just “attach” because that is what they want to do or what is convenient at that given moment. Easy-peasy. However, it is not very thoughtful, given that you don’t know the recipient’s storage or bandwidth limits.

Remember that not everyone has unlimited resources to handle the many attachments you can send simultaneously, just because it’s convenient for you. We cannot count on the other side, sitting at their computer, to download them immediately and keep their inbox flowing. This is why it is courteous to ask first when the best time is to send multiple photos or large attachments.

Email is not for huge attachments.

Your camera creates mega-megabyte images. All you have to do is take a moment to resize each image to no more than 1000 pixels in width before sending it. Then, if you want to send a bunch of files, zip them up.

By being aware of these small issues, you will show an understanding of the technology you are using (tech-savvy) and consideration for those you communicate with. Plus, you won’t have to worry about inconveniencing the recipient with limited storage, bandwidth, or service.

Why not brush up on attachment dos and don’ts with my article “Don’t Attach That!” while you are at it?