How To Email Multiple Photos Without It Failing To Send

I regularly get messages along the lines of, “apologies for the 6 separate emails but the pictures wouldn’t send all together,” or “my emails won’t attach all the photos, I don’t know how to get them to you”. Sound familiar? If so, this post is for you. Today I’m going to reveal how to email multiple photos without it failing to send. Hurrah.

There are a few ways you can improve the chances of your email sending when it has several image attachments. Please note that I’ve written this article with my blog’s contributors foremost in mind; fine tune image sizes & other details accordingly for your particular email client/recipient.

How To Email Multiple Photos Without It Failing To Send

Resize The Images Before Attaching

A lot of the time I get sent emails with image attachments which are full size – and they really don’t need to be. This is the case for photographs in particular, whether taken with a camera or a mobile device.

Digital photographs, in their raw state, have bloody massive file sizes. Even without looking at the actual file size in MB, the literal size of the photo in pixels is big enough. Raw photos I receive by email are often between 1600 and 4000 pixels longest side (huge!).

When you consider that I generally resize them so they’re 600 pixels longest side before uploading to my blog, they’re pretty damn big at the point of reception.

Image Resizer For Windows

You don’t need any fancy-schmancy design programs on your PC in order to fix this. There’s a free tool called Image Resizer For Windows which adds an option to your right-click menu.

How To Email Multiple Photos Without It Failing To Send

Once you’ve installed it, simply select all the images you’d like to resize in the folder, right click and select ‘resize images’. A box will appear giving you various options. If you’re sending photos to me as part of a Spotlight feature or with a Pleasure Panel review, it might be helpful to know I upload images which are 600 pixels longest side.

Take note of the options for whether you’d like to replace the original files or create resized copies (which will retain your original, full size images as well as creating the smaller sized copies).

Multiple smaller sized photos can then be attached to an email and has more chance of sending successfully.

‘Zip’ The Images Into A Zipped File

With email data sending restrictions on the increase across many mail servers, you may find that the above photo resizing tip still doesn’t completely solve the problem.

Did you know you can select multiple files in a folder, right-click and select to zip the selected files into a zipped folder?

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Doing this compresses size of the selected files – temporarily – like squishing them all into a vacuum-seal bag. The zipped (and therefore smaller sized file than if you were to attach all the files individually) folder is then attached to an email, sent to the recipient and hopefully delivered successfully.

The recipient receives the email with the zipped file attachment, downloads it and ‘unpacks’ it. This is usually as simple as clicking on the downloaded file, viewing the contents and moving them to a local folder – the process of which restores the files to their full-sized state.

Nifty, huh?

Use A Third Party Sending Program

Email with attachments still not sending? Hmm. Sometimes, no matter what you do, you just can’t get that email to send. It may be that you just *have* to send large sized files, or you’d like to send a movie clip (video files tend to be enormous) or you have wa-hey too many image files to resize/zip and send successfully.

There are third party image senders on the web – you don’t have to resort to options like trying to send images via social media private messaging (Facebook in particular has a habit of automatically reducing the quality of images sent between users).

Using WeTransfer

How To Email Multiple Photos Without It Failing To Send

My usual go-to is WeTransfer. Now, WeTransfer has a habit of making you think you have to pay to use it – don’t fall for it. I find it easiest to use and understand the desktop website, which has a ‘take me to Free’ option from the start.  Then, on the left hand side of the screen you have to agree to the terms and conditions before you continue.

You can send up to 2GB to an email recipient (or multiple email recipients) with the free level of WeTransfer. Click the + button to add files, then fill in the recipient details, add a message if you wish (so they know who it’s from!) and click transfer.

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Your files will be delivered to the recipient(s), in the form of a download link in an email to them from WeTransfer.

How To Email Multiple Photos Without It Failing To Send

There are various other options with WeTransfer but you’ll find many of them are there to tempt you to upgrade to the Pro version. I find the free level is good enough for my infrequent needs.


I hope this guide has given you some helpful tips about how to email multiple photos. If you still have issues, feel free to comment below or email.

How To Email Multiple Photos Without It Failing To Send

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How To Email Multiple Photos Without It Failing To Send

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