Note that this is assuming that you’re
connecting to an Internet mail service such as Gmail, Yahoo mail etc. –
if you’re using a mail system that’s on a local network such as a
corporate intranet, the upload speeds will usually be much faster.

• If it looks like it’s going to take too long to upload, try the next step, which can effectively reduce the upload time.

3. Reduce photo size if necessary

• If you’re not sending images that will be printed at some stage,
  it’s rarely necessary to send them as the original, full resolution
  versions.
• Even halving the photo dimensions will not usually reduce quality
  that much, and in many cases can even make photos look sharper (digital
  cameras frequently push the limits of their sensor resolution via
  interpolation when using the largest photo size modes).
• This will also significantly reduce the file size (and upload times)
  – you can reasonably expect files to be less than half of the original
  size (and up to 10 times smaller if the original was saved at too high a
  quality).

You’ll probably want to use some software that can do this automatically for multiple images:

Windows – A good option for batch photo resizing is Irfanview.
After installing, select “Batch conversion/rename” from the File menu.
There are a lot of options here, but all that needs to be done is select
the image files from the file browser in the top-right, then click on
“Add” to add them to the list of images to be processed (small note –
there appears to be a bug in Irfanview where the “Add” button might not
work when only a single file is selected. If this happens, you can
instead double-click on the file to add it to the list).

• Now click on the “Use advanced options” checkbox, and then the
  “Advanced” button beside it. This will open a dialog with even more
  options, however, all that needs to be selected here is the “Resize”
  checkbox, then in the “Set new size as percentage of original” boxes,
  put in 50% (it will use this for both width and height).
  
• Click OK in the Advanced settings to go back to the Batch Conversion
  window. Now, the only other option to point out here is “Output
  directory for result files”. This is where the newly resized images are
  placed, so change it if necessary. Now click “Start Batch” and your
  images will be converted.
  

Mac – You can easily resize images using the Preview tool, see here for details. Note that you can select “percent” instead of “pixels” to get more consistently resized images.

Chromebook – Batch image resize options are currently a bit more limited on Chromebooks, however you could try the Bulk Resize Photos free Chrome Store app.

4. Put all the images into a single file

If you have more than 5 or 6 photos to send, it’s going to be much
easier to send them as a single archived file (e.g. ZIP file).

To create file archives, we’re using 7-Zip (Windows) as it’s free and high performance, however there are many options available here.

After installing, simply select all of the files you want to add,
right-click on the group and “Add to archive..” (image above).  It will
create a single “.zip” file with all of your photos in it.

On Macs, selected the files then Control-click and select “Create Archive”. For Chromebooks, see here.

If you have previously resized the images, you may have two copies of
each photo (small and large), so check that you’re only selecting the
smaller versions when creating the archives.

5. Send the photos

Files can be sent as attachments within an email, but there are some
restrictions – it’s similar to the way that parcels & packages in
the postal system have a certain amount of capacity for items sent.

Due to physical limitations on storage space and network bandwidth,
email providers have upper limits on the maximum size of attachments
that can be sent and/or received. For the most popular mail services,
this is currently about 25MB per message, for both sending and receiving
attachments.

25MB is not all that generous in terms of photo and video files, but
at the same time, it becomes more difficult to handle large files when
they are embedded within emails. To solve this problem, most email
providers offer an alternative of uploading your large files to their
online storage services (e.g. Google Drive), and then place a link to
the file in the email when it has finished uploading.

Since
the files themselves are not actually being sent with the email (just
the link to the files is sent), this allows for much larger 100s of MB
files to be shared.

Gmail

• Start a new mail, and click on the paperclip icon to attach files.
  The
  attachment size limit for Gmail is 25MB, however, if your file is
  larger than this, it will ask you if you want to send it using Google
  Drive, where the file size can be up to 10GB (10000MB).
• If you’re sending using Google Drive, it will show you the files you
  have currently uploaded. So click on the “Upload” tab and select the
  file to upload again if necessary, and click on the blue “Upload” button
  below.

• You will need to leave the browser tab open in either case while
  uploading, however it will continue uploading in the background if you
  simply switch to another tab or window.
• When the upload is finished, if you are attaching the file with
  Google Drive, it may ask you if you want to share this file with the
  recipient. Clicking on the default option here, “Share & Send”
  should be ok in most cases, it means that the person you’re sending the
  file to can see that file on your Google Drive storage area, but not any
  other files you may have there (unless you previously shared them).
  
  In this case, the recipients don’t need a Gmail or Google account to see
  your attachment once it’s shared, in fact they just need the link in
  the email. Be aware that access to your file is just like a normal
  attachment or image link – if the email is forwarded again, other
  recipients can click on and access or download the file attachment from
  Google Drive.
• If you select “Send without sharing”, the recipient may have to go
  through a further step of requesting access to the file. This may be
  useful where you need to send a file link to a group of people, but you
  only want to grant access to someone if they then specifically request
  it after they click on the link. In this case, the recipient will need
  to login to a Google (but not necessarily Gmail) account in order to
  request access.

A slightly confusing new feature in Gmail is the ability to send
files stored on Google Drive as a standard “Attachment” instead of
“Drive Link” (see example below).

This Attachment option is largely pointless for files that are not
already on Google Drive, since you can just click the paperclip icon in
Gmail to upload attachments directly, however if you’re in the habit of
using Google Drive to store your files (for example, Chromebook users),
this might be a useful option, since normal attachments remain
permanently with the email they were sent with, whereas you might delete
some files on your Google Drive at some stage, which could prevent
shared files from being accessible at some stage in the future.

Outlook.com (aka Hotmail)

• Create a new email, then click on the “Insert” option from the menu
  at the top. If your total file size is less than 25MB, select “Files as
  attachments” and upload the file.
• If your files are greater than 25MB, it will prompt you to use
  OneDrive, which is Microsoft’s online storage service. It’s slightly
  less integrated with email compared to Google’s version, since one you
  arrive at the OneDrive page, you’ll need to select the file for
  uploading once again, so if you know the file is too big to be sent as
  an attachment, it’s better to select the “Share from OneDrive” option in
  Outlook when composing your mail.
• After uploading, the file will appear on the OneDrive page, however
  now you have to go back to your email in Outlook.com, and select
  “Insert” and “Share from OneDrive”. You can then select the file to send
  with the email.
  

Yahoo mail

• Although it was reported some time back that Yahoo had got rid of
  attachment limits in email, this isn’t exactly true. For files over
  25MB, you’re prompted to use Dropbox to store the file before sending
  the email.
• This works in much the same way as the Google and Microsoft online
  storage services – you can access the files later as a separate virtual
  drive or folder on your computer, but the recipient doesn’t necessarily
  need any login details to be able to open the files you send them in an
  email.

Alternatives to using email

The universal nature of email is still a huge feature compared to
other services – you don’t need to ask anyone what software or system
they’re on before sending files to them.

However many people find that dedicated file applications are a better
option when frequently sharing files with the same recipient or group.

• Social networks and photo sharing sites such as Facebook, Google+,
  Flickr, Picasa and Instagram. These sites will usually let you organise
  photos into albums, and set access permissions for different people.
  They tend to be better suited for sharing photos on a periodic, social
  basis, instead of sharing a lot of photos at once.
• Messaging services such as Skype can often transfer files, however
  this usually requires that the other user is online at the same time.
• Using online storage services such as Google Drive, Microsoft OneDrive, Apple iCloud Photo Sharing and Dropbox
  outside of email. These services are designed to make files easily
  accessible, and can be very efficient when each party is using them to
  the full extent (for example, downloading the client program on each
  service in order to add a remote folder to their system).

Image credits: Waterfall photo courtesy of Gareth Thomas (Creative Commons 2.0 BY-ND license).
Microsoft Outlook icon courtesy dAKirby309.