In the latest iOS patch from Apple, iOS devices running 14.2 are no longer able to send pictures as attachments. Instead, the image a user attaches are embedded into the body of the email, not as a separate attachment.

While considered a minor inconvenience for some, this undocumented change to attachment processing had a more significant impact to those that are required to operate without the use of HTML, as image embedding is only possible with HTML. With “plain text only” emails enforced in a workplace, images will not load or in some cases will output a content error within your mail application.

One workaround to send pictures as attachments not as embedded images would be to use the Microsoft Outlook App for iOS. The app is free to download, does not require any Microsoft subscriptions for its use and can support mailboxes hosted in Microsoft Exchange, Office 365,, Gmail, Yahoo Mail, and iCloud. This alternative mail app from Microsoft offers all the mail management functions as the native iOS mail app, except it still attaches images as attachments, not embed them.

Alternatively, a long-winded workaround discovered on the Apple user forums is; to send a text message to an email account. Doing so allows the addition of images as attachments, which are then offered to the recipient as attachments as expected or if there are multiple images, they’ll get uploaded to iCloud for you as the sender. The recipient will be offered a download of all of the pictures in the form of a .zip file.

So far, there has been no official statement or even acknowledgement from Apple regarding this change that has left many users frustrated.

If you’re having issues this, other email-related problems or have any questions regarding email security, please let us know, and we’ll do our best to assist. For what we do today, secures your business for tomorrow.