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Emailing photo attachments from my iPhone 11

Since the ios14 update when I now email photos from my iPhone using either my work outlook or personal GMAIL addresses they are now sent embedded in the email message and not as jpeg attachments to the email. Why is this and how do I fix it or what settings can be changed, if any?

Posted on Sep 23, 2020 7:23 PM

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Posted on Oct 8, 2020 1:28 PM

Okay I figured out a fix to this since we can't get a useful response from the Specialists. As a heads up, this was through Outlook, not Gmail, but I am assuming the process would be the same/similar.


  1. Open the email with the embedded photos.
  2. Click File -> Save As.
  3. Choose the folder where you want the photo files to be saved.
  4. Change the "Save as type" in the bottom dropdown box from "Outlook Message Format - Unicode" to "HTML".
  5. Save file.


There will be a couple of extra random files that won't be used, but a folder with all of the photo files will now appear in the folder you selected to save the email to!


Hope this helps

292 replies

Mar 17, 2021 10:54 AM in response to Skeptical66

Yes, Skeptical66, that seems to relate to the Content-Type being used, as per N-K-O’s investigation. (My response to N-K-O’s investigation can be found at https://discussions.apple.com/thread/251807601?answerId=254616832022#254616832022.)


A far better way to judge correctly, as to what is going one, such as “embedding” vs. “attaching”, or other changes that affect the very tiny subset of email clients that prevent users from performing bulk attachment operations (such as bulk-saves) based only upon some set of variations within the internal features of an email, is to use the test found in my comment at https://discussions.apple.com/thread/251807601?answerId=254806789022#254806789022.


In fact, now that we have such a definitive test, I don’t believe we should make claims without backing them up with that test.

Mar 18, 2021 3:13 PM in response to euro37

Welcome, euro37, to Apple Support Communities!


And what email client is being used on the email receiving end?


There is no such thing as «“embed picture”», all are always «“sen[t] as attachment[s]”».


You don’t need to believe me. You can check for yourself by performing the definitive test found in my comment at https://discussions.apple.com/thread/251807601?answerId=254806789022#254806789022.

Apr 23, 2021 4:03 AM in response to VenomInMyVein

VenomInMyVein wrote:

add also another type of file, like a pdf oder something to the mail and it will send the pictures as an attachment.
this is not a solution, but it works as a work-around.

Yes. This is a workaround that modifies the sort of attachment structure, used by the email, is within the more stilted and limited attachment structure the very tiny subset of email clients (consisting of a single email client and its derivatives) actually seems to recognize.


No other email clients have this limitation.


You don’t need to believe me. You can check for yourself by performing the definitive test found in my comment at https://discussions.apple.com/thread/251807601?answerId=254806789022#254806789022.

Dec 1, 2020 12:51 PM in response to deane160

Hey All!


I seem to have found a fix for this, I am not sure if it will work for everyone but it did for me. This seemed to happen since Apple changed the way that photos were saved after taking them with the camera from JPEG to HEIF/HEVC. If you follow the steps below, it will save future photos as JPEGs, and I have observed them acting the way they used to, such as emailing as attachments. Please try the following:


  1. Open Settings > Camera (it is relatively far down on the list)
  2. Tap Formats
  3. Switch from "High Efficiency" to "Most Compatible"


This will save future photos you take as JPEGs, but It should not convert already taken photos.


Please note that in cases where you require extremely high quality videos and photos, it may not let you use the Most Compatible option.


I hope this helps! I am no expert but I found this out and I hope it helps others like it did for me.

Dec 1, 2020 1:53 PM in response to deane160

Yeah! I actually came back because I learned something else, it is not enough to turn on compatible. This actually may or may not be the solution, but I also had it to where it would embed into the email just now.


The way I could replicate it sending as an attachment is actually HOW I was sending the email, not the compatibility mode. In order to get it to send as an attachment:


  1. Open your Mail app and compose an email as if you were sending a normal email
  2. Tap anywhere in the body of the email to bring up predictive text
  3. Tap on the arrow on the far right of predictive text
  4. Click on the photo icon (not the camera) and choose the photo(s) you want to send
  5. Send the email


This actually worked to where it sent as an attachment every time. I had compatibility on though, so I am unsure if it is a combination of these that created the solution.

Dec 5, 2020 8:07 PM in response to iW00

Thank you, iW00.


To @All:


For iOS (and iPadOS), there simply was no change in attachments’ options, since regardless how any particular email client may choose to display (render) any given email, files are always attached to the email: this is a very old part of the email Internet standard, and is highly unlikely to change in the foreseeable future.


The only problems are:

  1. An apparent change in the interaction between Apple Mail vs. Microsoft Exchange servers over the Simple Mail Transfer Protocol (SMTP): if the transfer of email uses just about any other route, the “issue” seems to be avoided.
  2. An apparent change in the default formatting of authored emails in Apple Mail. However, there has been, absolutely, no change in the way files are attached to such emails.
  3. The simple fact that Microsoft Outlook prevents users from performing bulk operations on attachments (such as bulk-saves), purely based upon the way Outlook chooses to format (render) a received email: no other email client seems to have this problem!


The first item, if there was an actual change in the SMTP, it would have only been in accordance with the SMTP Internet standard, which gets updated, now and then, and, unlike Microsoft, Apple, and others, tend to stay current with such standards.


Eventually, Microsoft will “get with the program”, as they usually do, even though they tend to “drag their feet”.


The third item will only be fixed if people properly complain to Microsoft, about how Outlook is improperly interfering in their use of email attachments.


The second item is the only one that y’all may be able to talk Apple into changing: they could provide an option to change the default email authoring format to the (very old and “dying”) plain-text format.


Be aware that the old plain-text email format was going “extinct” even back in the ‘90s!


Likewise, due to the issues with Microsoft software, there is simply no guarantee that such a change will actually solve the Outlook issue. It might, but there’s simply no guarantee.


The single guaranteed solution is for Microsoft to fix Outlook, so it permits you, the user, to perform bulk attachment operations (such as bulk-saves) on any received email, regardless how Outlook chooses to display (render) said email.


(The only affect that the plain-text format has on email attachments, is that there is no way to render [display] email attachments “inline” with the email text, since it cannot contain any formatting, whatsoever.)

Jan 14, 2021 5:48 AM in response to sterling r

I guess I've found the solution. Maybe it's been stated herein already. If so, my apologies. If not, looks like you have to email yourself the embedded image. Then:


  1. open the applicable email
  2. right click on the photo
  3. choose "Save as Picture"
  4. Name and Save


I'm on Windows 10 and using Outlook. I've only tried this from the laptop, not from the phone. This is the problem with Apple and it's always been this way (had my first MacIntosh in the late 1980s): forcing us to do business the way they want us to do business rather than allowing us to do business in the most efficient manner for ourselves.

Mar 8, 2021 5:02 PM in response to Pvjoy

That is but the superficial and circumstantial assessment, Pvjoy.


There’s a reason why circumstantial evidence is not admissible within courts of Law: such is often misleading.


Those of us, here on Apple Support Communities, that actually took the time (a month or two, starting in September) to understand the root causes if this issue are all in agreement:

The answer, as I, and others, have posted for months, here and within previous Discussions on this issue, are twofold:

  1. Apple Mail is, and always has been, «send[ing] emails … where the photos are … attachments, like how it [has always] be[en] for years», even at those times, through the years, when this Outlook issue surfaced with previous iOS versions.
  2. As far as getting your Outlook (and Outlook derived) email clients to allow you, the user, to perform bulk attachment operations (such as bulk-saves), that is not something Apple can actually fix. Y’all must contact the responsible company, in order to have that fixed.
  3. Anything else is but a fragile workaround, subject to being easily broken by any tiny changes in the web of interactions involved in transferring emails. (This is how this issue came up with the change to iOS 14, as well as many other times, in the past years, with earlier iOS versions.)

Apr 3, 2021 10:05 AM in response to deane160

I was having the same problem when trying to send a photo I took with my new iPhone 12 Pro Max. I'm not in the least bit savvy about these things and the person I was sending it to came across this. Here's what we did to make it work.

  1. Settings
  2. Open Camera (found in the 6th block down the lists)
  3. Formats
  4. Choose "Most Compatible"

I think this changes the file from HEIC to JPG and somehow that solved the problem.

Hope this works for others having this problem.


Nov 21, 2020 3:34 AM in response to rmjohnson144

Open the photo app, click on select, then slide your finger across all the photos you want to send (share), if you just want to send one photo, just click on one photo, then click the share button, then click on the email button.

if you want to copy a pic, then paste it in an email, you have to scroll down after clicking the share button, (the box with the arrow sticking out the top.) there are multiple options to choose from when scrolling down. See last pic




Dec 17, 2020 2:39 AM in response to Halliday

i just tried emailing photos using the iphone mail app to my gmail and yahoo account, and both display embedded images, not attachments. Below is a screenshot of what i get. So, again, how is this this not a Apple update issue? We used to get images as little thumbnail attachments, then apple performed update 14.2, and now we have all these complaints.




Oct 2, 2020 2:10 PM in response to deane160

Hello deane160,


We're glad you had the opportunity to update to the latest iOS. We do want to advise that this may be expected when attaching a photo in an email. To clarify a bit further, when attaching a photo are you presented the option to choose a size for the photo to attach, and does it appear in the body of the message? If so, this is expected.


Have a great day!

Oct 2, 2020 3:40 PM in response to Todd0213

Hi, yes when I email a photo from my iPhone which is often for work, it does give me a size option to choose before sending and I normally choose the mid size. It does not give me any other options though such as to choose if embedded or attached to an email. I have had an iPhone since the beginning, iPhone 3 and I have not ever had this issue before, photos were always sent as attachments to the email which is what you would expect. I don’t quite know who would ever actually want photos sent embedded in an email. This issue has only occurred now since the iOS14 update so please ask the powers to be to fix. Everyone is telling me to change to Samsung which I’d just rather not do. Thanks.

Emailing photo attachments from my iPhone 11

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