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 Mar 8, 2021 4:32 PM

Lotus9999 wrote:

There's a similar thread also, which has double the number of pages of this one:

https://discussions.apple.com/thread/251807601

There only seems to be 2 solutions to it:

ONE: I've done some testing now Sending pictures using Outlook app, and here are my findings:

1 - If you start in the Outlook app and attach pictures, they will still show up EMBEDDED. …

Actually, just as with Apple Mail, I expect that they are just as much attachments! (I wouldn’t be inclined to think otherwise, unless such was demonstrated to be otherwise upon inspecting the Raw email text.)


However, this does seem to demonstrate that Outlook, as well, is able to format emails as rich-text (text/html, actually). (When I worked within the corporate/governmental sectors, I would only send emails as plain-text if the other party had requested such, or I was replying to a plain-text email.)


I suspect, however, that if you sent this email to an email address where you use Outlook to read the email, that Outlook would allow you to perform bulk attachment operations (such as bulk-saves).


If not, I would actually be surprised! However, in that case y’all could use that as the best leverage to have Microsoft (at least partially) fix Outlook, and its derivatives.


… 2 - However, if you start in Photos (as others I believe have indicated), then choose the method to share as the Outlook app, they DO in fact show up as attachments! And there's no need to attach a 1 second video...

Yes. This should surprise no one.


Of course, as always, the real test is not in the appearances, but in the functionality: does Outlook (or another email client) allow you to perform bulk attachment operations (such as bulk-saves)?


… The only downside is that unlike when sending pictures by Mail, where you get the option to choose the size of the photo (S/M/L/Original), there are no options and they are sent as full-size by default.

Meh …


… Based on this solution, perhaps any other third-party app on the iPhone can be used with similar results, and not just the Outlook app. …

Make sure y’all don’t get caught up in the appearance, but pay attention to the functionality: does Outlook (or another email client) allow you to perform bulk attachment operations (such as bulk-saves), regardless of appearance?


… TWO: The other one allows you to still use the default Mail app, and by attaching a different file (such as a 1 second video), it forces it to send all of the pictures as attachments also.

As always, «the pictures» are sent «as attachments», always.


The only potential differences are:

  1. In the appearance of the email, and
  2. Whether Outlook (or one of its derivatives) will allow you to perform bulk attachment operations (such as bulk-saves), regardless of appearance.
292 replies

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.

May 13, 2021 11:45 AM in response to deane160

I found a workaround, but take it with a grain of salt.

I asked some friends to send me some test pictures using different OS (Win, Linux, Android) and all came in as attachments except iOS 14.


Solution;

Make a random blank file (pdf, note, 15 sec video) and name it "iOSFluxCapacitor" or "iOSDiscombabulator" ... :-) or whatever you want.

Adding the file with the image (s) will force the email system to attach, not embed, all the files including the image (s).


NOTE: Hope this work for you guys. I know my life is a whole lot better now that I don't have to download each image one at the time, but all at once.

Nov 1, 2020 11:18 AM in response to Cwills1995

I’ve kept with this thread for a hot minute. I saw there was a 14.1 IOS update and crossed my fingers that would solve the issue but of course it did not.

However, I found that if you go to your Pictures app, select a picture, go to more options, in the list of apps to choose from you can pick Outlook and that makes the picture an attachment not embedded. (Not sure if you were able to do that before 14.1 or not but this find will help my users at my company for the time being) **Though going to Outlook first and attaching an image from in the app still has it embedded.

I hope Apple will wake up and make an actual fix for this issue all around. It’s ridiculous

Jan 27, 2021 10:58 AM in response to Shajk2020

despite the absolute ridiculousness of this and the BS excuses they are providing, i have found that, like some of these other people, if you attach something else, like a PDF or other document to the email before sending, it then sends them all as an attachment rather than in line. Test it to yourself and see what works. thats the only work around that I've found to work (most) of the time.

Apr 3, 2021 10:53 AM in response to jhaight

jhaight wrote:

Settings
1. …
I think this changes the file from HEIC to JPG …

Yes. That is what those settings change.


However, it’s not like the HEIC is some proprietary format. It is an International standard. Unfortunately, some software require their users to make additional purchases, in order to work with this newer and superior format.


… and somehow that solved the problem. …

I’m glad this helped solve your particular issues.


Unfortunately, this change is not sufficient for the issues others have been experiencing. (The difference has to do with the email client used at the receiving end.)


… Hope this works for others having this problem.

Thank you for your contribution!

Oct 8, 2020 1:28 PM in response to deane160

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

Jan 9, 2021 11:35 AM in response to Supportmenot-elppa

THAT SOLUTION WORKS, krwakefield! On my iPhone I made a 3 second video that I will attach with my photos when emailing them to myself. The resulting email does have photos show up in my Outlook email account as JPG files. APPLE, PLEASE FIX THIS! WE WANT EMAILS SENT FROM OUR IPHONES TO HAVE PHOTOS AS JPG ATTACHMENTS (NOT EMBEDDED) EVEN IF THERE IS NO VIDEO OR PDF ATTACHED.

Feb 26, 2021 12:47 PM in response to Lotus9999

I use Gmail by default on my iPhone 7 version 14.4. When I try to attach a photo it ends up embedded inline in the text. But if I tap on the photo I get a 'Send as attachment or Remove' pop-up option. Selecting 'Send as attachment' reduces the photo to an attachment sized mini photo at the bottom of the test page. Problem solved but this only works in Gmail. It doesn't work in Apple's own Mail app!

Mar 4, 2021 10:49 PM in response to Halliday

I started this thread/question way back in Sept and so I have received and read all of the many replies and so far only the one solution has worked for me and it’s not a perfect solution. I have an iPhone 12 plus and use gmail and outlook for my personal and work emails. The only way I’ve found to be able to send photos from my phone via email so that they are attached to the email as JPEG’s and not embedded in the email is to attach a saved document from my phone and send it together with the photos. So I can still only send to myself as I then need to go to my computer and resend the email to whoever I want but obviously delete the doc attachment that I sent. Bloody annoying but 1st world problems hey!

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.)

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Emailing photo attachments from my iPhone 11

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