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

Oct 19, 2020 8:21 PM in response to deane160

For everyone out there i have had a long chat with a very rude customer services rep named Meranda, from apple who first of all told me the removal of the ability to send an email with an attachment was “expected behaviour” as a result of the 14.0 update.


She then tried to blame the different email servers, she then back tracked and said it was a surprise to apple that it had happened and then variously tried to blame the email providers and back to the “expected behaviour” story.


She admitted that there was no warning that this functionality would be removed in the update information provided by apple and that an update couldn’t be reversed, thus not giving anyone the chance to realise the update may not be for them because it would have a seriously negative effect on the way they work.


In my case it has rendered my iPad Pro, apple pen an iPad 11 useless for the purpose I have been using them in my business for the last four years and all of them are less than a year old. I have no viable alternative to jump onto so its going to cost me loss of business, I’m sure I’m not the only one. It has also cost me a great deal of lost time finding out it wasnt an error pin my part.


The best she could tell me to do was to put a request in feedback.


She had clearly been briefed to lie, befuddle and fob off people such as myself who I have discovered this very serious removal of functionality.


I hope this is useful info to anyone before its removed by Apple, as two previous posts have mysteriously disappeared from here.



Dec 7, 2020 9:42 AM in response to Chucklepvfc

Chucklepvfc:


Internet standards keep evolving.


In fact, there was a new, official Internet protocol standard this month!


Some companies, like Apple, and others, keep up with the Internet protocol standards, some, whose name shall not be mentioned, “drag their feet” in coming into compliance with new standards.


Additionally, the Internet protocol standards for email are designed for human-to-human communication, which may not, necessarily, align with the use-case of trying to use email to transfer images/pictures to other computer systems.


However, that being said, none of y’all would be having these issues if it were not for the way Microsoft Outlook disallows bulk attachment operations (such as bulk-saves) based solely upon how Outlook chooses to display (render) your received emails!


As far as any of us has seen, so far, Microsoft Outlook is the only email client that misbehaves in this manner.


Unfortunately, Apple has no control over Microsoft’s products.

Dec 7, 2020 11:35 AM in response to TPITTS437

Operating System upgrades are, typically, the places where implementations of new Internet protocol standards are introduced, TPITTS437.


Sure. There was a change in either the default way Apple Mail formats authored emails, or in the implementation of a newer version of the Simple Mail Transfer Protocol (SMTP) Internet standard used to transfer email from Apple Mail to your chosen SMTP email server (going to a Microsoft Exchange email server seems to be the only troublesome link, here), or both; that seems to have triggered the issue that already existed in Microsoft Outlook.


As for attachments, to emails, they are still attachments! That hasn’t changed.


The only problem is that Microsoft Outlook prevents you, the user, from performing bulk attachment operations (such as bulk-saves) based solely upon the way Outlook chooses to display (render) your received email.


So far, none of us have seen any other email client that misbehaves, in this way.


This, and the various workarounds, simply emphasize the fragile nature of any means of trying to get Microsoft Outlook to “do the right thing”™️.


Such will continue to be fragile (subject to being easily broken), until Microsoft fixes this misbehavior in their Outlook software.


Unfortunately, Microsoft is highly unlikely to fix this issue, unless y’all let them know that this misbehavior causes you difficulty.


Y’all are also encouraged to provide Feedback to Apple, but anything they may do will remain fragile, until Microsoft Outlook has this issue corrected.

Dec 8, 2020 11:34 AM in response to SawyerTX

This is the problem!

Every time I send or receive an embeded photo in the body of the email, I have to left click to select the photo. Then right click to "save photo as..." THEN, I have to go find the file I want to save it in. (which for me can very extensive file paths due to my organizational and compartmentalized philosophy) I have to follow the same procedure for every photo.

My best work-around is to just plug my phone into my PC using the lightning cable, then opening up the phone's files and transferring by click and dragging photos that way.

Nonetheless, It is so much easier to just highlight all of the attached photos and drag them into the file which you would like to store them.


Apple fix this please. Not everyone wants to use (or pay for) your icloud storage...

Dec 10, 2020 11:00 AM in response to Ocamac

Welcome, Ocamac, to Apple Support Communities!


The reason why SawyerTX’s recommended workaround succeeds is because the images/photos always ere attachments!


If that were not the case, his workaround would not succeed!


All his workaround does is save the raw email message (which is MHTML [Mail HTML], designated as text/html, format: the latest version of that Internet standard was March 1999).


The problem is not in the format Apple Mail uses, nor in the latest implementation of the Simple Mail Transfer Protocol (SMTP) Apple may use, to transfer the email to email servers (including Microsoft Exchange servers). (Though there may be a misinterpretation on the Exchange side, if Microsoft has been their usual “feet dragging” selves, in terms of standards compliance.)


The problem y’all seem to be having is in the way Microsoft Outlook forbids you, the user, from performing bulk attachment operations (such as bulk-saves) based only upon the way Outlook chooses to display (render) your received email.


So far as anyone has been able to determine, this issue is unique to Microsoft Outlook, and its derivatives: no other email client has this misbehavior.

Dec 11, 2020 12:33 PM in response to P_D_M

Both are attachments, P_D_M.


The only difference is in appearance, with a single exception: With all email clients, except for a tiny subset (consisting solely of Microsoft Outlook, and its derivatives, so far as anyone has found), the user is able to perform bulk attachment operations (such as bulk-saves) regardless how the email client chooses to display (render) the received email.


Only that tiny subset of email clients prevent users from performing bulk attachment operations (such as bulk-saves) based solely upon how the email client chooses to display (render) the received email.


This will never be fixed, until users tell Microsoft how much this causes them trouble.


This is a matter of appearance vs. reality/actuality/functionality.

Dec 15, 2020 6:03 PM in response to Mystified-OZ

Mystified-OZ wrote:

best folks can do here is mail your complaints to favorite computer magazine and post it on Reddit 4 Chan etc

Actually, the «best folks can do here is» to give Microsoft Feedback on their email client (and its derivatives), which prevents y’all from performing bulk attachment operations (such as bulk-saves) based only upon how their email client chooses to display (render) your received email.


It wouldn’t hurt to provide Apple Feedback (using their provided Feedback mechanisms), along with the above, asking them to provide an option for users to set the default email authoring format to plain-text (text/plain).


While this last is not guaranteed to fix the issue (while the first is a guaranteed fix, if Microsoft will), at least it is something that Apple could do, without violating any Internet standards.

Dec 30, 2020 6:51 PM in response to KingCrossover

It’s amazing, KingCrossover, how many, here, are ignoring the fact that the core of the issue is not about appearances, but functionality.


Sure. In both cases (and many others) the attachments are displayed (rendered) inline with text and other features (what so many here refer to an «embedded»). (This is the Internet standard for HTML type rich-text [text/html], that’s been around since the ‘90s.)


However, in all email clients, except one (and its derivatives), you, the user, can perform all bulk attachment operations (such as bulk-saves), regardless how the email client chooses to display (render) the received email.


As I wrote:

«I challenge anyone to find another email client (that isn’t a derivative of Microsoft Outlook) with this flawed handling of your received emails.»

Jan 19, 2021 11:13 PM in response to deane160

Seems I have the same issue. I have an iphone 6S, and since the update I did in November/December 2020, (quite possibly to ios14.0) there has been a change where I email myself a photo from the phone to access it on my desktop, and the image comes through in the body of the email, not as an attachment as before the update. this takes more time and effort to copy the image into 'Paint' and rotate and resize it then save it to the desk top to then upload to a 3rd party (I do this 5 - 15 times a day in my role) this maybe a first world problem but it was so much easier/faster before the update, I could drag the file from the attachment bar at the top of the blank email, to the 'add image' on the 3rd parts webpage.


My colleague has an iphone 5 (both work phones) and this still sends as attachment (running ios13)


My IT department can't work it out and I wasted just under an hour of the New Zealand Vodafone Ninja's time going through all the settings and emailing myself over and over, and he could not work it out. hoping to get some feedback from Apple on this.


Thanks for your time.

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 12, 2021 8:54 PM in response to jaykay1320

jaykay1320 wrote:

If last week we can email photos as attachments and this week we cannot, apple has broken the phone we bought. This has to stop!! - fix it

Did you actually only update your iOS only within the last week, or so? (🤔😉)


What “broke” was that Apple’s use of the International Internet Standards, governing the composition and transfer of email, progressed, while the very tiny subset of email clients (consisting of only a single email client and its derivatives) hasn’t progressed since 2010, or even earlier.


No other email clients have any problem with the International Internet Standards, governing the composition and transfer of email.


I would not expect Apple to stay stagnant, just because some very tiny subset of email clients has been stagnant for over a decade.

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Emailing photo attachments from my iPhone 11

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