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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

Dec 15, 2020 4:11 PM in response to krwakefield

krwakefield, THIS SOLVES THE PROBLEM that is being ignored. I tried it tonight and attached a non jpeg file and it worked. Let me repeat what you said and ring some bells if I may...


But there is a workaround. As long as you also attach a non-image/picture file along with the pictures on the email, then all the files will be attached and not embedded. The additional file can be any other type (PDF, video, etc.).


I suggest using a PDF that says "Thanks Apple for messing this up!"


krwakefield wrote:

A guy at my work found a work-around since this is so critical to our business.

With Apple’s recent update to their iOS software to version 14, they have removed the ability to attach image/pictures files as attachments. Instead, they have forced the images and pictures to be embedded into the body of the email. Regardless of which app you are initiating the attachment process from, all images/pictures will be embedded.
 
But there is a workaround. As long as you also attach a non-image/picture file along with the pictures on the email, then all the files will be attached and not embedded. The additional file can be any other type (PDF, video, etc.).

I suggest using a PDF that says "Thanks Apple for messing this up!"

Good luck!


Dec 15, 2020 4:42 PM in response to Supportmenot-elppa

Oh wow, brilliant, the 1st reply out of the hundreds from my original post way back in September that actually has a work around/temp fix that does really work. Thank you, much appreciated. Now if only Apple and/or Microsoft outlook could grow up and talk amongst themselves and be proactive with a solution that will solve this ridiculously stupid fault. I won’t hold my breath though. Thanks again krwakefield, nice one. Cheers

Dec 15, 2020 5:37 PM in response to deane160

deane160 wrote:

… Now if only Apple and/or Microsoft outlook could grow up and talk amongst themselves and be proactive with a solution that will solve this ridiculously stupid fault. I won’t hold my breath though. Thanks again krwakefield, nice one. Cheers

The one and only email client (with its derivatives) that prevents users from performing bulk attachment operations (such as bulk-saves), based merely upon how said email client chooses to render (display) received emails, is entirely under Microsoft’s control.


Apple has no control over said email client.


All attempts, by any other email clients, or by those trying to devise workarounds, are doomed to be fragile: subject to being easily broken by any tiny change anywhere in the web of interactions.

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 15, 2020 6:09 PM in response to Mystified-OZ

Mystified-OZ wrote:

It’s not just Microsoft, gmail also

Does «gmail» actually prevent 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?


Last I saw the «gmail» client tested (both the App and the web interface), «gmail» didn’t have this problem.


(I sure hope they aren’t taking “marching orders”, or even “clues”, from Microsoft!)

Dec 15, 2020 6:55 PM in response to TPITTS437

For me, I went to the photos app, selected 2 pics and selected to mail through IOS mail. From within the mail, I selected just above the pic and the keyboard came up with 6 options. I selected the attachment icon. You may or may not have any pdf files in you files folder which is difficult to find. You will hopefully have a getting started pdf from adobe. I was able to send the pics original size with no problem. Now all of you photos that you send to your email clients will have a nice getting started pdf. Perhaps you could create a pdf card file with your contact info as your attachment. I looked around for the downloads (files) folder and it is not easily found. Still searching :(

Dec 17, 2020 12:19 AM in response to ultra50

I never said «outlook changed», ultra50. 😏


The problem is that Microsoft Outlook prevents you, the user, from performing bulk attachment operations (such as bulk saves), based only upon its choice of how to display (render) your received email!


This means that any attempts, by other email authoring systems, to try to make Outlook “do the right thing”™️, with your emails that include attachments, is doomed to be fragile: easily broken by any tiny change in the web of dependent systems inherent in exchanging emails.


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

Dec 17, 2020 1:00 PM in response to TPITTS437

Once again, TPITTS437, 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. (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.»

Dec 17, 2020 1:26 PM in response to Halliday

once again, skirting the issue and not answering the question in a straightforward, easy to understand manner. the fact is that prior to the Apple update, OUTLOOK, the program you apparently don't like, didn't dictate how attachments were (rendered) to use your word. however now, MAGICALLY, it's changed and now it's all MS Outlook or 365 fault.... no WAY could Apple have ANYTHING to do with that... you've done an exceptional job of towing the line, not giving straight answers and blaming other software for what originated as an APPLE issue that they have now, successfully, put onto other software MFG's. thanks! we'll take it from here.

Dec 17, 2020 1:28 PM in response to Halliday

oh and since you werent reading the other posts, you CAN FIND others with Gmail and Hotmail that have complained about this very thing. it doest matter anyway because Apple and it's employees like you who are employed to spit out this BS don't care about the end user. it's always been like that and there is no reason to believe it will change.

Dec 17, 2020 3:08 PM in response to ultra50

First, ultra50, Hotmail is the principle Outlook derivative: it, intentionally, acts similarly to Outlook—including in misbehaviors.


The direct tests of Gmail showed it to not have the misbehavior. Yes. It displays with attachments “inline” with other items and text, but it still allows users to perform bulk attachment operations (such as bulk-saves).


The one person that claimed otherwise, failed to provide further details to substantiate their claim, even when directly challenged.


Additionally, I am but a fellow user, like yourself. I have no special relationship with Apple.


I’m sorry if you are having difficulty understanding the answer to this tissue.


It took me, and others, a fair amount of time to disentangle the actual issues, from the descriptions people were writing. We read and wrote questions in multiple Discussions on this very issue. (Many are far more extensive, and older, than this one.)


However, with time, especially with the nature of the various workarounds, we (not just myself) were able to work out the root issues and causes: all lines of evidence ended up pointing to the same culprit.


Sure. There was a change in either the default email authoring format used by Apple Mail, or in the Simple Mail Transfer Protocol (SMTP) Internet standard, used in transferring email to email servers (such as Microsoft Exchange servers, as used by Hotmail), or both, in the transition from iOS 13 to iOS 14.


As it turns out, such simply triggered the preexisting issue already within Microsoft Outlook: an issue, as it turns out, many had run into in earlier iOS versions!


This is simply an example of the fragility I wrote about!


Yes. Unfortunately, not all issues have simple causes with simple solutions.


However, once one fully understands this issue, there is a single, simple solution: get Microsoft to correct the unique, errant behavior of their Outlook software, and its derivatives.


Just because Microsoft tends to “drag their feet” on Internet standards compliance, will not prevent Apple, Google, and others from moving on with standards compliance.

Dec 17, 2020 3:57 PM in response to Halliday

Halliday, you seem to be very knowledgeable on the issue that we are all struggling to cope with. I nominate you to contact Microsoft on behalf of all of us, to explain, in your more technical words, exactly what we want them to change. I, we want to be able to receive thumbnail photo attachments in outlook email.

Thanks ahead of time for your willingness to help. LOL

Dec 17, 2020 5:05 PM in response to TPITTS437

Just as with Apple, Kap2021, it is far more affective if the people experiencing the issues are the ones that provide the Feedback and “bug” reports.


As for «thumbnail photo attachments», I doubt that request will get you, or anyone, very far: that’s a rendering/displaying issue, rather than a functional-level issue.


This touches upon another aspect of the issue y’all are having:

Y’all are trying to use a tool (email) for something that is divergent from its primary use-cases: email is principally focused upon human-to-human (electronic) communications.


What y’all want is a quick and easy (and intuitive) means for transferring (often large) sets of images and photos (and, perhaps, sometimes, videos, as well).


As your desired use-cases diverge from the primary use-cases of the tool you are trying to use, y’all will increasingly run into difficulties and downright conflicts.


The tried and true old adage applies: use the best tool for the job!


Just because y’all have become accustomed to using a certain tool for your purposes, doesn’t make that tool, automatically, the best tool for the job: it’s only the one y’all are used to!

Emailing photo attachments from my iPhone 11

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