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

Jan 9, 2021 5:12 PM in response to PLCornell

Welcome, PLCornell, to Apple Support Communities!


Apple is not here, nor do they monitor this forum to see what issues users are having.


We are but your fellow users, trying to help other users, like yourself.


If you wish to get a message to Apple, about their products, you will be best served by sending Apple Feedback through their provided mechanisms, such as Product Feedback - Apple.


However, it’s amazing 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.»


As for whether your photos are in JPEG format, or a more modern, more efficient format, you can change the settings on how photos you take with your phone are stored on your phone: Settings -> Camera -> Formats: High Efficiency vs. Most Compatible (JPEG).


(Unfortunately, this will not solve the issues of the «one (and its derivatives)» email client, that prevents its users from performing bulk attachment operations [such as bulk-saves] based only upon how said email client chooses to display (render) your received email.)

Mar 4, 2021 10:17 PM in response to BJP73

Welcome, BJP73, to Apple Support Communities!


It may help to read my comment to Scamp468, at https://discussions.apple.com/thread/251807601?answerId=254744057022#254744057022.


(There are other reasonably good comments within this Discussion, as well as that one I referenced, above, and at least one other Discussion, also more extensive than this one.)


Unfortunately, the «multi step process», to which you refer, is only “necessary” on a very tiny subset of email clients, all created by the same company.


Furthermore, since the responsible company is not Apple, there is no fix that is within Apple’s power or authority.


All anyone (other than that responsible company) can accomplish are fragile workarounds, that easily break with any tiny change in the web of interactions involved in transferring emails.


Such a fragile workaround broke with iOS 14, as it had in various previous iOS versions over many years.

Mar 8, 2021 7:55 PM in response to ultra50

Welcome, ultra50, to Apple Support Communities!


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 of 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 trifold:

  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. (Your feedback matters to Microsoft)
  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.)


I realize this answer is not what many want to hear (much like some other answers people receive, here, on Apple Support Communities).


Now. All that being said, there are some workarounds that have been shared, here, and in related Discussions.


Unfortunately, all such are but fragile workarounds, as per item 3, above.


Additionally, y’all should always feel free to provide your Feedback to Apple through their provided Feedback Mechanisms: Product Feedback - Apple.


(Be aware that Feedback that tries to claim that the problem is with Apple Mail “embedding” photos/images/pictures/etc., rather that “attaching” them, will likely result in something like the following “response” [which will never get back to you, unfortunately] from the responsible Apple Software Programming supervisor: “Apple Mail already sends, and always has sent all files as attachments. NEXT!”


That’s why I have been trying to educate people on the realities, so y’all can make better informed decisions, along with where, with whom, and what sort of feedback may be best to lodge.


However. As always, what you believe and what you do is up to you.)

Nov 4, 2020 7:54 PM in response to deane160

Microsoft Outlook is your answer to you issues and frankly Outlook has always worked better than the Apple Mail app and continually improving. I too experienced the same issue and in the past iOS versions, Exchange email accounts would still attach photos, but not with IMAP and POP type accounts. Since iOS14 release all email accounts will not attach the photos but rather inserts photos into the email body.


Techie IT Australia

Nov 11, 2020 11:42 AM in response to deane160

Hi, I’m now using outlook, if i could delete Apple mail I would. Outlook allows you to send jpgs as attachments as long as you start from the jpg, if you start from a new email it will embed them.


Knowing Apples modus operandi there will be some paying service (probably involving the cloud) coming up which will miraculously mean you can attach jpgs and screenshots as before.


You may also have noticed if you forward emails from mail which had attachments, they will not forward the attachments, in some cases it is not possible to forward the email at all.


I’m accelerating my move to Microsoft and android as this behaviour is disgusting. Apple hardware is for the toy market, they are not capable of being reliable business tools. I hope many more will follow suit.

Nov 26, 2020 1:20 AM in response to iW00

There is a bug in the HTML portion of the email created on an iphone in IOS14. This is something that iphone users cannot control and must be fixed in the iphone mail tool. It may have also been a bug in earlier versions of IOS. The problem is this: The image is embedded in the HTML portion, but there is a keyword missing in that part of the email. The missing keyword is: <!DOCTYPE html>

If you look at the "raw source" on the Apple mail tool on Macs (Mail->View->Message->Raw Source) when viewing the email, you can see the error. See below for an example of the beginning of that part of the email. The image is embedded there, but if <!DOCTYPE html> is missing, then the mailtool will not display that version of the email. Instead, it displays the first part of the email with plain text and no images at all.

I already filed a bug report a few minutes ago.


There is a workaround once a user receives the email on their Mac. They can select the email in mailtool, then select File->Save As and choose Format "Raw Message Source". This creates a file with .eml at the end of the name on your desktop or wherever you select. Then you can edit that .eml file with TextEdit (don't just double-click to open it...instead, right-click/two-finger select the file and choose Open With->Other and scroll down the list of applications until you find TextEdit.app, then choose that). In TextEdit, insert <!DOCTYPE html> in the correct place and save the file. Then go back to mail tool and choose File->Import Mailboxes, choose Import data from Apple Mail, then Continue, then select the file you changed. This creates a new mailbox with a name like Import or Import-2. Select the mail item with in it and you can see it with the change, and the image should then show up. You can then move the email into your inbox or forward it or whatever you want to do with it.


I should point out that there is another problem. This worked find when the embedded image was "jpeg" on Mac OS X Mojave, but when I did the very same thing with an IOS email that embedded a "heic" image (Apple's own image format I think?), the image still does not display when viewing in the mac OS X mailtool. It seems heic might not be supported on Mojave? But you will see that other images and fancy html will work whereas it wouldn't have before.


Sample of *corrected* syntax of the content of the email, with <!DOCTYPE html> inserted after the Content-Type statement and before the <html> tag:


--Apple-Mail-F085916F-874E-4FE6-82C8-2EAB3371F4A4

Content-Type: text/html;

charset=utf-8

Content-Transfer-Encoding: quoted-printable


<!DOCTYPE html>


<html><head><meta http-equiv=3D"content-type" content=3D"text/html; charset=3D=

utf-8"></head><body dir=3D"auto"><div dir=3D"ltr">

<div><br></div>

<div>Fry 1 pound diced chicken in peanut oil.</div>

(etc.)

Nov 27, 2020 5:04 AM in response to jamesfrompleasanton

Dear Apple folks,


I have been fighting this issue since the update and finally just found a very easy workaround to save image for microsoft email and windows computers. Simply double click on the embedded picture, nothing will happen, then right click on image and you will be given the option to Save as picture. You can then at very least save the picture to your computer as a jpeg. This does not resolve the issue of the picture being embedded in the email, but at least makes the picture a little easier to save for reuse.


Frank

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.

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!

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Emailing photo attachments from my iPhone 11

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