Email photo as attachment, not embedded, in iOS 14

SOLVED!

i figured out the issue with embedded vs attachment on IOS 14. If you send an email in HTML, it will always embed the photos. If you send Plain Text, the photo will be attached. Any formatting in the email triggers HTML. It could be your signature or any other text if it is bold, colored, underlined, italic etc.

If you have a formatted signature, you cant just change it, you have to delete it by selecting ALL then backspace to delete it. Then type your signature as plain text and your pictures will be attachments

My ipad came defaulted with a formatted signature, after changing it, this worked

My assistant found a work around. Record a 1 second video. Go into your photos and select all your photos and the video send as you used to prior to IOS 14 and they will all go to the email as an attachment. Make it a really short video or it makes the file rather large.

WORKAROUND:

I have found that the native built-in email app and the Gmail app both embed the photo after upgrading to iOS 14. However, I found that the Outlook app still sends it as an attachment. The Outlook app client can be used with Microsoft accounts (Outlook.com, Hotmail.com, 365, etc), Gmail, iCloud, etc).

I really don't understand the people here who are insisting its not an Apple problem. Apple made a change to their emailing of Photos and now it doesn't work effectively for a **** of a lot of people. Blaming Microsoft is pretty stupid as Office 365 is rapidly becoming the largest corporate email user base in the world. Apple have made a change and they could just as easily fix it. They have done it before years ago - It was exactly the same result to users - We stopped being able to attach photos and instead they were embedded. Its pretty petty to just say blame Microsoft and stick your tongue out.

Certainly I've tested and with Gmail I can extract the attachment fine and if I send it with Microsoft Outlook on my iphone it them shows as an attachment when its received.

There is obviously something about the encoding they are using though as Outlook does have a "Save All Attachments" option under file but it doesn't think there are any. Surely between the two of them you'd think they could work it out.

Thank you, Scamp468.

Scamp468 wrote:

Since there have been many posts on this subject, I felt should summarise what works for me. I am on iOS 14.4.

I don't like the idea of using the text app as I believe this just converts the message to an MMS, compresses the files and (in my case anyway) incurs extra charges.

Yes. «[U]sing the text app» does send the message as «an MMS», which gets converted to an email along the way to the email server destination. (Probably as soon as it leaves the phone network.)

The extra compression of the files is probably a simple byproduct of using MMS: it’s not intended for high resolution use.

The email that it gets converted to probably has no textual formatting, or even formatting of the attachments. It is probably a plain-text (text/plain) email. (Who knows what attachment method [Content-Type: multipart/related; or Content-Type: multipart/mixed] may be used for the attached images.)

This may suggest that a plain-text (text/plain) email might “kick” Outlook into “doing the right thing”™️ with the attached images.

Unfortunately, there is no guarantee.

In fact, even this workaround is fragile—subject to being easily broken by any tiny changes in the web of interactions involved in transferring MMS messages and emails—that could stop working at any time.

1.Attach a very short video with your photographs. This makes the photos present as attachments. The receiver just discards the video. Not everyone likes this way around so:

From N-K-O’s investigation, we know that this works by forcing the Content-Type to multipart/mixed, rather than the multipart/related Content-Type that is appropriate when all attachments are of the same filetype.

For whatever reason, Outlook doesn’t allow users to perform bulk attachment operations (such as bulk-saves) if the Content-Type is multipart/related. (If anything, the opposite would make more sense, if this had anything to do with “sense”. Instead, it probably, simply relates to a “kludge” in Outlooks email composition algorithms: why analyze whether all attachments are of the same filetype; just always use Content-Type multipart/mixed, regardless! Hence, if Outlook runs into Content-Type multipart/related it “knows” that it is dealing with non-Outlook content! [There are likely many more such “gotchas” in Outlook’s algorithms.])

Hence, the added attachment need not be a video, but any filetype that is different from the primary attachments.

2. Use a g-mail (or I presume any other non-MS/Outlook derived e-mail system) as your default sending account on your iPhone. The photos then display at the other end as attachments, seemingly even when receiving through MS Exchange. If they are not presented this way with an MS derived e-mail account, send to the g-mail account. This always works for me.

This workaround is why we know that there is a portion of the issue that involves Exchange servers.

Unfortunately, we know much less about the details of this portion of the issue.

However, it should be obvious to anyone that if it were not for the way Outlook prevents its users from performing bulk attachment operations (such as bulk-saves), based upon email characteristics known only to its programmers, this would all be a non-issue!

In other words, if Outlook (and its derivatives) were fixed, so it allowed users to perform bulk attachment operations of their received email with attachments, we need not bother with any vagaries with Exchange servers.

I am very definitely non-techy so I hope this helps some of us out there.

You have provided good help. Thank you.

I don't think method number 2 works… I used my Yahoo email account to send a test email to the same account, therefore bypassing Outlook completely, and the pictures are embedded UNLESS I do the 1 second video trick.

Scamp468 wrote:

1. Hi, This has come about since Apple upgraded to iOS14. It is now up to 14.4. It seemingly affects all Microsoft authored e-mail clients like Hotmail and Outlook. There are a few workarounds, but the two which I have used are:-

Attach a very short video with your photographs. This makes the photos present as attachments. The receiver just discards the video. Not everyone likes this way around so:-

2. Use a g-mail account (or I presume any other non-MS/Outlook derived e-mail system) as your default sending account on your iPhone. The photos then display at the other end as attachments, seemingly even when receiving through MS Exchange. If they are not presented this way with an MS derived e-mail account, send to the g-mail account. This always works for me.

I hope this helps.

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.

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...

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.

Lotus9999 wrote: I don't think method number 2 works… I used my Yahoo email account to send a test email to the same account, therefore bypassing Outlook completely, and the pictures are embedded UNLESS I do the 1 second video trick.

Scamp468 wrote:

1. Hi, This has come about since Apple upgraded to iOS14. It is now up to 14.4. It seemingly affects all Microsoft authored e-mail clients like Hotmail and Outlook. There are a few workarounds, but the two which I have used are:-

Attach a very short video with your photographs. This makes the photos present as attachments. The receiver just discards the video. Not everyone likes this way around so:-

2. Use a g-mail account (or I presume any other non-MS/Outlook derived e-mail system) as your default sending account on your iPhone. The photos then display at the other end as attachments, seemingly even when receiving through MS Exchange. If they are not presented this way with an MS derived e-mail account, send to the g-mail account. This always works for me.

I hope this helps.

By the way, for method number 2, to be clear, you are saying users can still send pictures with the default Mail app on the phone, and as long as they simply choose the FROM address as being their Gmail account, it should work.

As I indicated above, it does not work, which does not surprise me either. The problem is with the default iOS Mail app. Not the account that the emails are sent from. Which is exactly why despite me sending the email from my Yahoo or Gmail accounts, they continue to show up as embedded pictures.

The solution seems to be instead to use a different email app. At least using Outlook seems to work - and ONLY if you initiate sending the photos from the Photos app. If you start within Outlook and attach pictures, you end up with embedded pictures.

Remains to be seen whether the same holds true if using other third-party email apps.

Lotus9999 wrote:

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.

- 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 …

Lotus9999 wrote:

Lotus9999 wrote: I don't think method number 2 works… I used my Yahoo email account to send a test email to the same account, therefore bypassing Outlook completely, and the pictures are embedded UNLESS I do the 1 second video trick.

Scamp468 wrote:

1. Hi, This has come about since Apple upgraded to iOS14. It is now up to 14.4. It seemingly affects all Microsoft authored e-mail clients like Hotmail and Outlook. There are a few workarounds, but the two which I have used are:-

Attach a very short video with your photographs. This makes the photos present as attachments. The receiver just discards the video. Not everyone likes this way around so:-

2. Use a g-mail account (or I presume any other non-MS/Outlook derived e-mail system) as your default sending account on your iPhone. The photos then display at the other end as attachments, seemingly even when receiving through MS Exchange. If they are not presented this way with an MS derived e-mail account, send to the g-mail account. This always works for me.

I hope this helps.

By the way, for method number 2, to be clear, you are saying users can still send pictures with the default Mail app on the phone, and as long as they simply choose the FROM address as being their Gmail account, it should work. …

Actually, not, Lotus9999.

What must be the case is that the outgoing (SMTP) email server must be a Gmail server, or, really, anything other than a Microsoft Exchange server.

So. One can «simply choose the FROM address as being their Gmail account», and not have it work.

… As I indicated above, it does not work, which does not surprise me either. The problem is with the default iOS Mail app. Not the account that the emails are sent from. Which is exactly why despite me sending the email from my Yahoo or Gmail accounts, they continue to show up as embedded pictures. …

Furthermore, of course, once again, the issue is not in the appearance, but in the functionality: does Outlook (or another email client) allow you to perform bulk attachment operations (such as bulk-saves), regardless of appearance?

…

Remains to be seen whether the same holds true if using other third-party email apps.

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?

Halliday, you mention "International Internet Standards" that govern email creation ad nauseam. So who is this mysterious email committee? The closest I can find is the Internet Engineering Task Force (IETF) https://www.ietf.org/about/who/ I sent them an email with a link to this thread 11 days ago and asked them to chime in. I haven't heard back. Maybe you have contacts from when you were in the business world who you could leverage a favor to resolve this for 118.1 million iPhone users in the US. We'd surely give a word of thanks.

The issue clearly started the day we upgraded our iPhones from iOS v13 to v14. You mention that it started in September. It's a weird coincidence that iOS 14 was released September 16, 2020. I first posted my work-around to use the Outlook app on Jan 1. I did this merely to help the millions of iOS users because this thread had proved to me that they needed a work-around. I will prove that the issue is not with Outlook, nor Exchange, nor MS 365. The proof is not by *sending* an email and seeing if it arrives as an attachment. The proof is prior to clicking "Send". Here are the steps I followed: Open Photos and select the desired photo, click the upload button, select the native iOS email app; notice that the picture is embedded in the body of the email. If the email starts with an embedded photo in draft format on the iPhone, it's not going to magically convert to an attachment when it hits an Exchange server. However, when I select the Outlook app as the option to upload the photo, then the drafted email shows the picture as an attachment. Therefore, the issue has nothing to do with Outlook, nor Exchange, nor MS 365. The issue is obviously caused by the iOS upgrade from v13 to v14.

As for solutions to offer to the followers of this thread, I personally use the Outlook app with both a 365 account and my Gmail account. It will work with any email server. iOS used to not allow changing the default mail app away from the native app, but that is no longer the case. I confirmed that I can set my default email app to Outlook or Gmail. If you are trying to get photos from your phone to your own computer, using OneDrive, Google Drive, iCloud Drive, or Photos (the photo roll from your iPhone that is backed up to iCloud).

I have been in tech support for 22 years. Sometimes work-arounds are the best we can offer. I don't work for Apple, Microsoft, or Google so I have very little influence over their direction of services and options. I have used Microsoft forums to gain attention to desired new features to add or return old features that were removed. I don't recall if it ever worked.

TarHeelTech wrote:

…

The issue clearly started the day we upgraded our iPhones from iOS v13 to v14. You mention that it started in September. It's a weird coincidence that iOS 14 was released September 16, 2020. …

Only this latest incidence started with iOS 14. There have been many other instances, through the years, that occurred with a number of previous iOS versions.

The longstanding answer is:

«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.)»

This will continue to be the case, so long as the responsible company does not correct the issue with their products.

… I first posted my work-around to use the Outlook app on Jan 1. I did this merely to help the millions of iOS users because this thread had proved to me that they needed a work-around.…

You continue with:

I will prove that the issue is not with Outlook, nor Exchange, nor MS 365. The proof is not by *sending* an email and seeing if it arrives as an attachment. The proof is prior to clicking "Send". Here are the steps I followed: Open Photos and select the desired photo, click the upload button, select the native iOS email app; notice that the picture is [has the appearance of being] embedded in the body of the email. If the email starts with [what appears as] an embedded photo in draft format on the iPhone, it's not going to magically convert to [something that y’all call] an attachment when it hits an Exchange server. However, when I select the Outlook app as the option to upload the photo, then the drafted email shows the picture as -something y’all call] an attachment. …

You then conclude:

… Therefore, the issue has nothing to do with Outlook, nor Exchange, nor MS 365. The issue is obviously caused by the iOS upgrade from v13 to v14. …

Unfortunately, as you can see in my additions to your comment, you, like so many others, are judging based only upon superficialities (appearances) and circumstantial evidence.

If, however, you could actually demonstrate that the emails authored by Apple Mail are not actually emails with attachments, but do something else, that is not consistent with the International Internet Standards that govern email creation and interchange; then you would have something to accuse Apple of.

On the other hand, the counter evidence we have, before even checking the Raw text of the emails created by Apple Mail, are as follows:

1. No email clients, except Outlook, and its derivatives, have any problem allowing their users to perform bulk attachment operations (such as bulk-saves) on received emails from Apple Mail, regardless of appearance.
2. Even Outlook recognizes the attachment structure of received emails from Apple Mail: Within Outlook, simply save the email as HTML. You’ll find that all the attachments have been saved as files within the directory/folder Outlook creates.

Now. As I recall, from when I used to use Outlook in the governmental/corporate world, Outlook was able to allow me to view the Raw textual form of received emails.

Using that, one could see, once and for all, whether the structure of emails, from Apple Mail, adhere to the International Internet Standards that govern email creation and interchange.

… As for solutions to offer to the followers of this thread, I personally use the Outlook app with both a 365 account and my Gmail account. It will work with any email server. iOS used to not allow changing the default mail app away from the native app, but that is no longer the case. I confirmed that I can set my default email app to Outlook or Gmail. If you are trying to get photos from your phone to your own computer, using OneDrive, Google Drive, iCloud Drive, or Photos (the photo roll from your iPhone that is backed up to iCloud). …

That Outlook will work well in communicating emails from itself to itself should be completely unsurprising, to anyone, even if Outlook were to completely violate the International Internet Standards governing email creation and interchange.

The important part is to get it to work well with all standards compliant email clients.

(Continued …)

Halliday, sorry if you felt interrogated or deposed. You said you expect better of me. I’ll give you my best. Since you are a scientist, please try this experiment. Let’s remove Microsoft as a variable; no Outlook, no 365/Exchange.

On an iPhone running iOS 14, open Photos. Select a photo and click the upload icon. Select the native built-in app, Mail. Using either an iCloud.com or gmail.com account (don’t use Hotmail or any other Microsoft account) send the picture to your iCloud or Gmail address. How did it arrive? For me, it came embedded. Now the real moment of truth. Open Sent Items. Open the email you just sent. Is the picture embedded? If so, then I ask you - “What’s Microsoft got to do with that?”

PS - you claim to have mentioned the IETF previously. I went through all 45 pages and didn’t see you mention them specifically; only mentioning the generic “internet protocol standards”. I had to investigate who creates those standards. To your credit, it appears to be legit. It would have been helpful if you included a link to their mission earlier to lend credence to your explanation. However, I have yet to get a reply to my request for them to read this thread and provide their expert opinion. I also asked them to leverage their influence to get resolution; I don’t care if the issue with with Apple (it is) or Microsoft. Surely they write the protocols and standards so they must have some clout in the industry.

Friend of the internet who came here desperate for a solution to send an picture as an attachment to an email, there’s good and bad news. The bad news is that there is not a setting in the built-in Mail app. The good news is that there is a work-around - simply install the Outlook app; it will work with non-Microsoft accounts, such as Gmail or your favorite ISP. Maybe one day Apple will fix it (or Microsoft if you’re buying what my scientist friend is selling). If it’s never fixed, then get used to the Outlook app. You can actually have both the Outlook app and built-in Mail app configured for the same account. You only have to use the Outlook account whenever you want to send a picture as an attachment.

Congrats to those of you who scrolled through 45 pages of commentary without a suggestion for a work-around. My apologies for the amount of time you wasted. Peace ☮️ ✌🏻

Apple made a change in IOS 14 to stop people from being able to send pics as attachments when you use Apple's mail. Period. An Apple senior manager confirmed this to me.

It has nothing to do with Microsoft, so don't muddy the waters. In fact, if you open a browser and sign into your hotmail account there, the pics will send as attachments. But if you use the Apple mail system to access your hotmail account, the pics will be sent embedded. THIS is what people are angry and frustrated about. And THIS is why people need to bombard Apple with complaints, demanding it reverse this terrible decision.

Apple decided to make this change in IOS 14 that stops people from being able to send photos as attachments. I have no clue why the company made this change. But this is why we're hoping everyone will bombard Apple with complaints, asking it to reverse this change.

In the meantime, I've found two workarounds:

1. First way - If you send a small video file with your photos, all will show up as attachments. Yay!
2. Second way - If you use a browser to access your hotmail/outlook account (instead of the mail app), it will send all photos as attachments the way it used to be.