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Mail, reply and attachment they sent if destroyed
#62431 08/28/22 11:57 PM
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kevs Offline OP
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Weird one, if no one knows, I'll call Apple.
Frequently someone send me a pdf or some or a work or some type of attachment. The attachment if good, it works, it has an icon; you can drag it to the desktop. But when I reply to the email --then it's inexplicably gone/ destroyed. All I see is a text remnant of it... ie shoes.pdf, but no real pdf can drag on desktop anymore.

Last edited by dianne; 08/29/22 04:45 PM. Reason: Moved from "Mac OS X Applications" by dianne.
Re: Mail, reply and attachment they sent if destroyed
kevs #62432 08/29/22 01:14 AM
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That is normal behavior. To save bandwidth, the attachment is not included in the reply, but the file name is included in the returned text as a reminder there was an attachment. If you want to include the attachment in the reply you will have to re-attach it to the reply from the copy you saved on your computer. To save the attachment, either drag it to your desktop or some other folder, before you reply to the message, or archive the original message. Unless the attachment has been saved, it is deleted when the original message is deleted.


"Sacred cows make the best hamburger"

- Mark Twain
Re: Mail, reply and attachment they sent if destroyed
joemikeb #62433 08/29/22 02:49 AM
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Joe thanks, usually, I'll drag the attachment to desktop. Often I Don't even reply, and usually reply after the drag.
But what do if I reply before dragging to desktop, then screwed?

Re: Mail, reply and attachment they sent if destroyed
kevs #62435 08/29/22 03:21 AM
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Originally Posted by kevs
...what do if I reply before dragging to desktop, then screwed?
As long as you've still got the original you received, the attachment will still be attached to it.

And even if you've deleted the original, it may still live - with the attachment - on your server.


The new Great Equalizer is the SEND button.

In Memory of Harv: Those who can make you believe absurdities can make you commit atrocities. ~Voltaire
Re: Mail, reply and attachment they sent if destroyed
artie505 #62440 08/29/22 05:21 PM
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kevs Offline OP
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Artie, not help, wait for Joe's reply. I reply to the email the attachment is gone. just dissolved to text. Apple Mail thing? ie

Interesting news update. I just went the email this happened last, and now its back... reappeared, the pdf girl sent me.

But that does not help me in moment, when gone.. I guess is you reply, it vanished for day or two and then may come back?

Re: Mail, reply and attachment they sent if destroyed
kevs #62444 08/29/22 09:08 PM
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Originally Posted by kevs
Artie, not help, wait for Joe's reply. I reply to the email the attachment is gone. just dissolved to text. Apple Mail thing? ie

Interesting news update. I just went the email this happened last, and now its back... reappeared, the pdf girl sent me.

But that does not help me in moment, when gone.. I guess is you reply, it vanished for day or two and then may come back?

I suspect you were looking at two different copies of the email, one in the "Sent" mailbox and the other in the "Inbox". It is very easy to confuse the two, but if you see your reply in the message you are looking at the copy in the Sent mail box.


"Sacred cows make the best hamburger"

- Mark Twain
Re: Mail, reply and attachment they sent if destroyed
joemikeb #62448 08/30/22 05:29 PM
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Joe just did test to myself sending pdf from one email to another and then did reply. Oddly the pdf was in both inbox and sent version. Go figure, but keep idea on that idea.

I do think I remember last round that triggered this post I was still in my inbox and did a reply and then saw attachment was gone.. but.. who know.. But if that even happens, it could be normal? and Why? And could reappear next day..? Maybe depends on servers or..? Trying get my head around it..

Re: Mail, reply and attachment they sent if destroyed
joemikeb #62451 08/31/22 03:26 PM
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Originally Posted by joemikeb
If you want to include the attachment in the reply you will have to re-attach it to the reply from the copy you saved on your computer.
In earlier macOS versions there's an option under Mail's Edit menu -> Attachments item to Include Original Attachments in Reply. Is that option no longer there?



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Re: Mail, reply and attachment they sent if destroyed
dkmarsh #62453 08/31/22 05:27 PM
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Originally Posted by dkmarsh
Originally Posted by joemikeb
If you want to include the attachment in the reply you will have to re-attach it to the reply from the copy you saved on your computer.
In earlier macOS versions there's an option under Mail's Edit menu -> Attachments item to Include Original Attachments in Reply. Is that option no longer there?

It is there in Catalina, but not in Monterey. In the latter the only options in the location mentioned are "Always Send Windows-Friendly Attachments" or "Always Insert Attachments at End of Message". Do those last two choices mean the attachment will, by default, be included in all replies??


On a Mac since 1984.
Currently: 24" M1 iMac, 27" iMac, M2 Macbook Air, macOS 10.15.x and MacOS 12; iPhones, iPods (yes, still) and iPads.
Re: Mail, reply and attachment they sent if destroyed
Ira L #62454 08/31/22 06:50 PM
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Ira/ DK, thanks.

I don't care if the reply has the attachment. What I notice, is that if I reply, BEFORE, dragging it to my desktop, sometimes, its gone forever, All I see then is the title of what is was with extension. What is up with that?

Re: Mail, reply and attachment they sent if destroyed
dkmarsh #62455 08/31/22 06:53 PM
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Originally Posted by dkmarsh
In earlier macOS versions there's an option under Mail's Edit menu -> Attachments item to Include Original Attachments in Reply. Is that option no longer there?

In Ventura, the option now has options.

I tested sending messages with attachments between to email accounts on the same computer, and the attachment always showed up at some level, whether or not the original email had been deleted. Then I realized this test, like the one keys' performed, is invalid because both ends are on the same machine and same copy of Mail. Mail will find the other copies even if they are on different accounts and include them in the conversation (a helpful feature). For the test to be valid, the messages would have to be exchanged between two different email accounts on two different computers.

I repeated the test using two separate computers and two separate email accounts and found...
  • If the original message containing an attachment is deleted, the attachment is deleted and irrecoverable unless extraordinary measures such as recovering from a Time Machine backup are taken.
  • Whether or not the attachment is attached to the reply depends on the settings in Mail > Edit > Include attachments with replies. The default is not to include the attachment in the reply.
  • You can open and edit an attachment in Mail, but the edits cannot be saved back into Mail. You have to save the edited version as a separate file and attach that file to the return mail.


"Sacred cows make the best hamburger"

- Mark Twain
Re: Mail, reply and attachment they sent if destroyed
joemikeb #62457 08/31/22 07:17 PM
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Thanks Joe, that makes sense you need two machines... Apple is too smart and would know.. etc.

Well then in Ventura, If I choose always include, then should solve the issue?

Trying to get my head around.. so currently, when you reply, it does not include the attachment (which is fine, why would I want to send the sender the attachment which they already have), but you are saying since does not include it, it wont even be there for me, on that original email I received from the sender to begin with..? Is just deletes poof. (if I get that correctly)... So until I have Ventura, you agree, you gotta be real diligent about downloading attachment before reply to anyone right?

Re: Mail, reply and attachment they sent if destroyed
kevs #62458 08/31/22 11:34 PM
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I just noticed this setting in Mail prefs.

If your setting isn't "Never," I wonder if setting it so would help?


The new Great Equalizer is the SEND button.

In Memory of Harv: Those who can make you believe absurdities can make you commit atrocities. ~Voltaire
Re: Mail, reply and attachment they sent if destroyed
artie505 #62459 09/01/22 12:14 AM
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kevs Offline OP
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I have that set to downloads, so it did not help in that email I received...

Re: Mail, reply and attachment they sent if destroyed
kevs #62461 09/01/22 08:58 AM
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Originally Posted by kevs
I have that set to downloads, so it did not help in that email I received...
??? There is no "downloads" setting.

To what are you referring?


The new Great Equalizer is the SEND button.

In Memory of Harv: Those who can make you believe absurdities can make you commit atrocities. ~Voltaire
Re: Mail, reply and attachment they sent if destroyed
artie505 #62463 09/01/22 03:11 PM
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kevs Offline OP
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There is download settings, but I had that checked to keep downloads, but did not prevent issue appearantly.

Re: Mail, reply and attachment they sent if destroyed
artie505 #62464 09/01/22 05:48 PM
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Originally Posted by artie505
I just noticed this setting in Mail prefs.

If your setting isn't "Never," I wonder if setting it so would help?

Good catch! I had missed that setting as well. My question is: What is the difference between a Download and an Attachment?

I have gone through a variety of test alternatives and as far as I can tell the only time an attachment is saved is when..
  1. You drag the attachment to an external folder or...
  2. You click on the paperclip icon and select where to download the file


I have yet to figure out how the Mail > Settings > General > Remove unedited attachments settings works confused


"Sacred cows make the best hamburger"

- Mark Twain
Re: Mail, reply and attachment they sent if destroyed
joemikeb #62465 09/01/22 06:28 PM
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kevs Offline OP
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Thanks Joe main issue/ question: if you don't drag that attachment to desktop, if forget, and then reply, in apple mail, it may be gone correct?

Re: Mail, reply and attachment they sent if destroyed
kevs #62467 09/01/22 07:54 PM
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PS today this

https://imgur.com/a/dvjVoih

I received an email with 8 nice photos, all displayed nice.

The second, I hit reply I saw the screenshot you see above.

And though oh, here we go... but then after send those photos retained.

BUT, sometimes don't, sometimes, gone with just that text or .pfd, or word doc etc.

Today, they stay, with new twist,: instead of one set of 8 photos, there were three sets below.. another weird issue seen.

Re: Mail, reply and attachment they sent if destroyed
kevs #62468 09/01/22 08:22 PM
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Originally Posted by kevs
Thanks Joe main issue/ question: if you don't drag that attachment to desktop, if forget, and then reply, in apple mail, it may be gone correct?

In general, that is correct, but unless you are very observant, it is easy to miss the annotation in the upper-left corner of the message, and you may be looking at a copy retrieved from the trash, the Sent mailbox, or any other mailbox and not yet erased.


"Sacred cows make the best hamburger"

- Mark Twain
Re: Mail, reply and attachment they sent if destroyed
joemikeb #62469 09/01/22 10:38 PM
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Thanks jOe, you mean the upper right? And you are saying to make sure it always says inbox, not other places?

Re: Mail, reply and attachment they sent if destroyed
kevs #62470 09/01/22 11:45 PM
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Originally Posted by kevs
Thanks jOe, you mean the upper right? And you are saying to make sure it always says inbox, not other places?

You can pick where you want to save it. Just click on "Save all..." and it will open a Finder window to select the destination.


"Sacred cows make the best hamburger"

- Mark Twain
Re: Mail, reply and attachment they sent if destroyed
kevs #62471 09/02/22 08:30 AM
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Originally Posted by kevs
PS today this

https://imgur.com/a/dvjVoih

I received an email with 8 nice photos, all displayed nice.

The second, I hit reply I saw the screenshot you see above.

And though oh, here we go... but then after send those photos retained.
That's expected.

The second you hit "Reply" your screen changed from the email in your in box to the response email, which by default doesn't include the original images...only the references to them seen in your screenshot.


The new Great Equalizer is the SEND button.

In Memory of Harv: Those who can make you believe absurdities can make you commit atrocities. ~Voltaire
Re: Mail, reply and attachment they sent if destroyed
joemikeb #62472 09/02/22 09:30 AM
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Originally Posted by joemikeb
I have yet to figure out how the Mail > Settings > General > Remove unedited attachments downloads settings works confused (Emphasis added)
I guess some copywriter's left eye wasn't pointed in the same direction as hir right eye. tongue

I found this...
Delete email attachments
In the Mail app on your Mac, select a message that includes one or more attachments.
Choose Message > Remove Attachments.
The message remains in the mailbox and is annotated to indicate that all attachments were manually removed. For IMAP accounts, attachments are also deleted from the mail server and can’t be retrieved.
When you delete a message that includes an attachment, the attachment is deleted too. To change this setting, choose Mail > Preferences, click General, click the “Remove unedited downloads” pop-up menu, then choose an option. Mail doesn’t delete attachments that you have saved.
I've got no idea what "unedited" means in this context, though.

And in a different vein, I found this, which kevs may find helpful.


The new Great Equalizer is the SEND button.

In Memory of Harv: Those who can make you believe absurdities can make you commit atrocities. ~Voltaire

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