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Problem with attachment in Apple mail

I work on a Mac Studio (chip M2) with mac os x sonoma 14.4.

All my documents are synchronized in dropbox and I use the desktop version of dropbox

I have a problem for a few days now that prevents me from attaching documents to emails with Apple Mail

When I attach a document, apple mail indicates "download", but the attachment is never in the message.

Although the email starts, the person receiving it is unable to read the document because it appears corrupted and weighs 0 kb.

If I use Outlook, the problem does not exist.

If i use another computer with Apple Mail and Mac OS X Sonoma, the problem does not exist.

If I forward an email with a received attachment, the problem does not exist.

If I save a received attachement and then I send a new message with this attachement saved earlier on my Mac, the problem does not exist.

When I get an e-mail with attachments and I want to save the attachments, I choose the synchronized folder and it seems to save the files. Then when the folder opens, it is empty.

Thanks for any help

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Nancy

Thanks for posting on our forum, @Laurent N.1!

Do you mean that Apple shows a notification the file has been successfully added to your email, even though it hasn’t? Can you send me a screenshot of that notification?

Can you send me one more screenshot of an example corrupted file and how it appears on your end?

Finally, what steps are you following to attach your Dropbox files to your email?

Keep me updated.

Laurent N.1

Hi nancy, as you can see from the screenshot , next to the pdf icon the blue text "download" appears and even though the pdf weighs very little it doesn't disappear. If I send the email, it starts and it looks ok, but then the 'attachement weighs is 0 kb.

I have tried attaching documents in several ways: dragging the document to the message or clicking on the attachments icon or using the command from the menu.
The result is always the sams

screenshot 2024-03-18 alle 21.23.37.jpeg

Nancy

Thanks for that! Is this happening with other types of files besides PDFs? Like image files, for example?

Laurent N.1

It happens with any type of attachment: pdf, doc, jpg, png, etc.

Screenshot 2024-03-21 alle 07.43.01.png

As can be seen in the attached screenshot, only the type of reporting changes. In this case I have tried to attach an image.

Laurent N.1

Another interesting detail: if I want to save received attachments (via the "save attachments" command), I can only save them in a folder called "downloads" which is inside the dropbox folder. If I choose to save the documents anywhere else, even on my desktop, it doesn't save my attachments. This happens with other programs as well.
Exception: if I drag the documents to a folder, the download works (app mail and other software).

UPDATE

I installed "Spark" software (Readdle company), I have the same problems.

Walter

Hey @Laurent N.1 - sorry to jump in here, but I wanted to ask something.

Are the files you're attaching to your emails online only or available offline on your computer when you take a look at their syncing icons locally?

Laurent N.1

Hi Walter

The documents I want to send are offline.

In the meantime, I discovered something really strange: My downloads folder (which is normally located in mac os x under "user") is actually an alias of a downloads folder saved in dropbox (under folder named "Mac5" .

If I move documents (pdf, jpg, png, ...) into this folder and then attach them to an email from this folder, everything works correctly.

But only if I put them in this folder, even though they are offline documents.

Than you

Walter

Did you enabled the Dropbox Backup feature at some point in the past perhaps @Laurent N.1?

Do you see any folders being backed up in your backups online?

Laurent N.1

1) On the computer where I'm having problems with email attachement, backup is turned off.

2) Yes, I see some folders, because in the past I had activated the backup, but now I haven't used it for months.

Megan

Hi there, @Laurent N.1, would you mind clarifying the location of your Dropbox folder, as shown in your Sync tab, of your app's preferences?

If you could also clarify the exact steps you followed, when trying to attach your files, when this issue occurs; that'd be most helpful!

Laurent N.1

The dropbox location is:

Users/**/Library/CloudStorage/Dropbox

To attach documents to Apple Mail I have tried every possible way.
1) Drag and drop the document into the message with the mouse.
2) Click on the button (with icon) inside the message.
3) "File" menu, "Attach file" command.

The current situation is as follows:
1) I can send attachments contained in dropbox only from outlook. With Apple Mail or Spark (Readdle) it is impossible to.
2) I can attach documents to emails (Apple mail and Spark) only if I first move the document to the "downloads" folder.
The location of the folder is : Dropbox / Mac (5) / Donwloads
Even if I move an attachment from a dropbox synchronized folder to the desktop and then attach it to the message, it doesn't work.

Laurent N.1

Update and supplement to previous message

Update:
In addition to what was written before: I can attach a document to an email message if the attachment is in the "Documents" folder.
Address: User / Laurent / Documents

Supplement
I found another problem: When I receive a message with multiple attachments and I want to save the attachments with the "save all" command. I choose the folder where to save the documents, then clic "ok". It seems to work, but then I open the folder and it is empty.
If for the same operation, I choose the "Downloads" or "Documents" folder for destination, everything works correctly instead.
If instead I drag in attachement from the email message to the folder I want with the mouse, instead everything works correctly

Megan

Hi there, @Laurent N.1!

I'd love to know your app's current syncing status, please.

If you could also send me a screenshot of your Backup tab online shows, and another one of your app's Backup tab, that you see when accessing your app's preferences, that'd be great.

Laurent N.1

Hi Megan, here are attached screenshots of the Backup preferences

Screenshot 2024-03-25 alle 20.37.49.png

Megan

Hey @Laurent N.1, thank you for the screenshots!

What about the app's syncing status? Is it syncing content, or being up-to-date?

Laurent N.1

Hey Megan

The Synchronization is always updated.

Screenshot 2024-03-25 alle 23.04.20.png

NEW
I upgraded the operating system to MAC OS 14.4.1.
But nothing has changed.

I did a test: i deleted old dropbox backups. (backup was no longer in use anyway).
Now the "downloads" folder is gone. I can't tell if it is due to this operation or the 14.4.1 system update.

Now I tried uninstalling dropbox completely and installing from new dropbox, but unfortunately nothing changes. I can't attach documents to emails in App Mail.

Another thing I noticed, that when I start the OS, sometimes (not always) dropbox struggles to start and I have to close and reopen it. is this normal? (However, this also happens on other macs where I don't have the attachment problem).

Another question: is it normal that when reinstalling dropbox, it keeps a copy of the old dropbox (with the date of the change) in the mac os x "cloudstorage" folder (see screenshot). The old folder has all the folder hierarchy, but not the contents thankfully. Screenshot 2024-03-25 alle 23.01.52.png

Jay

Hi @Laurent N.1, I'd recommend contacting the support team directly for them to assist further on this matter.

Laurent N.1

Hi Jay, I already announced to support and they replied that the problem is known and that engineers are working on a solution. But I haven't had much support and a feeling that my problem is being taken seriously.
I wanted to write here in the community to know if other users had experienced the same problem as me.

Laurent N.1

I have not found a solution to the problem, but I have bypassed it.
I created a new profile in Mac OS X and now everything seems to work.

Graham

Hi @Laurent N.1,

I'm Graham from the Community team. I hope you're well. I just wanted to jump in here and say thanks for sharing your work around for this issue. I was wondering if you had contacted support as per Jay's instructions to try and find a more permanent fix or if you're happy to continue to bypass it using your work around. Either way, I also wanted to let you know that we have some spot prizes for Community members who share information like you have in this thread and we would like to award you one as a small token of our appreciation. Would it be OK for me to reach out to you at the email address associated with this account? Let me know and I'll get your gift on its way to you!

Thanks again, and have a great day!

Graham

Laurent N.1

Hi Graham, thank you for the information. Before contacting the community I had contacted the dropbox technical service. They had replied that the problem was known and that engineers were working on the problem, but I did not get much support.

The bypass solution I found is not a perfect solution, but it allows me to work with customers every day. I still have one problem that I cannot understand: I can only attach documents if I use Apple Mail. In some cases I have to use Spark from Readdle, but I cannot attach documents.

In all cases you can contact me at the email linked to my account.

Graham

Thank you @Laurent N.1, I'll be in touch with you shortly!