Level 1

10 points

Attachments cannot be sent with Mail Drop

I cannot send emails with larger attachments anymore.

It used to work out fine, until I updated to macOS 10.15.6 a few days ago. Whenever I try to send an email with pictures of up to 50 MB, I get a notification that attachments can't be sent by Mail Drop, and that I should try later. If I try to send anyway, I get another notification that the message cannot be stored in the 'Outbound' mailbox. The message contains one or more attachments that are supposedly too large to store there.

What's going on? I can send emails with >50 MB attachments from my iPhone, albeit with some caveats. Sending similar emails from the iCloud website works as well, but it takes long to upload the file(s).

Again, until a few days ago, I was fine. I could send emails with >50 MB emails attachments from my iCloud account or other. Now from none. I do have the 'Send large attachments with Mail Drop' checked.

iMac 21.5″, macOS 10.15

Posted on Jul 31, 2020 8:15 AM

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22 replies

JeffGS

Level 1

4 points

Sep 8, 2020 2:30 AM in response to JeffGS

Good News ! I can send the same 50K file via Mail Drop on my iPhone SE (not the new SE :) - same Apple ID as my iMac & Air. Sadly I can't find a way to compose an email with a Mail Drop attachment on my iMac or Air then pick it up on my iPhone to send the email using a functional Mail Drop ? The problem is all the email accounts, including iCloud mail server say they can't move the message on either my iMac or Air to another folder. Any ideas ? Hopefully with all these tests and info, an apple developer will know the culprit and we get a quick update, please :) Thanks, Jeff

Kikrokos Author

Level 1

10 points

Aug 3, 2020 12:05 PM in response to i_rina

Hi,

Thank you once again. Should I enable the Guest account or create a new account?

JeffGS

Level 1

4 points

Sep 8, 2020 8:25 AM in response to etresoft

Thank you from probably many others who thought it was something they are doing ! Stay safe !

Kikrokos Author

Level 1

10 points

Aug 3, 2020 9:45 AM in response to i_rina

Hi,

Thanks for coming back to me. As I said, I'm going through my usual routine: I try to send an email with around 50 MB of pictures to a particular friend. Nothing on my side has changed.

I did try to use different files and send the email to different recipients (as well as to one of my other email addresses). Unfortunately, I get the same Mail Drop notification every time, and the email won't be sent to anyone.

It's very frustrating, because nothing in my situation has changed (except macOS update to 10.15.6). And if something did on the recipient's side, the email with attached files would still be sent to the other email addresses. But it doesn't.

I've checked (again) the link to Mail Drop limits you provided, but none of the restrictions mentioned seem to apply to my situation.

When I look into my 'Sent' folder on my Mac, I can see the previously sent emails to my friend with the comprised versions of the pictures I attached. It says, for example: "Download pictures in full resolution available until August 22nd 2020".

How is it possible that it worked just fine a week ago and suddenly it doesn't? Why does it work via the iCloud website but does it take so long for the pictures to get uploaded? And why does it work on my iPhone but it take so long as well?

tygb

Level 9

65,010 points

Aug 5, 2020 8:25 PM in response to Kikrokos

As you wrote - When I receive the email in the same Mail app (on my iPhone or my Mac), the attached pictures are suddenly comprised to <10 MB.

Either the format of pictures is incorrect or you are dragging the pictures from google that are massive / they will move out from outbox when port settings are correct / SMTP server settings , check your email storage is it exceeding , creating a new test user account and configuring once again mail account is work out only .

Kikrokos Author

Level 1

10 points

Aug 6, 2020 12:09 PM in response to tygb

First things first: I tried to send the files while logged in to the Guest account, but to no avail. I got the same notification that attachments cannot be sent by Mail Drop, and that I should try again later. It's mind-boggling, because everything worked out fine just a week ago.

I'd like to stress that once more, because there's nothing wrong or "incorrect" all of a sudden with the photos I try to send. Also, they're not massive. In fact, they are screenshots made with the default Screenshot app on my Mac. However, I did try to send other pictures and photos via the Mail app on my Mac, albeit from folders on my Mac or from the Photos app. None of it works.

Now the interesting part. To add to it, I also tried to attach different files. First, I added around 100 MB of pdf files as attachments to an email followed by one with 100 MB of mp3 files. Both were sent and received perfectly and quickly!

So only with pictures (either from my Mac or the Photos app) do the trouble start! What's going on?

tygb

Level 9

65,010 points

Aug 16, 2020 10:27 AM in response to Kikrokos

But how can I get this working again in the Mail app?

You can create a web mail address with gmail and create as an Apple ID , make sure your apple id and gmail address are same and also keep the password exactly the same , sign in with system preferences using this Apple ID .

As per this article https://support.apple.com/en-in/HT202305

When you sign up for iCloud, you automatically get 5GB of free storage. You can use that storage for backups, Mail, iCloud Photos, iCloud Drive, and more. If you need more space in iCloud, you can upgrade your iCloud storage.

The size of incoming and outgoing messages (20MB, up to 5GB with Mail Drop turned on)
Check for any network monitoring software that might be using your iCloud Mail account to automatically send messages (like firewalls or internet security software that sends alerts about security issues).

Rest of the tips in the article are also followed , also incorrect settings in network , router will stop moving the mail messages out from the server its an old apple article https://support.apple.com/en-in/HT202222

The latest https://support.apple.com/en-in/HT202068

In mail preferences > general check the box of automatically try sending later if outgoing server is unavailable .

The mail attachments should be window friendly in edit section attachments you will find three options .

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Attachments cannot be sent with Mail Drop