Mail drop not working all of the sudden (since 10.15.6?)

Hi there SF6,

Thank you for using Apple Support Communities!

It sounds as though you’re receiving an error message when trying to send attachments with Mail Drop in the Mail app in macOS. You’re in the right place we’d be glad to assist in seeking a solution.

Below is a resource that can help:

Mail Drop limits

This resource provides great information on Mail Drop and what limits apply when sending attachments.

If none of the listed limits apply to your attachment, we’d advise trying to send a Mail Drop attachment from another device such as a iPhone or an iPad.

If you’re able to send a attachment using Mail Drop on a iOS device, we’d advise creating a new user account to test if an attachment can be sent using Mail Drop to further isolate the issue on your Mac:

Set up users, guests, and groups on Mac

We hope this helps,

Cheers!

Hi - I just had the same problem today, 1st time using Mail Drop. Exactly as described by most other users on this thread. You should know that Apple technicians do not read the user forums, but they do read their Feedback messages.

The only way you can bring issues like this to Apple’s attention is by calling Support and discussing with an adviser, or using Feedback. Here is the link: https://www.apple.com/feedback/

Hello all

I had this problem too. This is how I have solved:

• context: I wasn't able to send with mail drop on Mail App on Mac OS Catalina. The mail account is an Apple iCloud one.
• Go in the Mail App - Preferences - Account
• choose the iCloud account
• uncheck "activate this account" or similar (I have it in italian). The account should grey out and go to the end of the accounts
• close mail
• reopen mail
• Go in the Mail App - Preferences - Account
• choose the iCloud account
• check "activate this account"

The next time I have tried to send a big attachement, it asked me again of I wanted to use mail drop, and it worked.

Hope the can help.

I had this problem starting in August 2020 after the last update. It still does not work. I do not do this often. 2-3x a month. Photo files of about 50-80MB. Not large. My limit is never reached. I send them from my GMail account. Always have, never had a problem

dp

Hey there SF6 (And DavePrev)! Hope this can help!

To confirm, you are using the Apple Mail app?

Also can you tell me what account(s) you’re using to send via Mail Drop?

I have seen lately things change for some email providers.

A good way to test is to go on the mail providers web site and send the same size attachment.

I’ve seen recently with Gmail (Google) this happen. Tried from mail.google.com, and it failed there as well saying to “upgrade to Google Drive to use mail drop”. (A message similar to that).

Although sending from an Apple ID at iCloud.com, it works just fine.

Can you confirm the email provider you’re using to send mail?

Hey digitalcan! I posted earlier when this issue was reported. Are you mail dropping from a Gmail account? Or another email provider?

I did notice when sending via mail drop at iCloud.com with an Apple ID it works just fine, same as in Apple Mail, however when sending large attachments using a Gmail account, didn’t work.

Sure enough, logging onto the email providers web site mail.google.com, you try sending the same attachment, and it prompts you to upgrade to Google Drive to be able to send large attachments. (This is a revealing test, as it points the cause to the email provider’s direction, whether it be Yahoo, Gmail, or iCloud/Apple).

I don’t know if you use a Google account or not, but other providers may start doing the same, as far as I saw, it’s not an Apple or iCloud issue, but a new requirement from the email provider, whomever they are. (Unless you’re situation is different than posted above).

Hope that helps out!

Hello, as others have reported here, I have been having this exact same problem with Mail Drop in my Apple Mail client. I also seem to have the problem in iOS using my iPhone, although it manifests slightly differently. With Apple Mail, I attach the large file and hit "send," and then get a message saying "unable to send attachments with mail drop try again later." In iOS, it initially seems like everything works fine, and I get the "swoosh" sound when I hit send on the e-mail with the large file. But then it ends up sitting in my Outbox for several minutes after which I get a message saying "one or more attachments failed to upload."

I was able to send a large file using Mail Drop by logging into my iCloud.com account using Safari. However, this is not a feasible workaround, as I never use the web-based e-mail client in my day-to-day work.

When it works, Mail Drop is a wonderful and helpful addition. I really hope that it's possible to continue using it.

Hey Carl! There are a few factors to consider. However since it works at iCloud.com, tells me the Apple server is working okay. Other factors may be the network, account settings, and even your device’s available storage.

Normally also even full iCloud storage will prevent even sending one email, but since you can send from iCloud.com, that’s probably not the case.

That said, do you use a third party/non-Apple email address for your Apple ID? Just wondering if, on your iPhone, you are actually sending from your email provider, or your Apple ID. You may also have an alias to your Apple ID, such as @iCloud/Mac/Me.com.

If you do use a third party email address for your Apple ID, can you log into their web site and try sending an attachment? That may provide the answer.

If that’s not the case, let me know, as well as the available iCloud and device storage, what accounts providers that are set up on your devices, (iCloud, Gmail, Yahoo, Etc.). As well as if the same happens on other networks/devices/email accounts/email clients/other browsers.

Also your email account storage quota may be a factor, I know I’m Apple Mail, on Mac, you can right click the Inbox or other mailbox, and select “Get Account Info”, and this will show the used and available storage for that particular account. If it is another account other than iCloud, this maybe another possible cause.

Sorry, it’s a lot of info at once, just let me/us know what you find, Hope I can help out!

Thank you for the quick reply. I have 1.88 TB free on iCloud, so the problem certainly isn't a lack of storage space in iCloud. I also have at least 40 GB of free space in my academic/work e-mail account.

My academic/work e-mail account is run through Microsoft, so if I go to the web client to send an e-mail with a large attachment, I get a message asking me to send it using Microsoft OneDrive, not Mail Drop. However, in Apple Mail on my Mac and Mail in iOS on my iPhone, I get the exact same error messages I mentioned in my previous message regardless of whether I select my work e-mail or my iCloud e-mail address to send the message. Up until recently I was able to send large attachments using Mail Drop from either account with no trouble at all.

I hope that this clarifies matters. If you have any suggestions for how to go about fixing this problem, I'd greatly appreciate it. Thanks again for your time and work on this.

Hey again! Does sending while connected to another network, even mobile hotspot make any difference?

If it’s truly an OS issue, then I’d test in safe boot and in another admin account to narrow it down. It’s usually due to one of the other factors, but not always of course. Cheers.

Hi, I have the same problem. I only exceed the mail limit occasionally, when I send a few photos, and Maildrop has worked for years, so it is a recent problem, I'm running 10.15.6. I have plenty of room in my iCloud Drive (I subscribe), and my MBP SSD Drive, and I use my Mac email account - so it is NOTHING to do with other mail providers.

It also LOSES the email - It is not in Sent or in Drafts or Outbox?? So I have to recompose the whole thing.

Not acceptable Apple!

Terry

Just seen 10.15.7 arrive so installed - it does mention about resolving an issue with iCloud File syncing. However the problem still seems to exist. It seems to me that iCloud mail syncing is still broken - I have an 80MB email in Drafts on my MBP that will not sync to iCloud (and hence to any other iCloud device). When Mail says it is "Copying Messages" it means it is copying them to iCloud. Looking at Network usage it looks like it isn't even trying to sync the email. Maybe because the email is larger than the nominal amount it tries to do something different?? Hope they get it fixed soon.

I am experiencing the same issue, regardless of whether I attempt to utilize Mail Drop on an IMAP account or upon my iCloud account. With 1.4 TB available on my iCloud account, storage shouldn't be an issue. Any updates on resolving this issue would be much appreciated.

Ditto, mail drop will not send 48.6 MB attachment through gmail account. This used to work. I called Apple and they suggested setting up a new user or reinstalling Catalina? Do they even read their own discussion community? Seems like lots are having this problem.

Hello all!

I'm also experiencing this issue since around summer. My current example is trying to send over 20BM (I shave off below 20MB and it sent out). This issue happened number of times on my MBP (mid-2013 / Catalina 10.15.7) and is happening now on my new iMac (2019 / Catalina 10.15.7).

I have followed videos on Youtube trying to untoggle Mail Drop from the Mail app via Accounts, and also untoggle the Mail feature in iCloud Drive to toggle it again and restarting the computer. Nothing works. I also have 1TB available in iCould Drive so I don't think space is an issue here.

Help!