Maildrop not working

My Maildrop has stopped working on one Mac. It had been working for years, I upgraded computers but migrated data and kept the same OS (High Sierra) as my other devices. 


The message I am getting is the standard "message too large for the server". I have checked all my settings against my other Macs which are working, and all is the same. Preference boxes are ticked to use maildrop on each of my email accounts within Mail prefs, both on gmail and iCloud addresses, and mail is active on the iCloud system pref settings. 


I have tried dumping Mail prefs in the user library, reinstalling the OS completely (twice), and yet I still can't send. The file I am trying is a 32MB photos file which I have tried sending as a single zip file as well as full size individual photo files within a single email. I am nowhere near my limit in usage or file size. I sent the same file on another Mac with the same iCloud account and email address, and it worked fine.


After doing some reading, I tried a "postfix" stop start Terminal sequence to no avail. I can't find anything in the System Library that relates to this issue in Mail, and I don't see anything in the hidden var file that would help me. Everything else on the Mac is working fine. I have read forums, tried suggestions including unticking and re-ticking the accounts prefs "use mail drop for large attachments" option box. I have even tried to reset the mail drop file limit size using Terminal.


I also never get the "Would you like to send this attachment using Maildrop" message popping up.


Any suggestions as to how to reset this function in Mail or resolve this would be greatly appreciated.

iMac 27″, macOS 10.13

Posted on Sep 18, 2020 12:27 PM

Reply

Similar questions

14 replies

Sep 19, 2020 9:58 AM in response to twonker

Are you running any VPN, Anti-Virus, or Cleaning apps?


EtreCheck is a FREE simple little diagnostic tool to display the important details of your system configuration and allow you to copy that information to the Clipboard. It is meant to be used with Apple Support Communities to help people help you with your Mac. It will not display any personal info.

https://www.etrecheck.com/


Pastebin is a good place to paste the whole report if you capture the URL while there…

https://pastebin.com/

Whew, they've changed pastebin & made it harder, but after pasting in, click Create new paste button, then Embed button, then copy the URL...

<script src="https://pastebin.com/embed_js/KuvnghqA"></script>


The important part of the above would be...


https://pastebin.com/embed_js/KuvnghqA


Workable but harder for me to work with...the Note tool on the bottom of this editor's toolbar, as shown in the image, to copy and paste the output from EtreCheck. In a Reply before you click post, look for this to add longer texts...

Sep 24, 2020 1:35 PM in response to twonker

Delete these files & restart...


  • /Library/LaunchAgents/com.radiosilenceapp.agent.plist
  • /Library/LaunchDaemons/com.bombich.ccc.scheduledtask.4D66227D-263A-4581-A61F-BF46EC65D3AE.plist
  • /Library/LaunchAgents/com.micromat.TechToolProAgent.plist
  • /Library/LaunchDaemons/com.tclementdev.timemachineeditor.scheduler.plist
  • /Library/LaunchDaemons/com.sec.faxdb.plist
  • /Library/LaunchDaemons/com.bombich.ccc.scheduledtask.7A32B37D-2333-4950-8B0C-CFF2DF9FB6FC.plist


Uninstall AVG per their directions , then run etrecheck again to see what chaff it left...


On AVG & Avast…

https://x704.net/bbs/viewtopic.php?f=17&t=8803&p=115715&hilit=avg#p115715

https://discussions.apple.com/thread/251454104?answerId=252862395022#252862395022

Sep 19, 2020 2:34 PM in response to BDAqua

Yes, I am using AVG antivirus, although I have been running that for years w/o issue when the maildrop was working fine. I also have had a vpn installed for years, but it hasn't been active for most of a year. No cleaning apps.


Maildrop worked up to 2 weeks ago or so, but I can't relate a specific event other than a security upgrade from Apple as relating vaguely to that timing. It is like the maildrop option has been turned off or is not being recognized as an option when sending. Can the maildrop option message be reset via terminal commands? Also, no other apps have been added since MD stopped being recognized by Mail


I will run etrecheck on my primary and other test admin user and advise.

Sep 26, 2020 4:49 PM in response to BDAqua

They are on my drive. I have done a zipped file, loose photos and other file types sent to another gmail address, and I have tried iCloud and gmail mail accounts and the smtp accounts that were set up with those accounts. All regular size mail is working with those accounts, just Maildrop seems to get blocked/stopped/not sent.


Thx; Rick

Sep 18, 2020 3:53 PM in response to twonker

Are you running any VPN, Anti-Virus, or Cleaning apps?


Safe Boot, (holding Shift key down at startup), does the problem occur in Safe Mode?


Safe mode attempts to repair Disks & clears lots of caches & loads safe Drivers, & prevents loading of 3rd party extensions, so if Safe Mode works try again in regular boot.


To find out if it's system wide or user specific, try this...


Open System Preferences>Users & Groups, unlock the lock, click on the little plus icon, make a new admin account, log out & into the new account.


Does it work in the new account?

Sep 24, 2020 11:32 AM in response to BDAqua

BDAqua...Did my paste to pastebin work for you? If not, it is posted below. It still seems to me that although regular size mail is working, large attachments are recognized that they are too large to send, and the system tries to launch Maildrop, but either it is not launching properly, or not connecting to the iCloud server. It then asks to try another outgoing SMTP server, which never works. After it fails to send, the reported file size shown in the mail doc then becomes just the size of the text content without attachment, as if the system recognizes that Maildrop has been triggered, but the file never gets to the MD server on iCloud.


Sep 25, 2020 3:37 PM in response to BDAqua

Hi BDAqua,


Thanks for your suggestions.


I had already uninstalled AVG, but I took the extra step of doing a find on every visible and hidden file re AVG and deleted all. I also took out every Launch agent and Daemon above, plus a few more I questioned, plus a bunch of Mail prefs, caches, and still my maildrop isn't working on any account. I also had a few remnant files from other antivirus and I removed all traces of them as well. I went through my Main library and my user library and archived (to hide their effect on the app), then dumped any other files I thought might cause an issue. I systematically tried over 50 files and folders loosely or closely related to Mail without change. My next step is to archive my entire mail file plus accounts and start completely fresh (although I also did an archive/delete of all my user accounts and set up new ones, and this did not work either. One thing I did note though, is that I created a 3rd new admin user, and this did send the attachment via iCloud, so the issue has to be in my user account somewhere.


Thanks for your thoughts and ideas. It's a bit of a head scratcher, and I am just going to keep plugging at this until it is resolved!

Cheers!

Sep 25, 2020 6:47 PM in response to twonker

Good work, yes, it something in the User's folder, Let’s see if there’s a locked file interfering.

Open Terminal & paste this command in & prefs enter, it’ll ask for an admin password & not echo what you type, wait for it to finish which will be an empty prompt unless it prints out some locked files, or Operation not permitted…

cd /;sudo find . -type f -flags +uchg

Sep 26, 2020 4:20 PM in response to BDAqua

Hi again BDAqua,


Following on from your email, this is what I am down to with the Terminal command you advised. BTW, what I did find is that Carbon Copy created a _CCCsafetynet file on my drive which I eliminated because it created duplicates of some files so the system might have been checking out the wrong location. There are two directory files that are resistant to any attempts to force delete from trash. In any case, my Mail will still not send Maildrop files, but on the bright side, my Mac is "cleaner" to this point! BTW, after deleting the CCC file, I did a safe mode start, and reinstalled the OS just in case an important file was lost with the deletions.


I hope you can add some more insight to my stubborn issue once you check the attached report.


Thx; Rick

__


This thread has been closed by the system or the community team. You may vote for any posts you find helpful, or search the Community for additional answers.

Maildrop not working

Welcome to Apple Support Community
A forum where Apple customers help each other with their products. Get started with your Apple Account.