In your example, if your inbound work server happened to have a smaller limit than your outbound home server, you would have sent the file as a normal attachment, and it would have been rejected. This would be beyond your control. Even if you knew a priori this would be the case, you would be helpless to get the Mail Drop feature to take effect in that situation.
I agree that Mail Drop has no effect in this situation, but that was also the case before Mail Drop existed. I thought I had said that previously. 😕
Yes, one could certainly use Dropbox instead, as you suggest, but I think Apple would be disappointed to learn that this easily-fixed limitation was driving people into the arms of a competitor. After all, the whole iCloud Drive system is clearly designed to allow Mac and iOS users to remain "in the family" rather than defecting to Dropbox, OneDrive, Google Drive, etc.
I don't think I necessarily agree with your statement here, Apple have offered an additional feature of its mail client and it may not be as simple to fix as it sounds. I doubt Apple are willing to or want to temporarily store, potentially ever single attachment, every single OS X 10.10 and beyond users decides to send from their computer, whether or not they are using an iCloud account.
I don't think that Apple it's attempting to stop users from using any other service if they wish to, and many, many already do just that.
By the way, Dropbox itself is now in the Mac email client business. Their subsidiary, Mailbox, has been very popular on iOS, and they're now in Beta on the Mac. They handle the attachment situation very elegantly, in my opinion. If an attachment lives within the Dropbox folder hierarchy on the sending computer, it automatically gets sent as a link. If it's elsewhere, it goes as a normal attachment. So the user can control the behavior by moving the file into or out of his local Dropbox folder before sending. Additionally, the link is hot, i.e. if the sender changes the file after sending the recipient sees the newest version each time he uses the link. This may be good or bad, depending on the situation.
Dropbox's implementation is definitely one way to attack the problem and good on them for doing so. Although, without using the app/service, it sounds to me that there is a slight difference going on too. It sounds like they are allowing a recipient limited access to your secure structure and files are where as Mail Drop is not. My understanding of it is, in Mail Drop while the files are stored in iCloud, it is not in your personal iCloud storage area. I don't know if I personally would be comfortable on relying on Dropbox, or any other service including Apple's, to allow others limited access to my data. But that could simply be my own paranoia kicking in there. 😁
It also sounds like Dropbox is not attempting in anyway to seek out what the recipients attachment limits are, just like Apple isn't and I think that is the centre of the issue. It's easy for any mail client to know what limits you have you on your server as you already have a secure connection enabled. It's a completely different story for any mail client to know what the recipients server limits are and I would suggest that if any mail client attempted to ask, the security at the recipient's end would promptly reject any such inquiry.
With regard to your other suggestion, my ISP, ICDSoft, is proud of their no-limits approach, and has no interest in implementing quotas.
Good on them, but that is also part of the problem. They also don't care if a recipient can actually receive the mail you send them.
I don't even know if this would really work for general imap implementations, i.e. whether there is a protocol for an imap sender to ask a recipient what it can handle. My guess is no, as this would require the receiving server to always be online and available synchronously to the sending server, which is a clear violation of the basic store-and-forward structure of email.
Agreed, this is in addition to my previous above.
Anyway, I will certainly take your advice to send this as a suggestion to Apple, though it grates on my nerves to do so since, in my heart, I know it's a bug not a feature!
And I think this is where we don't agree, I don't see it as a bug. I would see it as a bug, if there was a setting for a file size and it wasn't working, but as there is not actually a setting for it, it's not broken. That's why I see it as an addition feature request.
At the end of the day, Mail is simply an app for sending and receiving emails. It is one of many and each tend to excel in different features over the other. That's the good thing about choice. Apple doesn't force you or me to use Mail and as users we have the choice to use any app that it fit for our purposes, which will differ from user to user, just like any other app out there.
Thanks for the great discussion,
A