iOS 7: Unreliable sharing by email

Posted by Pierre Igot in: iPad
December 21st, 2013 • 4:42 pm

I recently bought an iPad Air to replace my old, first-generation iPad, and this means that I have finally been able to upgrade to iOS 7.

iOS 7 is a very mixed bag as far as I am concerned (I have to agree with Jared Sinclair, for example), but if there is one thing that has been irking me to no end since upgrading, it is Safari’s “Share” button, and more specifically its option to share a site’s URL by email.

From a purely esthetic point of view, I find the Share button in iOS 7 atrociously ugly:


But what really pisses me off is that:

  1. When I select the “Mail” option, enter the email address of the recipient, and tap on “Send”, sometimes there is no “swoosh” sound or anything that confirms that the email has been sent. Which is particularly problematic because…
  2. I cannot get it to work reliably.

Safari is configured to send these emails from my iCloud account, using iCloud’s own SMTP servers. So it should work anywhere in the world. I have also configured iOS to always send me a copy of anything that is sent out from the iPad via the Bcc: field. (This is the only way to get sent messages for POP accounts on my main computer, which is important for my non-IMAP accounts. This setting cannot be adjusted on a per-account basis.)

The iPad is a family device, which means that both my wife and I use it. We both use the “Share” button in Safari, mostly to send URLs to ourselves. Sometimes it works, sometimes it doesn’t.

When it works, and when my wife sends herself the URL to a site, I normally get a copy because of the Bcc: thing. When I send something to myself (even to one of my email accounts other than the iCloud account), I do not get a copy also sent to my iCloud account, even though it’s right there in the Bcc: field. But (when it works) I do get the email at the destination account, and I also get the sent message in the “Sent” mailbox for my iCloud account, which is configured as an iCloud — i.e. IMAP — account in Mail on my Mac.

When it does not work, on the other hand, no one gets anything. My wife does not get her copy, I don’t get the copy supposedly sent via Bcc:, and I also don’t get the sent message in the “Sent” mailbox for my iCloud account.

Why? I have no idea. I have tried various things, with mixed results. I have noticed two possible issues, but I don’t know if they have anything to do with anything.

One is that there might be a problem with sending mail from Safari when the Mail app itself is somehow stuck because it cannot connect to one of the several servers used for my various email accounts (even if it has nothing to do with iCloud). Like the Mail app in OS X, iOS’s Mail has a bad tendency to display modal dialog boxes saying that the password is incorrect, or that the server is not responding, or whatever. Since I don’t regularly use Mail on the iPad, I don’t necessarily notice these problems. So maybe Safari’s Share function fails when Mail itself is stuck in the background because of one of those modal dialog boxes. Like its OS X counterpart, iOS’s Mail seems to be unable to “degrade gracefully” and handle less than optimal situations. Apple has a history of failing to handle flaky Internet connections and intermittent network problems gracefully in its software. In Apple’s world, it seems, network health is always perfect and there is no need to test the software in situations where network reliability might be compromised.

The other thing that I have noticed is that, in the configuration for my iCloud mail account on the iPad, at some point the “Allow Sending From” section (under “Advanced”) included several aliases, but not the original address, even though it is actually my Apple ID (which cannot be updated, of course)!

However, when I look at it now, I see that the original address is back in the list and is even greyed out, presumably precisely because it is my Apple ID and cannot be changed (meaning that I cannot disallow sending from that alias, which makes sense):


How did it right itself? I don’t know. It might be because earlier this afternoon I visited my Apple ID page on Apple’s servers and tried to check to make sure everything was in order. Maybe that somehow shook iOS’s own configuration out of its torpor.

Finally, I also cannot help but wonder whether Apple’s sometimes overzealous spam filters don’t have a tendency to treat emails that only contain a URL (with no accompanying text) as spam. I hope not, and I have just been able to send myself a couple of URLs this way successfully, so if spam filters are involved in this problem, it is definitely intermittent.

I have also just noticed that there is similar flakiness in the “Share” feature in the Photos app. I just tried to send myself the screen captures above. It didn’t work at all the first time, even though I got the “swoosh” sound confirming the sending out of the emails. Then I tried again, this time editing the email before sending it by using my alias instead of my alias, and by adding some text in the body of the message before the picture, and then it worked just fine. What the hell is going on here?

Basically, at the end of the day, I don’t really know much more than I did when I started researching this particular issue. It’s rather frustrating. And it’s particularly problematic to have no way to make sure that URLs sent by email via Safari’s “Share” feature or pictures sent by email via Photos’s own “Share” feature on the iPad actually get delivered to their recipients.

I cannot say that I am too impressed.

Comments are closed.