Category Archives: email

Email hassles with Android and Exchange: couldn’t open connection to server

I have an Asus/Google Nexus 7 which is set up to receive mail from Exchange 2010.

At least, it was. Some time ago it stopped receiving mail. When the mail client tried to sync, I got this message:


“Couldn’t open connection to server due to security error”.

The message is not particularly clear. I went back into the account settings and verified everything (including Accept all SSL certificates, since mine is self-signed) and it was all fine – as I knew it would be, since it used to work.

The error, it turns out, is to do with ActiveSync policies. Exchange is detecting that the device is not in conformance, and refusing to sync. Odd, since my ActiveSync policies are relaxed and allow anything.

I removed the account and added it back. Ah, now I have this dialog:


I tapped Activate and everything was fine. Mail now syncs again.

I am still not sure how you find this dialog if it does not pop up automatically.

Why Outlook rules copy a message when you asked for it to be moved

Ever wished computers had a “do what I mean” button?

Here’s a case in point. I use Outlook/Exchange rules to sort email into subfolders. I set up a new rule, and was annoyed to find that while messages were correctly being moved into the selected folder, they were not being deleted from the source folder. In other words, I’d asked for move but I was getting copy.

Bug in Outlook/Exchange rules? I don’t entirely trust them; but on this occasion it was my fault. The problem: these messages also matched another rule, which moved them to a different subfolder – the one, in fact, that I was treating as the “source folder”. When confronted with two rules that both move a message, Exchange makes a copy. Whether that is the right behaviour is arguable, but it is not a bug.

Here’s the solution. In the Actions for the rule, also check the option to “Stop processing more rules”.

Problem solved.

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Apple Snow Leopard and Exchange: the real story

Apple’s Snow Leopard (OS 10.6) came out last week, and one of its most hyped features is native support for Microsoft Exchange. Here’s what Apple says:

With Snow Leopard, the Mac is the only computer with built-in support for the latest version of Microsoft Exchange Server. So you can use your Mac — with all the features and applications you love — at home and at work and have all your messages, meetings, and contacts in one place.

What this means is that eager Mac users will be upgrading to Snow Leopard and expecting to be able to connect to Exchange at work with Apple-style “it just works” ease of configuration.

The truth is more complex; and I’m disappointed with both Apple’s publicity and the number of reviews that have simply reported its claims without investigation. That said, it is a tricky subject, and I have some sympathy with Apple, which is doing more or less the right thing at a technical level.

Configuring Snow Leopard Mail to use Exchange

The first thing to understand is that there are myriad ways of connecting to Exchange, including:

  • MAPI, which is Microsoft’s proprietary API
  • IMAP, which is a standard protocol for server-based email
  • ActiveSync, which is a Microsoft protocol used for mobile devices
  • RPC over HTTPS, effectively MAPI over SSL, enabling Outlook to connect from outside the network without VPN
  • Outlook Web Access, a web UI for Outlook
  • WebDAV, now deprecated
  • Exchange Web Services, which communicate using SOAP XML messages

Which of these protocols are actually enabled, and whether they are published beyond the internal network, is a matter for Exchange admins to configure.

The usual generic method to connect to Exchange from a miscellaneous client is IMAP, and this is exactly what Apple supported in Mail before Snow Leopard, and still supports. IMAP works pretty well in my experience, but it is only for email and does not expose any Exchange-specific features.

Snow Leopard adds support for Exchange Web Services (EWS), giving a much richer level of access to Exchange. First snag: EWS is only supported in Exchange 2007, which is why Apple says in its small print:

requires Microsoft Exchange Server 2007 Service Pack 1 Update Rollup 4

Second snag: even EWS does not all the features of MAPI, and some features (notably public folder support) were only added in Exchange 2007 SP2, which has just been released. This probably explains why Mail does not (as far as I can tell) support public folders.

The key thing to understand is that Snow Leopard is not using the same protocol as Outlook and therefore does not have access to the same set of features.

What works and what doesn’t

Let’s assume that you have Snow Leopard and Exchange 2007 SP1. What works and what doesn’t? Based on my experience so far:

  • You will be able to connect on an internal network or VPN, provided that EWS is enabled, which it usually is. You may need to install a digital certificate to avoid warning messages.
  • Mail, Calendar (iCal), tasks and notes in your Exchange mailbox all appear nicely.
  • When outside the network, you will only be able to connect over the Internet if EWS is published externally, which it often is not. You cannot use RPC over HTTPS.
  • There is no access to public folders (note that these are deprecated, but still widely used).
  • It is not possible to send from an email address other than the default.
  • You cannot use Exchange delegation features, such as accessing other mailboxes.
  • Mail will download the entire mailbox; you cannot set it only to download recent items. There is no “online mode” as there is with Outlook.
  • When offline, you can access existing items, but new messages have to be saved as drafts. This is unlike Outlook, which gives you full access to send mail, delete etc, and synchronises on re-connect.

Snow Leopard vs Entourage

You might imagine that Microsoft’s own Entourage product would do a better job than Apple Mail at connecting to Exchange. This is not necessarily the case. The problem is that Entourage 2008 doesn’t use MAPI either. In its first incarnation it uses WebDAV. This proved so problematic that Microsoft quietly released a new Web Services Edition that uses EWS, like Snow Leopard. Even this is a temporary expedient, as the Mac Business Unit has announced Outlook for the Mac. The implication is that it will be closer to feature-parity with Outlook on Windows, though it’s not clear to me whether this means MAPI, or EWS, or who knows what?

My view is that unless you need some specific feature of Entourage, or find that Entourage mysteriously works where Snow Leopard does not, you are likely better off without it. This presumes Exchange 2007, of course. The fundamental reason is that Mail and iCal are nicely integrated with the operating system, whereas Entourage is not so good in this respect; there have also been quality issues with Entourage.

It would be good to see a detailed technical note from Apple and/or Microsoft on Snow Leopard’s Exchange support, how to configure Exchange for it, and any implications for security etc. In the meantime, there is an interesting discussion on Apple’s forums which highlights the issues.

For all its (many) faults, Outlook on Windows remains a better Exchange client than either Snow Leopard or Entourage.

Outlook HTML is better broken and safe, than rich and dangerous

The campaign at is brilliant. Outlook 2010 will have broken HTML support, it says, because it will use Word to render HTML:

Microsoft has confirmed they plan on using the Word rendering engine to display HTML emails in Outlook 2010. This means for the next 5 years your email designs will need tables for layout, have no support for CSS like float and position, no background images and lots more.

The web page hooks into Twitter and displays avatars from – currently – over 20,000 supporters.

Here’s a few things the campaigners do not mention. First, the Word rendering was introduced in Outlook 2007. It is not a new issue; and in fact caused some commotion last time round.

Second, using Word to render HTML is safer. Here is the bit of Microsoft’s response that matters to me:

For e-mail viewing, Word also provides security benefits that are not available in a browser: Word cannot run web script or other active content that may threaten the security and safety of our customers.

I recall endless security problems with embedded Internet Explorer in earlier versions of Outlook. I used to set Outlook to display as plain text; and even then there were scenarios in which IE could be exploited.

Third, I have no enthusiasm for emails laden with “rich” HTML, JavaScript, Flash and the like. These kinds of emails are invariably marketing and usually not worth reading. What is the “Email Standards Project”? It’s nothing to do with the W3C. The major sponsor appears to be Freshview, whose main product is Campaign Monitor:

Built just for designers, Campaign Monitor is 100% rebrandable email marketing software. Send campaigns for yourself, your clients or let them send their own at prices you set.

I am not averse to simple formatting in emails, for which Word is more than adequate. I agree that Word is not good as an HTML editor or renderer; but in this context it matters little – though I was even happier with the simple HTML editor Outlook used to have for those who disabled Word integration.

Therefore I am opposed to this campaign and suspect that many of the signatories have clicked with little thought or investigation.

That said, there is plenty wrong with Outlook. Dire performance issues in Outlook 2007; the most impenetrable user interface in general use; broken RSS support that fails to integrate sensibly with either Exchange or Internet Explorer; an archiving system that by default leaves users that have more than one PC with archives all over the place and in hard-to-find locations; and plenty more.

It would be great if Microsoft would fix Outlook; but not, please, by returning to embedded IE.

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Xobni: Outlook users should try this now

Yes, Xobni is brilliant.

Have you ever tried sorting an Outlook inbox by conversation? Of course Outlook goes into a thrash while it prepares the view. Then when it has finished, it does not work right. It has a limited view of what a conversation is, based on the email title. It does not show your sent items, unless you sort them into the same folder. In fact, it is more frustrating than useful, which is why I never use it.

Xobni (the name is inbox reversed) does this right. When you select an email, a panel shows your previous emails from that person, with your replies, which you can read without changing the focus from the message you are attending to. It is based on an index together with some simple analytics. Who else has appeared in the cc list on emails from this person? Where are their messages? What is the sender’s phone number? All of this information is shown automatically; no need to hit confusing menus like Arrange By or Current View.

There’s also a search box; it’s smoother and quicker than Microsoft’s desktop search, also used by Outlook in the latest version. Under the covers lies my favourite desktop database engine: sqlite. I’ve turned off the official Outlook search; anything to speed performance.

Xobni is free right now (it is a beta), so what’s the business model? Still up in the air, apparently. However, given the number of Outlook users, I expect it will be possible to monetize it. Apparently Microsoft tried to buy the company and was refused.

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