Outlook 2016 attachment mysteries and annoyances

Microsoft Outlook 2016 has a new feature which the company highlighted when it first appeared, which is that it sends attachments as links by default, if they are stored in network-accessible locations. The idea is to prevent proliferation of different versions if several respondents make changes and email them back. It also means that everyone has the latest version. Good stuff, right?

I am not sure. Of course Outlook is meant to give you the choice about whether to send as a link or as a copy, but we all know that busy people just click and expect it to work; they mostly will not think through which method is appropriate in a particular case, or in some cases, even understand the difference. One of the implications of sending links is that the document received may not be what is sent. For example, consider this scenario:

1. Hmm, shall I send the minutes of our last meeting to this person at supplier X? Better check there is nothing sensitive in it. [Checks]. OK, send.

2. Colleague happens to look at minutes, thinks, why did we not minute our difficulties with supplier X? Adds section of sensitive information and proposal to switch to supplier Y.

3. Person at supplier X receives document …

OK, my scenario is somewhat contrived, but you can see the underlying issue.

There is also the question of whether the mechanism behind this feature is really robust. It is not in fact a simple feature. What is meant to happen is that Outlook detects whether your document can be sent as a link, and if it can, interacts with SharePoint to create a magic link with either view or edit permissions. In my experience, it is easy to end up sending an attachment that cannot in fact be accessed by the person at the other end.

I have an internal SharePoint and soon figured out that I had to prevent Outlook from sending documents as links. The URL I use for SharePoint internally is not accessible externally, which is perhaps a flaw in my setup, but not one that has ever caused problems before. In any case, I would prefer not to give out any magic links to documents in my SharePoint; it just seems an unnecessary security risk.

In the case of Office 365, note that external sharing may be switched off, in which case links will not work. External sharing may also be disabled for specific sites.


Maybe Outlook 2016 is smart enough to detect whether or not external sharing is enabled, but if so, this does seem to go wrong sometimes. I have seen cases where users send an attachment link, but the recipient cannot access the document. Rather, they click the link and get a “can’t be found in directory” error or similar.


Another issue is that Outlook 2016 does not always offer you the choice of link or attachment. Here is how it is meant to work. What happens sometimes though is that the attachment does not end up in the “attached” header at the top of the email, but rather in the body. In this scenario, you actually end up with a small Word table (Outlook messages use the Word editor) that cannot be converted into a standard attachment:


Note the little icon, an embedded image, which includes a cloud to give you a clue that this is not really attached. It also seems to mess up text formatting; note that my typing is now Times New Roman rather than Calibri. Another Outlook mystery.

This problem only seems to happen if you select a file from Outlook 2016’s recently accessed document list, which appears when you click the new Attach File button:


So how do you prevent this behaviour? Given the difficulties it can cause, I thought Outlook might have an option to disable sending attachments as links, or at least to prevent it happening by default. I have not found such an option yet. One point to bear in mind is that in previous versions of Outlook it was not easy to send a document from SharePoint at all, unless you could access it from Windows Explorer. This means using WebDAV (“Open in Explorer”), or the still-problematic OneDrive for Business client. So the dropdown with recently accessed SharePoint and OneDrive documents is new and potentially welcome functionality.

Here are a couple of workarounds though. If you format an email as plain text, which you can set as default if you choose, then you will not get the embedded link that cannot be changed. Instead, you will get the dialog with options to link or attach a copy:


What if you want Outlook 2016 to behave like Outlook 2013 and earlier? Well, the Attach File with the dropdown is not customizable directly, but you can add an old-style Attach File button. To do this, start a new email, right-click the toolbar, and click Customize the Ribbon. Right-lick the New Mail Message section on the right, and choose Add new group. Then select the Attach File command on the left, and the new group on the right, and click Add. I have called my new group Custom:


The effect is that you now have two Attach File commands, one of which behaves just like Outlook 2013:


My custom Attach File is on the right in the image above, does not have a drop-down list, and simply selects a file using an insert file dialog.

I appreciate that these are workarounds and not complete solutions.

Did Microsoft really think through this feature? Why the bugs? Why no easy way to disable it? I wish I knew.

Microsoft Office 365 and desktop friction

Microsoft would like us to think of Office 365, its hosted email and collaboration service, as “cloud”. And it is in many ways; you can even get all your email and Onedrive-stored documents direct from a web browser.

The truth though is that Microsoft has been careful not to disrupt its desktop Office software too much. Most users, in my experience, choose Office 365 in part because of its integration with Outlook, Word and Excel. You can install the software from the Office 365 portal, and open and save documents from Onedrive for Business.

Another part of the service is online chat and conferencing, for which you need the Skype for Business (formerly Lync) client on your PC.

There is an issue here though. Part of the attraction of “cloud” is that you do not have to manage software; but in the case of Office 365 you do have to manage the software that is installed on your PC. Microsoft’s investment in click-to-run installation has helped to simplify the setup, but under the covers it is as complex as ever.

Take the case of a small business I know, which was on the Office Midsize Business plan. Microsoft has retired this plan, so when it came to renewal time the customer had to change to a different plan. If they wanted to keep *all* the features of Midsize Business, including the Access database app, they could migrate to the Enterprise E3 plan – at £14.70 per month, nearly double the £7.80 per user/month for Midsized Business. On the other hand, they could migrate to the Business Premium plan for the same cost and, well, *nearly* the same features. The horrible details are here.

They didn’t use Access so Business Premium seemed OK. On the cloud side, the migration was straightforward. However, since Access was no longer included they had to remove and reinstall Office, as well as the Skype for Business client.

In this particular small business, most of the users needed some assistance with this operation. Unfortunately there is no single button to click that will remove the old Office and install the new one. You have to remove Office using Control Panel, then reinstall it from the Office 365 portal. Removing Office removes the old Skype for Business client, but putting it back means choosing a separate installation option in the portal, which most of them missed. One user somehow ended up with two versions of Office 2016 installed, neither of which worked properly. Office would not activate, reported an error, and offered to repair itself. This was not going to work, since it was the wrong version of Office.

Even when it goes smoothly, the business of removing Office and reinstalling both the desktop software and Skype for Business takes a long time, over an hour.

Overall, life in the Office 365 era is easier than it was in the days of 27 Office floppies, one or two of which were bound to be unreadable. Nevertheless, it is friction, and not fulfilling the seamless promise of cloud.

New Delphi and C++ Builder Roadmap promises Linux server support

Embarcadero has published a new roadmap explaining what to expect in forthcoming editions of its RAD Studio suite, including Delphi and C++ Builder.

The company has been acquired by IDERA though the Embarcadero brand is to continue under the new ownership.

The roadmap covers two “development tracks”, though it is not completely clear what that means. One is described as the “Spring development track” which suggests a release in April, 12 months after RAD Studio XE8. However, the post adds that “The team is working the following features that will be included in 2016 releases,” raising the possibility that some features in this track may come later, perhaps in the scheduled summer update.

The Spring track, to be called “Berlin”, seems to be mainly a tidying-up exercise in any case, with features including Bluetooth LE support for Windows 10, DirectX 12 support, native support for Utf8String on all platforms (you mean it does not have this already?) and enhancements to the FireMonkey cross-platform framework.

“Spring” also offers C++ CLANG 3.3 on all platforms.

The second development track “will deliver a Fall release”, to be known as “Tokyo”, following the pattern of recent years where RAD Studio has two major updates every year. The Fall track is more interesting, and includes support for Delphi and C++ Builder on Linux Server, as well as “Linux platform support for console apps with IoT support.” I guess non-GUI Linux is the common thread here.

The IDE will remain on Windows, with cross-compilation for Linux. Initially supported distributions are Ubuntu Server and RedHat Enterprise, though further distributions will be added “as demand dictates”.

It is good to see Linux support back in Delphi. I remember Borland Kylix (2001-2003) well, but this was back in the days when desktop Linux looked like more of a thing.

The feature-list for Tokyo also includes Windows Centennial support. This is potentially big news. Centennial is a Microsoft project to deliver Windows desktop applications through the Windows Store, using application virtualisation based on the existing App-V technology to remove dependency issues. You can expect to hear more about Centennial at Microsoft’s Build conference at the end of March; it was covered at last year’s Build but we have not heard much more about it since.


Embarcadero is also promising a new installer for RAD Studio, based on its GetIt technology, which will reduce installation time and give more flexibility in selecting features. This would be welcome; I never look forward to installing RAD Studio as it tends to be a time-consuming process. It would also be good if it messed less with system environmental variables, though I do not know if this is on the cards. The new installer will comes in two phases, phase 1 in Berlin and phase 2 in Tokyo.

My own view is that two major releases a year is one too many, so I would prefer if Embarcadero scrapped Berlin and went straight to Tokyo.