Design Flaws of Microsoft Outlook

Microsoft Outlook for Mac
version 15.36.1 to 15.40
  1. Voting
    If one complains about a problem, one is told to vote for the problem in a forum. Nothing is ever done about things listed in the forum so one quickly uses up all of one's 3 or so votes. Then one cannot even report a problem. The forum is useless. Issues should be addressed quickly and cleared rapidly.
  2. Rules
    The GUI for the Rules for blocking emails is badly designed on all levels:
    • THE ACTUAL ADDRESSES (with '@') ARE NOT DIRECTLY LISTED. So one can't immediately tell if one already has a rule! It takes 5 clicks on EACH RULE to determine the '@' address and it is impossible to see more than one at a time. Since they are not in alphabetical order, one has to fight to clean them up.
    • The GUI is tiny so it is difficult to manipulate and to see the big picture of the rules.
    • The GUI lists the Rules in an arbitrary order. One cannot make them list by time or alphabetic. So it is difficult to impossible to compare the rules for duplication.
    • Editing a Rule requires 4 to 5 clicks and so is extremely slow and awkward.
    • There is a maximum number of rules, about 50. After that one has to delete rules. But because of all the above design flaws, this is a laborious task.
    • Duplicate rules are retained instead of being detected.
    • One of my rules is ignored, so Rules doen't even WORK! The spammer keeps sending it and I keep adding it to my Rules - so there are now multiple copies (I think) ...
    • One can't make a rule for just the part after the '@' of an address. Spammers obviously know this so they first send you a email from Then they send you an email from etc. The rules then get filled up and the spammer gets to show you their spam every day.


    By comparison, editing of the Unix procmail control FILE is as efficient as your favorite editor. I use the super efficient vim and so can zoom around my rules, find things, see things and quickly change things. I have HUNDREDS of rules and procmail is still fast!

    Outlook's Rules design is hopelessly bad.

  3. To detect phishing, it is useful to see the source email address of all emails. The @ address is not immediatly shown in the GUI when one looks at an email. This is one of the easiest ways to detect spam and phishing AND OUTLOOK DOESN'T LET PEOPLE SEE IT EVERY TIME!!! Some emails show the source and others do not. I suspect the rule is that the ones similar to my address are hidden. That means that a phisherman only needs to simulate an internal email and they will be able to catch people. There are no options in "Preferences" for displayin full addresses all the time.
    SOLUTION: ALL emails should ALWAYS display the COMPLETE source address with the '@'.
    SOLUTION: Access to FULL original email headers should be a single click.
  4. Outlook is INCONSISTENT.
    • Next to the Junk mail box is a number representing the number of junk emails. This number can only be changed by removing the emails. No other mail box functions this way. It is bad design since it emphasizes the Junk mail!
    • When in one is in the Sent mail box, there is no option to archive the emails! One must drag and drop them in the Archive.
  5. Many controls take up space but are invisible! So people will not even know they exist unless they happen to move their mouse over the magical spot. This is a horrible design and should NEVER ever be done.
    Example: there are three invisible control icons on each email displayed, Trash can, Archive and Flag. These only show up when one is on the email.
  6. In the email processing Rules it is impossible to detect part of an email address such as or ''. The spammers know this and keep changing the first part of their address so as to get around Microsoft's bad design. Example: ''. Mail delivery agents that have real languages, such as the deprecated procmail or the newer maildrop (maildrop home) and sieve run circles around this bad design!
    Furthermore, mail rules do not function at all! They are ignored.
  7. There is a general inability to program Graphical User Interfaces (GUIs). So, as in the case of Microsoft Outlook, one cannot adjust how it functions to match one's work flow. The design is created by fiat and if it is bad the users suffer. Microsoft does not listen to design suggestions.
  8. Outlook apparently cannot be programmed to redirect email to another mail delivery agent. One is forced to drag and drop email to the desktop to get a copy. This cannot be automated (as far as I know). Because it is a GUI one cannot control Outlook remotely.
  9. Design suggestions are ignored by MicroSoft. There used to be an icon in the upper right corner ':)' that one could use to chat directly with Microsoft. This was removed and not replaced, making contact difficult. Previous discussion threads were lost. The people responding frequently don't read carefully and answer with useless boiler-plate responses.
  10. When Outlook receives an email with standard greater thans (>) on the left edge, which CLEARLY indicates quotation, the greater than is removed on the GUI display leaving a single space indentation. This makes it hard to see the quoted region. Worse, when one copies the email, even the space is gone, so the indentation notation is completely wiped out WHICH IS VERY CONFUSING! Why can't they just LEAVE THE EMAIL ALONE in the form INTENDED BY THE SENDER? 2017 Dec 03: I learned more about this. It turns out that if one captures the email outside OutLook by dragging and dropping it to the desktop, the '> ' is still there! So the effect is entirely in the display of a TEXT email! It is horrible design to modify a TEXT email without the user knowing it when displaying. This seems to be yet another example of Microsoft trying to be helpful and just getting in the way. (Remember the famous paperclip?)
  11. The help access has multiple problems:
    • It doesn't provide a way to have multiple tickets!
    • It doesn't provide a way to close a ticket on the user's end!
    • One can't see all the tickets either open or closed at once!
    • There is no record for the user. It would be better to communicate by email so the user has a record. (Note: 2017 Nov 13 13:03 they promised to work on this.)
    • For my records, I want to to capture the help thread text into a text file. One can only cut/paste individual statements. The date/time of each statement is lost. With a thread of 50 comments one would have to capture each statement individually and RETYPE the date/time stamps!


  1. When I preview multiple PDFs in an email, stepping forward and backwards through them hangs this horrid piece of software. Repeating the same steps and it works. Flakey.
  2. If one adds a rule for something already in the blocked list Outlook CRASHES (sometimes).
  3. Loss of connection. I left my computer connected by VPN for more than 5 hours. During this time the VPN remained functional. Also, I opened an ssh link through VPN and that was not broken. However, Outlook reported losing contact. It cannot be VPN since the ssh link and VPN are still running. So Outlook somehow fails. I quit OutLook and started it again - and it was fine.

color bar Small icon for Theory of Molecular Machines: physics,
chemistry, biology, molecular biology, evolutionary theory,
genetic engineering, sequence logos, information theory,
electrical engineering, thermodynamics, statistical
mechanics, hypersphere packing, gumball machines, Maxwell's
Daemon, limits of computers

Schneider Lab

origin:    2017 Aug 02
updated: 2017 Dec 05

color bar