Email woes, Live Mail and Outlook

Windows Live Essentials was released in 2012. Basically, it included an email client that was Outlook Expresses replacement. It had other features; however, Mail is the one I want to write about.

Windows Live Mail (WLM) allowed you to create folders, sub folders, link your contacts and calendar together. While many other programs allow this, WLM was nice because it was:

A Microsoft product


It kept all emails and folders in a file structure you could see in Windows Explorer.

In January 2017, Microsoft quit supporting Windows Live Essentials and thus stopped downloads for it.

For years they have included a free mail client in Windows 8 and 10. They don’t do half of what WLM could do. If you tried to migrate from WLM to just Mail, in my experience, you would lose most of your file structure and the ability to send group emails. If you had a Christmas card group, a wholesaler’s group and a business networking group, they were lost (the group, not individual contacts) in the migration. I also experienced the loss of many emails, both old and new. In my last attempt to migrate for a client. Specifically, all emails from 9/10/17 to 10/12/17 (when I tried the migration) did not make it, as well as all emails prior to February 2017.

Because WLM kept a file structure, if an email became corrupt, only that email was corrupt. It also meant that if you needed to transfer data (emails) to a new program, all you should need to do is point to the main folder containing your emails and all sub-folders would be imported.

After spending numerous hours trying to get all of my above customers emails into the Window 8 built in mail program, I gave up and tried is the online version and NOT the same as the desktop version of Outlook. It is what used to be

With I was able to get all the emails to be seen, not really an “import” so to speak. It took about 24 hours for the contacts to migrate over (there were only 250).

The advantage of is that it is online, so no matter where you are or what you have with you, you should be able to access all your emails. Being online is also its disadvantage. If you don’t have internet access, or if it is slow then you will have issues accessing your email.

I ran into another BIG issue with this clients’ email transfer. This customer had a Windows 7 PC with the exact same security software, setup the exact same way as on the new Windows 10 PC. Opening on the Windows 7 machine was fast and never a hiccup, even though the internet at that office is only 6 Mbps up and usually runs at 1.x to 2.4 Mbps down. The Windows 10 machine timed out and hung constantly. If I went 3 feet over, opened it on the Windows 7 PC, everything worked.

I switched the LAN cables between the two computers, no change.

Before you go with the “remove your security software” statement, shut your mouth and open your ears. That is NEVER an acceptable answer. In this day and age, any software vendor that says that is a FOOL, period, end of story.

It is my understanding that there is the ‘free’ and then, if you have office 365 a different online version. Unfortunately, all links and information from Microsoft and Google both pointed me to the free version. This customer does have an active 365 account.

Did I mention the free version, or in this case the only version, has ads that are either on the right side or bottom of your browser when reading email? Well it does.

So why not use the desktop version of Outlook? Well, first the customer constantly stated “I hate Outlook” over and over and over. In their mind, it was no good.

I use the desktop version Outlook, and overall, I like it. There are some issues such as all your data (emails, contact, calendar, notes et al) are in one big file. Either a PST or OST file. If one part is corrupt your whole email / contacts / calendar are in jeopardy. You might know about the built in “scan PST” program that ‘fixes’ corrupt or broken PST files. That is all find and dandy on two conditions. First, if it can repair the file, if not your hosed and all data that was not backed up before the corruption is lost. Second, if you use IMAP instead of POP3, you have an OST file and there is no repair tool for it.

Yes, there are 3rd party programs that repair or rebuild both PST and or OST files. I have had to use them in the past. It would be just a lot nicer if each file or at least segment (emails, contacts, calendars, file structure, notes) were different files, not one giant 12.8 Gb file. When you open such a large file, it takes a while.

A quick review of what is available from Microsoft.
Windows Mail
Pros: Free, Quick
Cons: No grouping of contacts for emails, Very poor and low level of file folder creation.
Thoughts: It is good for individuals who only use email because they have to.
Pros: Free, Online, when you access it, you are getting your email, no matter what internet device you are using.
Cons: Ads, it depends on an internet connection, no internet no email, Issues accessing with different computers, time outs et al

Outlook, desktop
Pros: resides on your device, with our without internet you can see your current data
Cons: One large file, if something happens to it, everything is in jeopardy, More difficult using across devices. While you can setup IMAP, sometimes “sent” items from one computer do not show up under “sent” items on the different device. One large file slow down opening the program, navigating through the program. Size does matter. Not free. Can be bought by itself for about $110 or as part of Office 2016 home and Office, Office 2016 Professional or Office 365.

Until we meet again, have a virus free week.

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