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How to Migrate Windows Live Mail

jparker402

jparker402

macrumors 6502a
Original poster
Jun 7, 2016
588
60
Bellevue, NE
New to all of this. Can't operate my new MacBook Air yet, but need to plan how to migrate my Windows Live Mail to the Mac email system. So far have not had many good leads. Did find one program I could buy that apparently will transfer files (wherever they are in my Windows) but apparently won't transfer contacts. I have not talked to my email provider yet, but in previous conversations I think they are mostly involved with settings. Another thought that just flashed in front of my mind (always dangerous) is to try to upgrade Live Mail to a higher grade Microsoft program and then transfer it. Would appreciate any help/direction anyone can give. Figure someone here has run into this situation before. Thanks!
 
jparker402 said:
Not sure I understand the first set of instructions. As to the second, I have Windows Live Mail, not Windows Live Hotmail. There is apparently a difference.
Click to expand...
Windows Live Mail is an email client used to access email accounts. Windows Live Hotmail is an email host/provider, being ported to Outlook.com Cloud Services.
http://answers.microsoft.com/en-us/...and-live/8d10dfe9-d61a-44a1-b18d-18e714a5719f - note the clarification by an MS Mod.

MS is porting the entire Outlook.com Cloud Services backend to the same system as Office 365. I use both Outlook.com (and can still login with my Live username) and Office 365.

Regarding moving to the Mac, there are issues with synching mail and contacts to the Mac apps, and they're long-standing issues going back several years. MS has promised - in their roadmaps - fixes to these synching issues, but I'm not going to hold my breath. A significant issue with Mail is delayed synchronization - Outlook.com's recent move to fully EWS will likely further complicate email synching between MS's products and non-MS clients; I find this a bit aggravating as I can make significant backend settings changes to my iCloud accounts directly from Outlook 2016 for Windows and the installed (Windows 10) Mail app. The Mac Contacts app has long had sync/timeout issues (largely related to resolving Categories), pretty much going back to Day 1 - with Exchange Servers (I own a Server 2012 license), Office 365, and Outlook.com, and only MS can fix this.

My solution is to use Outlook 2016. It works. I've learned to use Outlook with MS products, Airmail or the Gmail web interface with Gmail, and the Apple clients with Apple services - each provider uses different data fields, and each provider keeps changing their backend. I'm done fighting that battle, and I've had zero issues since I switched to using this workflow.

An alternative? Sign up for a free month of Office 365, download and install a copy of Outlook 2016 and sync it to your MS account. Wait for a bit. Drag all of your contact/calendar data to a place on your Mac. Set up an iCloud account, then import the contacts and calendars into your new iCloud account, then set up Mail to to talk to your MS account. I find this to be too much of a PITA - Outlook.com/Live Mail uses a completely different data format than what Apple defaults to, and I can pretty much guarantee your data will get bunged up sometime in the future. Outlook (the desktop app) fixes that headache for a lot less coin than a couple of hours of therapy... Cheers!
 
campyguy said:
Windows Live Mail is an email client used to access email accounts. Windows Live Hotmail is an email host/provider, being ported to Outlook.com Cloud Services.
http://answers.microsoft.com/en-us/...and-live/8d10dfe9-d61a-44a1-b18d-18e714a5719f - note the clarification by an MS Mod.

MS is porting the entire Outlook.com Cloud Services backend to the same system as Office 365. I use both Outlook.com (and can still login with my Live username) and Office 365.

Regarding moving to the Mac, there are issues with synching mail and contacts to the Mac apps, and they're long-standing issues going back several years. MS has promised - in their roadmaps - fixes to these synching issues, but I'm not going to hold my breath. A significant issue with Mail is delayed synchronization - Outlook.com's recent move to fully EWS will likely further complicate email synching between MS's products and non-MS clients; I find this a bit aggravating as I can make significant backend settings changes to my iCloud accounts directly from Outlook 2016 for Windows and the installed (Windows 10) Mail app. The Mac Contacts app has long had sync/timeout issues (largely related to resolving Categories), pretty much going back to Day 1 - with Exchange Servers (I own a Server 2012 license), Office 365, and Outlook.com, and only MS can fix this.

My solution is to use Outlook 2016. It works. I've learned to use Outlook with MS products, Airmail or the Gmail web interface with Gmail, and the Apple clients with Apple services - each provider uses different data fields, and each provider keeps changing their backend. I'm done fighting that battle, and I've had zero issues since I switched to using this workflow.

An alternative? Sign up for a free month of Office 365, download and install a copy of Outlook 2016 and sync it to your MS account. Wait for a bit. Drag all of your contact/calendar data to a place on your Mac. Set up an iCloud account, then import the contacts and calendars into your new iCloud account, then set up Mail to to talk to your MS account. I find this to be too much of a PITA - Outlook.com/Live Mail uses a completely different data format than what Apple defaults to, and I can pretty much guarantee your data will get bunged up sometime in the future. Outlook (the desktop app) fixes that headache for a lot less coin than a couple of hours of therapy... Cheers!
Click to expand...

Please bear with me because I am not very smart about all this. I tend to do things like this once every ten years, then promptly forget what I did.

My ISP is a company called Windstream; at least that is where my internet service comes from as well as my "email". I put email in parenthesis because I do not use Windstream's "program". I physically view my email using Microsoft Live Mail. I happen to like it better. I have not contacted Windstream about my new Mac, but I will. Have a feeling that they will not be any help in transferring data from Microsoft to Mac.

I have just taken a brief look at emails that I have filed over the years, and there aren't that many that are really necessary. I already have an iCloud account (as well as OneDrive), and I do have Gmail on my iPhone, if that makes any difference. If there is a trial version of Office 365 I would be willing to try that, as well.

Appreciate the thoughts. Please keep them coming. Am going to be "off" for a few days for my mother's 99th birthday. During that time I hope my brother will teach me the basics of the Mac, like copy and past, and how to find and download programs.
 
satcomer said:
Windstream Email Sever Settings
Click to expand...
Thank you, satcomer. I did get a chance to speak briefly with a Windstream tech rep today. Didn't actually start anything because of lack of time this afternoon. However, the rep did tell me that with Macs one doesn't use the POP "thing", and that there is/was a method of importing and exporting Windstream email files to iMail (which the rep said was Apple's email). After I learn a bit more about operating the Mac, I will definitely be in touch with Windstream to see how this all works.
 
jparker402 said:
Thank you, satcomer. I did get a chance to speak briefly with a Windstream tech rep today. Didn't actually start anything because of lack of time this afternoon. However, the rep did tell me that with Macs one doesn't use the POP "thing", and that there is/was a method of importing and exporting Windstream email files to iMail (which the rep said was Apple's email). After I learn a bit more about operating the Mac, I will definitely be in touch with Windstream to see how this all works.
Click to expand...

Here is an example for El Captain Mail Set Up Email on El Captain.
 
jparker402 said:
Please bear with me because I am not very smart about all this. I tend to do things like this once every ten years, then promptly forget what I did.
Click to expand...
No worries, and no need for bearing. We're here to help...

I use the Business version of Office 365, which includes Exchange-based email/calendars/contacts - but you don't need that. What I also do with the Outlook apps (Win/Mac) is add my Outlook.com email accounts and access them on both OS platforms - Outlook.com (nee Hotmail) works so much better with the Outlook app (gawd, I wish MS would have picked different names for the Outlook apps/email services - :mad:). All you'll need is the Personal or Home version of Office 365 - you get Outlook, which works with Hotmail/Outlook.com just fine. The 30-day trial is the Home version, and you can change to any of the non-business versions any time during that 30-day period:
https://products.office.com/en-us/try

I bought my Office 365 license from Best Buy, which matched Amazon's price at $65 for a year of Home. I bought two licenses at that price, since they're "stackable". I then use Office 365 Business Essentials for email/contacts/calendars since I don't need any more installs of Office for myself. Cheers!
 
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