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Synchronizing Gmail, Yahoo or Hotmail with Outlook

October 21, 2009 by Jimson Lee

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I am irked because I got a Paypal annual renewal bill from Yahoo for $19.99, which makes up a fraction of their recent $1.575 billion dollar 3rd Quarter revenue.

So why am I paying for email when there are so many free ones?

Almost a decade ago, I needed a web based email program that offered POP/SMTP to download email on my local Outlook application.  At the time, I liked Outlook for it’s folders, coloured categories, and threaded conversations.  Plus, it gave me a chance to work offline in DRAFT mode, or simply use the store-and-forward mechanism once I was on-line again.

Outlook was the corporate standard at the time, so I could have all my different email providers piped into the same mailbox.  Colour-coded rules were used to differentiate the different emails.  Plus the calendar and contacts synched to whatever PDA device I was using.

Pre-2002 subscribers of Microsoft Hotmail could also download mail to Outlook Express (and later, Outlook) using the HTTP connector.  But they got rid of this and feature and soon was it only available to the paid Hotmail Plus subscription service.

Yahoo charged $19.99 per year for their premium services.  But it also offered more services, such as “disposable” emails with unlimited aliases.

In the time when someone else’s email got hacked and spammed to death, if you were on their mailing list or InBox, YOU would be added to the spam list!  That includes once-shot emails with Craigslist users, or whoever.  So instead of jimson@yahoo.com, you would use jimmy-craigslist001@yahoo.com.

If you signed up to a lot of newsgroups and listservs, then you could setup these aliases with folders and rules.  This is the reason why I still pay $19.99 per year for this premium service.  I am too lazy to change them.

Good News with MSN, Hotmail and Live Users

Microsoft lifted the “paid service” as of this year and now offers free POP/SMTP access.   You can also use the free Microsoft Office Outlook Connector, which provides several advantages over the traditional HTTP or POP3 connection.

The connector allows user to access and manage Hotmail account including email, contacts and calendars from within Outlook.

In Outlook, users can always apply another layer of Junk Mail filters (on top of Hotmail).

The Big Winner?

At the end of the day, Gmail appears to be the big winner.  It also offers authenticated POP/SMTP using non-standard ports.

The ultimate syncing tool is IMAP if you want full access to your InBox and Sent Items (downloading POP email only keeps dual copies of InBox items).  Just be careful if you have poor Internet connectivity.

Plus their Labs are always coming out with nifty tools and accessories.

And it’s all free.

After all, free is good.

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Written by Jimson Lee · Filed Under Jimson Lee, Technology & Security 

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