For a while now, I’ve been thinking about switching from Gmail to Outlook.com as there are so many features in Outlook which Gmail can’t support because it is using IMAP.

For instance, synching my Contacts and Calendar folders, synching my message rules, using Categories and Follow Up Reminders, Skype Contacts integration and so much more.

I’ve been quite reluctant to actually switch as nowadays so much depends on and is connected to your email address, it feels like I’m tied for life to use Gmail.

How can I switch from Gmail to Outlook.com as painless as possible?

I do a lot of typing so I try to use the mouse as little as possible as it breaks my flow. I also found that using keyboard shortcuts is often much quicker than using a mouse.

In Outlook, I have multiple accounts configured but I have not yet found out how to switch between the accounts when composing an email.

Is there an easy way to select the sending account via a keyboard shortcut?

As a delegate for my manager, I sometimes also need to create Private Appointments. However, I do not have the permissions to see any details of his existing Private Appointments.

But when I’ve been set up as a Delegate without permissions to see Private items, the button to mark an appointment as Private is grayed out as well.

Is there a way to be granted this level of permissions without losing the option to mark appointments as Private?

I’ve configured my Outlook.com account with multiple aliases. When I use the web based version of Outlook.com, I can successfully send out an email with one of my alias addresses.

However, when I specify an alias address in Outlook, it still only sends from my primary address.

How can I send out an email with one of my alias addresses for my Outlook.com account in Outlook?

I’m having a problem with emails being returned from people I’ve been in contact with for years and I’m very sure they didn’t all just change addresses or that I misspelled them. The error I get is;

550 mail.server.com ESMTP
Connection rejected. Your IP xx.xxx.xxx.xx is in RBL

What does this error mean and how do I fix this?

I’m Categorizing specific items in my Calendar, Contacts and Tasks folder. For instance, in my Calendar and Contacts folders, I’ve made a distinction between Work, Private and Sport Club.

Sometimes, I want for instance to print out my Work Calendar schedule or a list of Contacts to hand out to a new member of our club or just my list of Garden chores to hang outside.

While it is easy enough to categorize them, I have gone through all the printing options, but can’t find a way to select which Category to print.

How do I print just one Category?

In a previous tip, you mentioned that it is not recommended to store pst-files within Cloud based storage folders like OneDrive or DropBox.

I still have lots of space left in my OneDrive and DropBox accounts but not a lot of space left in my mailbox.

Is there really no way I can use all this space to archive my emails to the Cloud?

When I switch to the Calendar Navigation (CTRL+2), I see multiple Calendars listed for the various accounts that I have.

However, new meeting requests which I receive do not always get added to the Calendar of that account.

For instance, meeting requests I receive for my personal POP3 account get added the Calendar folder of my Exchange account from work.

How can I set the default Calendar to be the one of my POP3 Calendar?

I’m multilingual and frequently type emails in English, Dutch and German. I’ve installed everything on my computer in English and when I type an email in Outlook on the Web, the English spellchecker kicks in when needed.

Unfortunately, Outlook on the Web doesn’t seem to recognize when I type in Dutch or German.

How can I add additional languages to Outlook on the Web?

Lately I’m having some sync issues with my mailbox. For instance, I see several new emails in my mailbox when I login to webmail which I don’t see in Outlook.

Also, it looks like the entire month of June has gone missing in Outlook but the emails are luckily still available on the server.

Is there any way to get Outlook to sync or download these emails again?