Email client shoot-out: Outlook.com and Gmail

Set up email filters by sender or by topic. For example: email from Marvel comics always skips the inbox and ends up in a folder titled "Marvel" or skips the inbox and gets tagged "Marvel." Or email from Bill Gates goes to a folder titled "Supreme Leader."

Can Gmail do this?

Yes.

Can Outlook.com do this?

Yes.

How?

Select an email recipient. Then, choose "Filter messages like this" from the drop-down menu. You can then select additional parameters for these messages, like telling it to skip the Inbox or only adding it to the label if there's an attachment or certain key words.

You can color code the labels so they're easier to find, which also match with how they're displayed in the Gmail mobile app for iOS and Android.

How?

Yes - there are multiple methods to access this feature.

Set up canned responses or automatic responses so you don't have to type the same response (or C&P it) again and again.

Can Gmail do this?

Sort of.

Can Outlook.com do this?

Not really.

How?

This functionality exists from the vacation responder. You can select a message that is automatically emailed to contacts who email you in a specific time period. You can choose to only send this reply to those in your contacts list.

How?

You can set up a vacation responder, but you can't specify whether or not that response only goes to your contacts — it goes out to everyone.

Set up an email alias for a group of people for quick and easy typing later (So you don't have to keep remembering all eight email addresses for your comic book club).

Can Gmail do this?

Yes.

Can Outlook.com do this?

Yes.

How?

Sign in to the Google Apps Admin console. Then, Click Groups. Select the group you want to add an alias to. Click Aliases, click Add an alias, specify an alias in the text field. Click Save changes.

How?

First, click on the grid icon in the top left corner of the Outlook.com inbox page and then click on the People tile. Click on New on the action bar and then click New group from the dropdown menu. . On the Edit group page give your email alias a name and then add members from the drop down. Note: You must already have the group members added to your People group in order access them in the drop down. Click on Save to create your new email group alias. You new email group alias will now show up in searches when you are adding people to your email draft.

Integrating email with calendar: Can you easily add meetings/commitments to your calendar from an email message? The flip side: Being able to mail calendar-based notifications to yourself and others from within your calendar.

Can Gmail do this?

Yes.

Can Outlook.com do this?

Yes.

How?

Add meetings: You can accept an invite from most calendar programs: just click accept and it goes into your Google Calendar.

Or, if you use Chrome add the Google Calendar extension. This turns most text that contains a date into a clickable entry. Then add it to the calendar.

Invites are also handled from Google Calendar. The program will auto-suggest names based on your contact list. Calendar events will also appear in your Google Now feed if you've enabled the feature.

How?

E-mails received with a meeting in them can be added to your calendar. However, notifications & reminders can only be sent to the originator of the meeting, not all participants.

Search: How easy is it to search folders/email archive by: person, subject line, keyword? I'm thinking about how easy it is to set up specific searches by filter (say you filter for the keyword "Marvel" and the sender "Dr. Doom"), in addition to how easy it is to search by message status (unread, for example).

Can Gmail do this?

Yes.

Can Outlook.com do this?

Yes.

How?

Google's search prowess is one of the best reasons to use Gmail. You can specify search topics by person, keyword, subject line, label, or several other different specifications. Additionally, once you create such a search you can turn it into a filter, so future messages are always available according to that criteria.

How?

Your emails are searchable and customizable, but your searches can not be saved for future use. Advanced search lets you set multiple filters on the search, like recipient or subject line. Search results can be further narrowed down on the fly by clicking on any one of the headers in the main content panel that contains the search results. Those headers allow you to narrow down by folder; category; attachments and a range of dates.

Extensions and add-ons: Does the service have ‘em? What are the most useful ones?

Can Gmail do this?

Yes.

Can Outlook.com do this?

Not yet.

How?

Gmail has numerous add-ons. If you're a Dropbox user, you'll find the official Dropbox extension quite useful as it allows you to click the Dropbox icon and throw in any files that are stored in your cloud. Another essential option is the Offline Gmail web app, which allows you to work on your inbox even if you're disconnected from the Internet.

How?

Extensions are in Preview right now so not all accounts have it.

Alerts: Can you control the visual and audio alerts that tell you when you have mail?

Can Gmail do this?

Yes

Can Outlook.com do this?

Y/N

How?

You can enable desktop alerts by going to Settings > Enable desktop notifications. You have a small amount of customization - you can get alerts for all messages or only those that Gmail deems "important" based on following your usage patterns.

How?

TK5

Customization? Can you easily change the look/feel of the user interface so it's just what you want it to look like?

Can Gmail do this?

Yes.

Can Outlook.com do this?

Y/N

How?

There are numerous themes to skin Gmail - some created by Google and others from the user community. You're also able to upload your own image to serve as the background.

You can also tweak how tight the interface is: comfortable, cozy, or compact. Turn on the social, promotions, updates, or forums.

Finally, you can also use Inbox by Gmail. It bundles up messages by common type, and lets you snooze them away like Dropbox's Mailbox app. If you like this style better, you can also use the Inbox app for iOS and Android.

How?

TK5

Customization part II: Can you easily change the look/feel of the emails you're composing and sending? Can you save that look and feel? Can you save templates? Or .sig files?

Can Gmail do this?

Sort of.

Can Outlook.com do this?

Y/N

How?

There are not as many choices here.

How?

TK5

Multiple email addresses: Can this email client handle receiving and sending email from different email addresses? How easy it is to set up the email client to handle receiving email from different addresses? How easy is it to switch between different email addresses when you want to send email? (Most importantly: When you read an email in one account, will your reply be sent by that account or is there a default account you'd have to switch out of.)

Can Gmail do this?

Yes.

Can Outlook.com do this?

Y/N