In Thinking About Email Consolidation Strategies, I barely touched the surface of a complex, time consuming project in which I'll be consolidating several email services--along with their associated contacts, calendar items, and tasks--into a smaller, more manageable group. While writing that article, and again upon viewing the feedback, I've come to understand that this is something I may never effectively master, let alone communicate well enough to help others. But I'm going to give it a try. And in this second article, I'll take the next step, which is to move beyond abstract ideas and towards a more mechanical how-to. More specifically, I'll examine how you can use one email service to collect email from another email service.

To keep things simple, I'll focus on two of the most popular (and free) email services, Microsoft Hotmail and Google Gmail. Of course, this general process will generally work with almost any email services, including Microsoft's Office 365-based Hosted Exchange. Only the details will vary from service to service, as will the actual capabilities. (With my work-based Exchange 2010 account, for example, I cannot collect email from other services or forward email from that service to other accounts. This was determined by a corporate overseer using Exchange's group policies.)

So, in this example, we'll be using one Hotmail account and one Gmail account. For whatever reason, we'd like to manage all of our email from a single account. (And we'll examine doing so in both directions.) Regardless of which account you choose as your "main" account, there are two ways you can do this. You can collect email from a secondary account using a main account. Or you can forward mail from a secondary account to a main account. And while both methods provide similar results, they're not entirely identical.

Collecting mail from another account. When you do this, your main account is configured with your secondary account's logon information and it will periodically poll your secondary account for new email and then display that mail in your main account's inbox (or another folder). This method requires your main account to access the secondary account through a common email mechanism--typically the POP3 protocol--so you may need to enable that on the secondary account first.

The primary advantage of this method is that it will typically allow the main account to act on behalf of the secondary account. This includes sending new email that appears to come from the secondary account, and replying to email sent to the secondary account as if it were coming from that secondary account (usually automatically). But if your secondary email doesn't provide POP3 access, you may need to forward that mail instead.

Forwarding mail from a secondary account to your main account. Here, you configure the secondary account to forward any incoming email to your main account. The advantage here is that it happens automatically as mail comes in, so depending on the speed of your main account's email collection, this could actually be more immediate. (Some email services don't let you configure how frequently to check for mail at secondary accounts.) The disadvantage, however, is that you lose the ability to automatically act on behalf of the secondary account when accessing forwarded mail (and sending new mail) from the main account. That's because the main account has no real understanding of where your email has come from. (You can still separately and manually configure most email accounts to send mail as if it were coming from a different account. I'll discuss this process in the next article.)

Generally speaking, I recommend trying the first method, where you collect mail from another account, first. If that doesn't work, or the email collection seems egregiously slow, you can experiment with email forwarding instead. But if you don't care about replying to email with a secondary account, email forwarding works just fine.

In this article, we'll examine the first method, email collection. In the next article in this series, I'll look at email forwarding.

Collecting Gmail-based email from Hotmail

In this scenario, Hotmail will be the main email account and Gmail is the secondary account. You will use Hotmail to collect email that was originally delivered to Gmail.

To collect your Gmail from Hotmail, you'll need to first ensure that POP3 access is enabled in Gmail. At the time of this writing, you configure this setting from Options | Mail Settings | Forwarding and POP/IMAP | POP Download from within the Gmail web interface.

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You have two settings to configure here. First, you'll need to enable the POP protocol, and you have two choices, which amount to "for all mail" (i.e. include all of the email that was previously delivered to Gmail) or "for mail that arrives from now on" (i.e. excluding all of the previously delivered email). After choosing one of those methods, you'll need to determine what Gmail does with email that is collected from the primary (Hotmail) account. There are four choices: Keep Gmail's copy in the inbox, mark Gmail's copy as read, archive Gmail's copy, or delete Gmail's copy.

Looking at my own needs, I would elect to only deliver new messages from Gmail to Hotmail because of the absurd amount of email I've received over the years. (Though I will be looking separately at backing up my Gmail-based email archives later.) And I would choose to archive Gmail's copy, since that will ensure I have a second copy of any Gmail-based mail, and it won't clog up the Gmail inbox. Your needs may vary.

Whatever you choose, click the Save Changes button at the bottom of the page when you're done.

In a separate browser window or tab, logon to your Hotmail account. Select Options | More Options | and then Sending/receiving email from other accounts (under the section Managing your account). Click the link titled Add an email account.

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In the provided form, enter your Gmail address and password and click Next. (There is an Advanced options link that will let you configure server settings manually, but this isn't necessary for Gmail.)

Hotmail will attempt to configure the account. When it's done, you'll be presented with a second page in which you can configure where Gmail-based email will be delivered. You choose from existing folders (like the Inbox, which I personally prefer) or create your own folder. You can also colorize these Gmail-based emails so that they are visually distinct from Hotmail-based email.

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When you're done configuring these options, click Save. Hotmail will configure the email collection and then return you to the Hotmail inbox.

There's one more step to endure before this email management solution is complete: You need to reply to a verification email that Hotmail sent to your Gmail account. This ensures that you're actually who you say you are, of course. If you return to Gmail, you will see (or will soon see) an email titled Windows Live Hotmail: Verify your email address. Open this and click the provided link. Once you do so, Gmail will allow Hotmail to collect your email.

You may also want to revisit the Sending/receiving email from other accounts area in Hotmail Options. (Remember, it's in Options | More Options | and then Sending/receiving email from other accounts). Now, you'll see that Hotmail is configured to collect email from Gmail. You could also choose to collect email from more accounts or, if you wish, to remove the Gmail account you just attached.

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Also, when you send email from the Hotmail web interface, the From address has a drop-down symbol next to it, indicating that you can change from "From" address, on the fly, to any configured account. In this case, that will include your main Hotmail account as well as your secondary Gmail account.

Note: There is one limitation to this approach. When you send email from Hotmail as if it were from Gmail, Hotmail will note in the From information that it was sent from your Hotmail account on the behalf of your Gmail account. This may not be how you want that to read, but to my knowledge there is no way to suppress that note.

Collecting Hotmail-based email from Gmail

In this scenario, Gmail will be the main email account and Hotmail is the secondary account. You will use Gmail to collect email that was originally delivered to Hotmail.

In Gmail, navigate to Options | Mail Settings | Accounts and Import. In the section titled Check mail using POP3, click the button "Add POP3 email account." Gmail will display a short, multi-page wizard in a pop-up window. In the first stage of this wizard, enter the email address that you wish to collect mail from (your Hotmail account).

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Then, click the Next Step button.

The next page looks complex, but it's pretty straightforward. First, enter is the password for your Hotmail account. Then, examine the various options on this page, which are denoted with check boxes. You'll need to decide whether to leave collected email in the inbox of the secondary (Hotmail) account ("Leave a copy of retrieved message on the server"), whether to use a secure (SSL) connection, whether to label incoming messages (using Gmail's unique Label system) and whether to archive incoming messages. That last option refers to archiving on Gmail, not on Hotmail: If you select this, all of your incoming mail from Hotmail will skip the inbox so this is most likely not what you're looking for.

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(Hotmail has an interesting option that will prevent Gmail and other services and email clients from deleting Hotmail on the server even if those services and/or clients are configured to do so. To find this, navigate to Options | More Options | and then POP and deleting downloaded messages from within the Hotmail web interface.)

Click Add Account when you're done. Gmail will use the credentials you've provided to attempt and add your Hotmail account. When it succeeds, it will present a message to that effect and ask you whether you'd like to send mail from the Hotmail account from within Gmail. Click Yes or No to configure this option.

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Click Next Step again. In the next phase of the wizard, you can change how your name appears when you send mail from the Hotmail account, while using Gmail. (You can even provide a different "reply to" address, which is a curious option).

Click Next Step again. In the next page, you can optionally configure which Send Mail (SMTP) server to use for outgoing mail. There are two choices, through Gmail and through Hotmail. You want to choose the second option and send mail through Hotmail's SMTP server. Here's why: If you choose the Gmail options, all of the mail you send from Hotmail (through Gmail) will be sent with a From address like "From: [Hotmail account] on behalf of [Gmail account]." But if you use Hotmail's SMTP server, it will just be sent normally, with the correct (Hotmail) From address.

Click Next Step again. In this penultimate page of the wizard, Gmail notes that it must send a verification email to your Hotmail account to ensure that you really are the owner of that account and thus can authorize Gmail to operate on its behalf.

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Click Send Verification. Gmail will send a verification email and then provide an entry form where you can enter the verification code that was sent in that email.

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In Gmail, you will have received (or soon will) an email message from Gmail Team titled Gmail Confirmation - Send Mail as [account name]‏. This email includes the needed verification code and a hyperlink which you can click if you previously closed the Gmail wizard.

Copy the verification code to the clipboard and then return to the Gmail wizard, paste it into the waiting field, and then click the Verify button.

Gmail will return you to the Accounts and Import section of Gmail Settings. As you can see in this screenshot, two things have changed.

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In the Check mail using POP3 section, you can see that your Hotmail account has been configured for mail collection. And you can now edit the collection configuration or delete the account.

In the Send mail as section, your Hotmail account has been added a secondary account. If you want to, you can actually make your Hotmail account the default account for all new mail. And you can configure how replies work when you receive mail from the secondary (Hotmail) account; by default, you always reply from the same address as the message was sent to, so replies to messages sent to your Hotmail account will appear to come from Hotmail. But if you'd rather reply to all messages, regardless of origin, from the default account, you can do that as well.

Looking ahead

Email collection is the approach I prefer for cloud-based email aggregation, but in certain circumstance and with certain account types, the email forwarding method may be preferable. So I'll look at that method next. Stay tuned.