Building your mailing list from contacts in your Inbox or Sent Items folders

How to build your mailing list by automatically discovering contacts you have previously communicated with, from within your Inbox and Sent Items folders.

Most people have contacts which they would like to email again or reach out to, but perhaps you had not taken the time to add them to your Outlook contacts or distribution lists.  Some of these people may have emailed you an inquiry at one time, but had not responded to your reply at the time, and became buried under a pile of new email.

PoliteMail provides a neat way to discover all these contacts, by scanning the mail items in your Outlook inbox, sent items folder, archieve folders, or any Outlook mail folder.  You will be amazed at just how many contacts PoliteMail will find, and may have one of those “Oh yeah, that person!” moments.

Of course, one of the side effects is the collection of a bunch of unwanted names and addresses as well – any spam sender that is in your inbox will be included, as would your mothers email if you one from her.  So after the import, you will want to go through the list, and delete the unwanted contacts, but should be pleasantly surprised at just how many good contacts you will come up with.

Start from the PoliteMail menu, and choose Manage Lists, then use Actions > Import from Outlook.  Select the Outlook folder you want to import (e.g. your Inbox, Sent Items, or whichever – but just one at a time).  Now let the process run – it may take a while if you have a large Outlook folder.

Create Mailing List from Outlook

PoliteMail will generate a CSV file of the discovered contacts, and being the import process. Give your list a name, then go to the next step. Usually the only fields will be Email Address and Display Name (select display name from the pull-down list, in the align data fields dialog).
Now complete the import process and PoliteMail will give you a summary of the contacts found.

To remove the unwanted contacts from the list, use PoliteMail > Manage Lists, double-click the mailing list you just made. Now check any contact you do not want, and use the X – Delete Contact(s) option to remove them.

At this point, you should have a nice list of contacts that you have previously had email communications with before!

PoliteMail not loading error: add-in is not in trusted source list

If, after installing the PoliteMail for Outlook add-in, it doesn’t load but instead Outlook gives you and error dialog that says “Load Behavior not loaded Certificate of signed and load at startup com add-in is not trusted source list” then you most likely need to run Windows update or Office update.

The PoliteMail COM add-in for Outlook is a signed with an SSL security certificate, which must be trusted by the Windows OS and Office system. If you are running an older Windows system, such as Windows XP, and you are not up-to-date with patches and service packs, then the list of root certificates may not included the newer security cerficiate used by PoliteMail to sign the add-in.

If you run both Windows Update (and include the root certificates update) and Office Update, this should resolve the issue.

Why does my email have images as file attachments?

Is your Outlook email being received with images as file attachments, including some images that should not be in the email, or duplicate images?

Unfortunately Outlook handles images pasted (or inserted via Outlook’s Insert Picture command) into the email as file attachments. This doesn’t show up when sending to other Outlook users, but does show as attachments when sending to web mail clients (such as Yahoo, Hotmail or Gmail) or smart phones.

When you replace or delete images, Outlook keeps the old images temporarily embedded in the email. However, when you save this file as a template, all those image attachments get included, which is why you may see old image versions as file attachments. If you continue to use the previous email from your Sent items folder or PoliteMail template as your starting point, those file attachments will still be included.

To resolve the image attachment issue. Here’s what you do:

  1. Open the email, select-all (Ctrl-A) and copy (Ctrl-C).
  2. Start a new email message, and paste (Ctrl-V).
    This action will clear out those unused image attachments.
  3. Now select the image, and use the PoliteMail > Add Graphic Image command, find the image on your desktop, and load it.
    This action will replace the embedded image with an image referenced from the PoliteMail server, with the added benefit of making your email size smaller and faster.
  4. Add a subject line, and include the word [TEMPLATE] at the beginning of the subject line.
  5. Now use PoliteMail > Save As Template. This is put a copy of the clean message in your template library. Use this template to create a new version of the next email, instead of the sent item.
  6. Now remove the [TEMPLATE] from the subject line.
  7. Test the result using PoliteMail > Preview/Test Send and sending to your Yahoo, Hotmail or Gmail account (see, no attachments!).
  8. Now go ahead and send to your list (with 1to1 with Tracking selected).

Here is some additional information from our Knowledge Base:

Why sending one big image as your email isn’t a good idea

Adding Graphics and Pictures to an Image

How to keep Outlook from automatically embedding images

Step 3: Track Results with Email Metrics

Track Results with PoliteMail Email Metrics – Know Who Opens & Clicks!

After sending your tracked PoliteMail messages, you will be able to see results within the Recent Interactions panel and the Email Metrics reports.

If you have the PoliteMail panel open next to your inbox, you can monitor this interactivity in real-time. This panel automatically updates about every 3 minutes, with the most recent interactions at the top in yellow, which fade to white and then gray as they get older. Use the Recent Interactions > Refresh option to get the latest information.  Also see Understanding Interactions

Track Outlook Email Opens and Clicks in Real-Time

To see total results, use PoliteMail > Track Results to view the Email Metrics Reports for your send(s).

  1. Use PoliteMail > Track Results
  2. In the Messages tab, double-click the message to run the email metrics report
  3. Drill down into any metric, by clicking on the underlined numbers
  4. Export your report using the Excel or Word links at the top right of the report

Step 2: Send a tracked message

Sending PoliteMail Messages

You send PoliteMail just like your send your regular Outlook email. The only thing you have to do differently when you want to send tracked PoliteMail, is to select the 1to1 with Tracking option at the top of Outlook’s new message window.

  1. Start a New Outlook message
  2. Put your lists or individual addresses into the To: field
  3. Select 1to1 with Tracking
  4. Click Send

When your PoliteMail Server setting is set to send via the Outbox (the default) you should see PoliteMail process all the individual recipients, and put the total messages into your Outbox.

This works best for list and group sends of Send email via PoliteMail Server option. With this option, the email will be delivered via a PoliteMail Server, or for corporate accounts can be figured to deliver to your Exchange Server (for internal communications).

Step 1: Register your connection with the PoliteMail Server

Register a Connection with the PoliteMail ServerAfter installing the PoliteMail for Outlook add-in software, the first step to getting the software running is to register your license and connect to the PoliteMail tracking server for your account.

The registration key and server name will be provided to you via email once your account is established.

Here’s how to get registered and connected:

  1. On the PoliteMail Connection Settings dialog, enter your email address. Use the address you set-up your PoliteMail account with. Please note this will not necessarily be your Send From address, as PoliteMail will always use your currently selected Outlook account as the From address.
  2. Now copy the registration key from your account email, and paste it into the Registration Key field
  3. Now click the PoliteMail Server tab, and ensure your PoliteMail Server entry corresponds to the server provided along with your credentials. This is the domain for the PoliteMail tracking server your account is set-up on (this is notyour SMTP or Exchange Server address).For corporate cloud accounts, you will have a unqiue server name such as “”. For licensed servers, your IT staff will generate the name, and provide it to you, typically in a form such as Please note, the server name must be a fully qualified domain name.
  4. Use SSl is checked by default. SSL enables an encrypted (https) connection between your PoliteMail for Outlook software and the PoliteMail Server. Only in the case when you are running an internaly licensed PoliteMail Server, and your IT team has not installed an SSL certificate on the PoliteMail Server system, then to connect properly you will have to uncheck the use SSL selection.
  5. Now click OK, and your connection should be established.

If you receive an error message, “Your credentials or host name are incorrect…” please double-check the account email address, registration key, and PoliteMail Server settings. All three of these must be current and correct in order to register and connect to the PoliteMail Server.

The text or layout of PoliteMail pages and reports looks too small/condensed

If your PoliteMail pages and reports do not look right (see example below) then most likely the Text Size setting in Internet Explorer is set to small. You can fix this by setting it to medium (normal).

This is most likely seen if your are running Windows XP and Internet Explorer 8. If you had made that setting in IE8 but had upgraded to IE9, the setting would still apply but the menu option would not be visible by default.

Here’s how to fix it:

  1. Close Outlook
  2. Open Internet Explorer (IE)
  3. Use the View menu, select Text size, and select Medium

    If you don’t see the View menu or are running IE9, use the Tools menu, and select Menu bar. Now you should have a View menu option.

  4. Now restart Outlook
  5. The layout of the PoliteMail pages and reports should

How to add contacts/addresses/domains to your Outlook whitelist to ensure inbox delivery

If an email message you want ends up in your spam folder by mistake, you can prevent that from happening again by adding the senders email address or email domain to your Outlook whitelist.

In Outlook 2010, from the Home tab click Junk, the Junk E-mail Options…
In Outlook 2007, use the Actions menu, click the Junk option, then Junk E-mail Options…

In the Junk E-Mail Options dialog, cick the Safe Senders tab, the Add the addresses or domains you want. Then click OK.

An email address I typed into the To: field didn't get delivered

If you manually typed an address into the To: field, you sent tracked and the email was never delivered, then there are a couple of possible reasons.

  1. If you sent this email to yourself, see this article
  2. The “nicklist list” that is used for the auto-complete in the To: field has an error
    This could happen due to an address change, or an active directory group change on the Exchange Server, or a previous input error. Follow the process below to reset/rebuild your nickname list.

    The reason this occurs (but works when you send a regular Outlook email not tracked by PoliteMail, is because PoliteMail doesn’t have access to all the internal functions of Outlook, it requires an SMTP email address (an address in the form “”) in order to be able to send successfully. Outlook however, can use a network address or Exchange address to reference the updated email, and successfully deliver the email. If you double-click on the name in the To: field and get an Outlook error dialog that says something like “The entry could not be found, the address has moved” this is likely the problem – as PoliteMail would not have a handle to the updated SMTP address.

Use this Microsoft support article to fix it: How to reset your nickname/auto-complete list

Why didn't the email get delivered?

Sometimes email doesn’t make it to the inbox, and there are a variety of reasons for this.

  • Sending one big image
    This type of email message breaks the most common spam filter rule. For example, if you were to send an email which was just one big .jpg image (such as one you created in photoshop, with all the fonts, colors, etc. built into on big graphic), the majority of recipient would never receive it. Why? There is a rule common to most spam filters that says if an email is all image with very little or no text, then it is most likely spam, and should be blocked or routed to the spam folder.

    It’s always a good idea to create an email with both text and images – and you need to use more than just a few words of text.

  • Sending a “test” message
    Another example of breaking a common spam rule which may get the email blocked altogether or routed to the spam folder would be if you sent a tracked email with just a single word or two like “test” in the body of the message. Because tracked messages include a transparent tracking image, and the email contains very little text, spam blockers see it as a common form of spam.

    It’s always a good idea to send a test message that resembles what you will actually be sending – or at least include a couple sentences of text and perhaps a link.

  • Sending a message to yourself, via the PoliteMail Server
    In this scenario, even though the email is being sent from your email address, it is being sent from our mail server system, therefore (depending upon your email configuration and security/trust settings) your email server may know it didn’t send, and therefore will block the message delivery.

    This problem can be overcome by adding your politemail server name (e.g.,, or whatever server you are on – see PoliteMail > Connection Settings) to your trusted zones, or by adding the domain name to your Outlook whitelist.

    See also: How to add contacts/addresses/domains to your Outlook whitelist
    How to add to your trusted zones

  • Manually typing an address into the To: field, that doesn’t get delivered
    In this scenario, you colleague didn’t receive a tracked email, but can receive it when you send untracked. This is typically due to an error in Outlook’s “nickname list” that is used for the auto-complete when you are typing names into the To: field. This could happen due to an address change, or an active directory group change on the Exchange Server. Because PoliteMail doesn’t have access to all the internal functions of Outlook, it requires an SMTP email address (an address in the form “”) in order to be able to send successfully. Outlook however, can use a network address or Exchange address to reference the updated email, and successfully deliver the email. If you double-click on the name in the To: field and get an Outlook error dialog that says something like “The entry could not be found, the address has moved” this is likely the problem – as PoliteMail would not have a handle to the updated SMTP address.

    The solution for this is to reset your nickname/auto-complete list.
    Also see this article

  • Having your mailing IP address or domain blacklisted
    This is the lease common problem, but does occur if you are sending large volumes of unsolicited email, or even when sending moderate volume of unsolicited email to mostly free email accounts like yahoo, hotmail, gmail or aol. If you recieve a certain number of spam compliants in a short period of time, your email could become blacklisted. If this occurs as part of a send via the PoliteMail server, we would recieve notification, and you would be notified. Otherwise, you can check using a free service like mxtoolbox blacklist checker.