Chapter 2: Sending and Receiving Emails

Email has replaced the regular delivery of mail for many businesses and personal communications. No longer do we need stamps, paper, markers, or the time to run to the post office (although some do still utilize these services from time to time). On the whole, most of our communications can be done through email. There are all kinds of guidelines that you can follow to compose the finest emails. As you are composing your emails, there are three basic questions you want to be sure to answer with each of your emails:

1. Is your message understandable?
2. Is the intended message stated clearly?
3. Is the flow of the email easy to follow?

With some simple planning and being aware that the reader must decode the meaning of the communications (because of the lack of nonverbal communication such as facial expressions and body language), you should focus attention on the way you are composing your emails. Using the suggestions presented in this chapter will help to ensure that not only are your intentions written in your emails communicated effectively but you’re also composing your emails productively.

In this chapter, we’re going to cover the following topics:

• AutoComplete
• Email signatures (HTML)
• Attachments
• Recalling a message
• Voting buttons
• Replies – replying to other emails
• Working offline

For many of the emails that you send, this could be your first point of communication with the receiver. Following these techniques will help ensure that you are perceived correctly.

Sending and receiving email

When you open Outlook, the navigation pane will indicate that the Mail view is shown. The Mail view with the inbox displayed is the default view that will help you manage and navigate your email messages, unless you have customized your screen for another view to show (which will be covered in Chapter 16, Managing Your Day System).

To write and/or send an email, the Compose window will be used. Access this window by clicking Home | New Email. In this window, you will find the To and Cc fields. The Bcc field can be accessed by clicking on the To or Cc button, and in the Select Names dialog box, enter the email ID of the recipient in the Bcc field. If you do not enter a recipient in the Bcc field, it will not show in the Compose email window. You can also turn on this Bcc field by clicking Options | BCC.

Note

If the email address is underlined, that indicates that it is a valid email address. If no underline appears, then double-check the email address, as you will most likely get a delivery error message when you press Send. If you are sending to a lot of recipients, I suggest that you click on the Check Names button on the ribbon to have the email addresses all verified before sending.

AutoComplete

AutoComplete is word completion feature in Outlook. You may also see this written as the AutoComplete list, and the nickname cache is another name that it is referred to. The AutoComplete list is automatically populated with these names when you send email messages from Outlook and contains the email or SMTP addresses, legacy ExchangeDN entries, and the actual display names for email addresses to previous email recipients. When you begin typing into the To, Cc, or Bcc field in Outlook, suggestions will appear based on the text that you have entered. These suggestions come from this AutoComplete list, which is continually being updated once created:

Figure 2.1 – AutoComplete activated for the To recipient

After you reach the limit for entries saved in the AutoComplete list, Outlook uses an internal algorithm to identify names to eliminate them from the list. This is built on usage weighting. Because Outlook limits the number of entries you can save, you may discover names surprisingly removed.

The limits that are stored in the AutoComplete list are 1,000 entries for Outlook 2003, 2010, 2013, 2016, 2019, and 2021. The limit for Outlook 2007 is 2,000 entries.

Removing AutoComplete list entries one by one

Removing names from the AutoComplete list is the safest way to remove an entry so that a name will not appear on this list when you begin typing in the letters of the name. Keep in mind that once you remove a name from this list, it will be added back to the list once a new email is created again. The steps to remove an entry are as follows:

1. Open a new email message.
2. Enter a few characters of the AutoComplete item you want to eliminate from the list. When the name appears in the list of suggested items, hover the mouse pointer over the desired entry to delete. Once it becomes highlighted, wait for the X icon to appear next to the highlighted suggestion and click X to remove, or press the Del or Delete key on the keyboard.

Figure 2.2 – Deleting the AutoComplete list entry

Selecting X will prevent the named entry from appearing in the AutoComplete list again but won’t remove it from your account. Because of this, the entry will still appear in other areas of Outlook, such as in search boxes.

Using contact addresses for the AutoComplete list

Instead of waiting for the AutoComplete list to populate and save all your email names to cache, you can also populate this list with your contact addresses in Outlook by making a new message. Address the message to all contacts. Make sure that you don’t send the email messages. The following shows the steps to do this:

1. On the Send/Receive tab, click on the Work Offline button so that the email does not actually get sent to your contacts. Work Offline will be discussed later in this chapter.
2. Create a new message using Home | New Email.
3. Click the To button.
4. Select the contact list from the address book where you want to add your contacts. Your options will be as follows:
   • A contacts folder
   • A global address book
   • A contacts folder that resides within a public folder
5. Select the first contact, and using your keyboard or mouse, scroll to view the last contact. Press and hold the Shift button on the keyboard while clicking on the last contact to select all contacts, and click OK. The dialog box will close.
6. Ensure that you placed Outlook in offline mode using the Send/Receive tab so that the email does not actually get sent to all your contacts. Now, in offline mode, send the email, and then delete the message from your outbox in the navigation bar on the left of the mail view. Once deleted, you can revert to online mode.
7. Test this by addressing a new message; note that the AutoComplete attribute will appear with your contacts’ email addresses.

Enabling or disabling the AutoComplete list

The default setting for AutoComplete is turned on or enabled. Here are the steps to locate this setting:

1. Select File | Options.
2. Select the Mail tab from the menu on the left.
3. Scroll down to the Send messages section.
4. Ensure that the Use Auto-Complete List to suggest names when typing in the To, Cc, and Bcc lines box is checked. Uncheck this box to turn off the AutoComplete list feature.

By deselecting this box, the AutoComplete drop-down box will not appear when you start typing the first few letters of the recipient’s email address.

Figure 2.3 – The Outlook options for AutoComplete

Note

For Outlook 2003 and 2007, you will find this setting in the Advanced Email Options tab. Check or uncheck the Suggest names while completing To, Cc, and Bcc fields option.

Figure 2.4 – The AutoComplete option for Outlook 2003 and 2007

Clearing all entries from the AutoComplete list

You may decide that there are too many names to delete from your AutoComplete list.

To clear or empty an AutoComplete list, do the following:

1. Go to File | Options to open the options dialog box.
2. Click Mail in the left navigation menu, and then click the Empty Auto-Complete List button in the Send messages section.

Figure 2.5 – Emptying the AutoComplete list

A dialog box will appear and ask for your confirmation to empty the AutoComplete list. Click the Yes button, and then click the OK button in the Outlook Options dialog box.

3. Now, the AutoComplete cache will be cleared from Outlook.

   Note

   Once you start creating new emails, the cache will display again.

HTML email signatures

Outlook signatures appear at the bottom of your email and usually contain your contact information for the recipient to easily get a hold of you. You can enter more information in this box besides text. Some types of data you can include are as follows:

• Text
• Images
• Electronic business card
• Logo
• Handwritten signature

Outlook signatures will be automatically inserted into every outgoing message. Create them if you wish to add them to your emails as needed.

A good Outlook signature is typically an HTML signature. Without HTML, an image will usually get distorted on different devices, and with simple text, it will look unprofessional. An HTML signature makes your email look professional and makes a great impression on your recipients, which will encourage them to get in contact with you.

Before you can insert the HTML signature in Outlook, you first must create the signature. There are tools online to help you do this or a graphic designer can do it for you. Once they give you the file, you will need to save this to your computer in a location from which you will be able to easily access it.

The steps to insert an HTML signature into Outlook are as follows:

1. Have your created HTML signature saved to your computer in an easily accessible location.
2. In Outlook, select File | Options | Mail and click on Signatures….
3. Click on New to add a signature, give a name, and click OK. Select the email account on the right of the box. Close the signature dialog box and close Outlook.

Figure 2.6 – Creating a new signature

4. Hold the Ctrl key on the keyboard and click on the Signatures button. This will open the File Explorer with the Signatures folder open, which is where Outlook saves the signature files on the computer. Select the .htm file that was created in the previous step and delete the file.

Figure 2.7 – File Explorer | Signatures

5. Now, select the HTML file that you saved on the computer in step 1 and copy the file. Then, go back to the Outlook signature file location and click Paste. Right-click on the file to rename the file as whatever you named it in step 3. Change the file extension to .htm instead of .html. Press Enter and confirm the file extension change.

Figure 2.8 – Changing the extension to .htm

6. Switch back to Outlook and click on Signatures again. You will see that the new signature has been created; however, you may not be able to view the picture.
7. To test, create a new message, and the HTML signature should be inserted within the body of the message.

This method is different from copying and pasting your HTML signature into Outlook’s signature settings. It involves opening the .htm file that Outlook generates and replacing it, which ensures that the correct HTML and image paths are being sent. This method ensures that the images are clear. If you install your email signature by copy and pasting, Outlook edits your code, replacing it with its own Microsoft Word-rendered code, and compresses your images, which will reduce their quality.

Attachments

Attaching files, pictures, contacts, emails, and many other items to your Outlook messages is a very easy process. To attach a file, simply click on Insert | Attach File on the ribbon. Next, choose the file from one of these locations, prompted by the drop-down menu:

• Recent Items – The 12 most recent files worked on will be displayed.
• Browse This PC… – Opens File Explorer to navigate to the file.
• Browse Web Locations – Including OneDrive, SharePoint sites, and other locations. Select one of the locations and then select your attachment.

If you select a file on your computer, a copy of the file will be attached to the email; however, if you choose a file in the cloud, you can follow the steps that follow to add cloud file attachments in Outlook.

Cloud file attachments in Outlook

The attachment options allow you to control how a file that you attach from OneDrive or SharePoint is attached to your email. The default settings ask you how you want to attach a file to an email every time. To change this default, select File | Options | General and select your preference under the Attachment options section. Your options are as follows:

1. Ask me how I want to attach them every time
2. Always share them as links
3. Always attach them as copies

   Note

   If you do not have the attachment options displayed on the General tab, you will need to install the KB4011240 update for Outlook 2016, dated November 7, 2017.

Multiple attachments

If you are sending multiple attachments in one email, you can download them to your computer in one step instead of opening each attachment and saving it to your computer. Click on the middle of the attachment, click the drop-down arrow next to the attachment, and click on Save All Attachments…. Then, you will be prompted to save all the files to a selected location on your computer.

Figure 2.9 – Save All Attachments…

Changing the file association for an email attachment

Many file attachments can be opened by more than one type of program on your computer. One example would be opening a photo with the Photos program or with Paint. The following steps can be used after you have saved an attachment.

To open the default program with another type of file instead of the file type of the sent attachment, follow these steps:

1. Locate the file to open in the File Explorer on your computer.
2. Right-click on the file and select Open with….
3. Select the application that you want to associate the file with or select the store to find a suitable application.

Figure 2.10 – File association

You will need to change the program to open a file with if you do not have the software on your computer. In most cases, you will have an adequate program with which you can view the attachment. However, if that is not possible, you may have to ask the sender to convert the file to a compatible format for you to view.

Voting buttons

By using voting buttons in email messages, you can poll all your recipients and ask questions with a limited set of answers, which is especially useful for large groups. The recipients can use the voting buttons to respond to your email, and by doing this, your results will automatically calculate for you. You can also export the responses to an Excel worksheet.

Note

A Microsoft Exchange Server account is required to use voting buttons.

Inserting voting buttons

1. Click Create, Reply to, or Forward from an email you received.
2. Choose Options | Use voting buttons.
3. Select one of the following:
   • Approve; Reject – Used for receiving authorization for an action.
   • Yes; No – Used for a quick poll with yes or no.
   • Yes; No;Maybe – Used to offer alternative responses to yes or no.
   • Custom – If you choose this option, you will need to use the Voting and Tracking options settings in the Properties box, and check the Use voting buttons checkbox, as shown in the following screenshot. Delete the default text and replace it with your own, using semicolons between each entry.

Figure 2.11 – Voting buttons

Occasionally, you may have a recipient of your email not realize that there are voting buttons in the email to click on to place a vote. I would suggest including a reference them in the subject to make them aware of the voting buttons, which may help you receive responses promptly and correctly.

Tracking and printing results

After receiving results from the recipients of a sent email, it is efficient to use the Excel tracking feature to track and print them:

1. In Outlook’s Sent Items folder, locate and open the email message you sent.
2. Click the Message tab | Tracking. The Tracking button will not be seen until at least one person has voted in the poll from this sent email.
3. The results will appear in the Results window with a blue box that shows the tally for the responses. You can then print the window using File | Print, selecting a printer, and selecting Print.
4. Send the results to an Excel workbook by clicking Message | Tracking. Click and hold Ctrl, and then click and drag to select the names and responses. Copy the selection, open a blank Excel workbook, and paste the data into Excel at your desired location. You will then need to adjust the column widths and so on in the worksheet to be able to see all the data.

Recalling a sent message

I bet that we have all sent an email in error. This can easily open the potential for some real damage, although it is usually just plain embarrassing. Outlook has tools built-in for these scenarios, and I suggest you practice this tip before suddenly needing it. This is a good technique to pull in a co-worker and practice sending and recalling messages between one another so that if or when the time comes to act, you will be ready to act fast and not have to figure it all out. Once you realize that you sent an email in error, these are the steps to quickly recall that message:

1. Select the Sent Items folder.
2. Double-click on or select the message so that it opens in another window.
3. Select File | Info.
4. Select Message Resend and Recall | Recall This Message.
5. Select Delete unread copies and replace with a new message to replace the sent message with a new message. When you click Send, the original email message will be deleted and replaced with the newly edited one if the email has not been read.
6. Select the Tell me if recall succeeds or fails for each recipient checkbox. Then, select OK to close the dialog box.

   Note

   If your office account is an IMAP or POP account, in Chapter 3, Managing Email Accounts, a recall won’t work. Also, the recipients must be on Exchange or Microsoft 365 and reside within the same organization to be able to recall a sent message.

Handling replies

When a person replies to your emails, that reply by default will go back to the originator of the email message. In Outlook 2016 and later, you have the option to redirect replies to another email address than yours. This is very useful if you are going on vacation and want messages replied to someone other than yourself for that time period.

To have replies directed to someone else, click the Options tab | Direct Replies To.

Figure 2.12 – Direct Replies To

Within the Properties dialog box, Delivery options will have a checkbox by Have replies sent to. If the box is not checked, you need to check it.

Figure 2.13 – Properties for Delivery options

In the box to the right of this, enter the name of the email ID that you want the replies sent to from now on. You need to remember to change this as needed. If you prefer, or do not know the email address, you can click on the Select Names… button and then choose a name from the selections.

Note

The recipient won’t know that you have chosen to redirect replies to another address until they click the Reply button and see a different email address shown in the To field.

Working offline

The working online/offline feature was added to Outlook in the 2010 version and has remained in all later versions. The purpose of this button is to allow users to be able to access their work on Outlook without internet connectivity. In offline mode, you are still able to access loaded emails and compose new emails; however, you can’t send or receive new emails. If you send in offline mode, your emails will be scheduled to be sent as soon as an internet connection is available and when you have regained online features.

Is Outlook working?

There are two ways to identify whether Outlook is working or connected to the internet:

The display settings on the status bar will indicate that you are connected to the Exchange server on the status bar.

Figure 2.14 – Outlook is connected to the internet

If the internet is down, you will see an indication that you are working in offline mode.

Figure 2.15 – Outlook is not connected to the internet

Click the Send/Receive tab, and at the far right of the ribbon is a Work Offline button. If the button is not grayed out, it indicates that you are connected to the internet, and the status bar will show that you are connected.

Figure 2.16 – Outlook is connected to the internet

If this button is grayed out, then the internet is not connected, and you will see the Work Offline text on the status bar.

Figure 2.17 – Outlook is not connected to the internet

When Outlook shows that it is disconnected

If your Outlook is indicating that your status is working offline, then it most likely is an issue with your network connectivity. Start the troubleshooting steps by first clicking on the Work Online button. This may be the only problem, but if not, you need to begin checking with your internet provider or IT staff to determine whether they have a problem. If not, here are some possible connectivity issues to consider:

• Mail server issues.
• Incorrect account settings.
• An outdated operating system.
• The Outlook Exchange server is down – you can log on to the web account to check.
• Check for any Outlook updates that are needed to be installed.

There are several possible solutions to get you back online. You can connect with Microsoft or your email provider, who will quickly get you up and running. If you do have internet connectivity, you can reach out to Microsoft at https://support.microsoft.com/.

Summary

Like it or not, email is here to stay, and it is important to have an efficient workplace. The topics in this chapter will help you to communicate and distribute your content in a professional matter to your clients, coworkers, management, or anybody that you have a need to communicate with. You may feel that your email is overwhelming. It’s time to take back control by utilizing the AutoCorrect feature, creating email signatures, and having replies sent to another person, which were all established to save you time.

In the next chapter, we will discuss managing your email accounts and what is necessary for setting up and maintaining those accounts. We will discuss selecting an email provider, selecting domain names, and using multiple email accounts.

Questions

1. How can you have an attachment appear in the body of an email?
2. Why might your Outlook suddenly disconnect?
3. Can you swap one signature for another in an Outlook email message?
4. What is the Outlook web app?
5. What is the maximum size limit for an attachment in Outlook?

Answers

1. Create a new email message (you can also reply to or forward an email) and select Insert and the drop-down arrow next to Link. Choose a file from the most recently used items, or at the bottom of this list, choose Insert Link… and the file to attach, and click OK. To attach more than one file, hold Ctrl while selecting multiple files. The link for the file or picture, if selected, will appear in the message of your email.
2. This is most likely due to a temporary hiccup in the connectivity to the network/Virtual Private Network (VPN). Check to see whether you are still online by looking at the status bar, which will display Connected to: Microsoft Exchange or Working offline.

Figure 2.18 – Working offline

Outlook will automatically try to reconnect to the server, but if that does not work, you can click on the Send / Receive tab | Work Offline button. If this button is grayed out, you are offline, and no shading indicates that you are working online.

3. In a new email message window, select the Message tab | Signature drop-down arrow. Any previously created signatures will appear in this selection. Select the signature that you want to swap the current signature for. You can also select the signature…. option to create a new signature from this menu button.
4. Outlook Web App (OWA) allows you to access your email account from a web browser. Outlook on the web does not include all the features found in the Outlook desktop version. It is a slimmed-down version that allows you to access your email while away. You can access the web browser at outlook.office.com.
5. Microsoft has a 20 MB limit on attachments that you can send through email. It does not matter whether this is a single file or several files attached to one email. The total size of all attachments cannot exceed 10 MB to 35 MB, depending on your plan. If you need to attach a file that is larger than what your plan allows, you should consider putting the file in a shared location and emailing a link to that location instead. See Further reading for the Exchange Online limits.

Further reading

• Exchange Online limits:

https://docs.microsoft.com/en-us/office365/servicedescriptions/exchange-online-service-description/exchange-online-limits?redirectedfrom=MSDN#MessageLimits