The easiest way to generate a PDF is to simply select an Outlook item, either from the Explorer window or by opening the Outlook item in its inspector window, and clicking the PDF ‘Export As‘ button.

If you want more options on the export, click the drop down menu to export the email and attachments individually as PDF or combine all of them to a single one PDF file.

In Outlook 2016, these menu items are available under the context menu (i.e., popup menu you get when you right-click the selected items)

Context menu when a single item is selected:

And you can then export the selected Outlook item to a PDF or other support document format. In the ‘Save As’ dialog, the file name of the document to be generated is pre-filled with metadata information of the selected Outlook item. For example, below in the screenshot, the file name is in the format Subject + Underscore (_) + Received Time + Underscore (_) + Sender Name. This way you don’t even need to input and key in the name of the document.

You can of course customize what metadata information is used from the Outlook item to name the generated document from Outlook > Email to PDF toolbar/ribbon > Settings. You can customize the default naming scheme for different type of Outlook items such as mails, appointments or tasks separately.

When you combine email and attachments to a single one PDF document, the add-in will use the default windows file sorting algorithm (i.e., alphabetically) while merging your attachments to the one PDF file. If you do want to alter or re-order the sequence of the attachments, you can use the advanced merging mode as shown below:

And from the customize files order window, you can change or sort the order or sequence of the files in the way you want them to appear in the merged PDF file. Use the up and down arrow buttons to change the sequence or, you can also drag and drop files using your mouse in the order you want. If you have some unwanted attachments that you don’t want in the PDF document, you can simply uncheck them for exclusion. You can further overwrite the default watermark, security, page layout or orientation for this particular action only.

NOTE: If the attachment is a zip or MSG or EML file, this advanced mode will scan through the composite file and show you the intrinsic file components and these files can be too re-arranged in the sequence or excluded to give you finer control on the composition of the final PDF document. The add-in can will recursively scan upto 3 levels on a composite attachment file (such as zip, MSG or EML file).

Click here to see all the attachment file types that are supported for direct conversion to PDF

When you select multiple emails, the drop down options under the ‘Export As‘ menu will change to reflect the varied way of batch processing the items and export to a document format. One of these options is to generate individual PDF or document format from each of the selected Outlook item in batch.

This ‘Batch Export’ dialog enables you to specify the destination folder where all the document files would be saved. You also have the option to choose what file title the generated documents would take – either a defined generic name or use metadata information extracted from the Outlook item, such as Subject, Sendername, ReceivedTime etc.

In Outlook Explorer window, select multiple emails and from the drop down options under the ‘Export As‘ menu, and you will see the sub-menus change to reflect the varied way of batch converting the emails to document formats. One of these options is to generate a single PDF file from multiple emails and their attachments.

You will be prompted to specify a filename and the folder location to save the document.

Furthermore, when emails and attachments are merged to generate a single PDF file, the add-in automatically adds bookmarks, page number and even custom footer information such as your company name in the PDF structure tree for easy navigation to the individual email and attachment in the PDF.

Email to PDF add-in supports appending emails and their attachments to an existing PDF file. The emails and their attachments will be converted to PDF format and would be appended at the start or end of the specified existing PDF file (depending on the settings).

Before sending emails to recipients, Email to PDF add-in provides you an option to convert any attachments (that you might have added) to PDF. You can choose to convert and embed the PDF versions of the attachments, in either separate PDF file for each attachment, or a single merged all-in-one PDF file containing all the attachments. Whether the attachments are Word, Excel, PowerPoint, Web, images, multi-page TIFF or simply plain text documents, the add-in would automatically convert to PDF.

Here is a demonstration of this feature. Below is a reply that is made to an existing email. And 2 attachments of different types (eg. Word and Excel documents) are added as attachments.

Before pressing the ‘Send’ button, click the ‘Embed PDF version of attachments‘ option available under the ‘Email to PDF’ ribbon toolbar (just adjacent to the ribbon group that contains the ‘Attach file’ Outlook button).

Pressing one of the PDF embed option would result in converting the attachments to their PDF equivalents and the PDF files would be added to the email. For instance, below shows when the embed output to individual PDF is chosen.

And below show a single PDF being added, when the embed option for merging all attachments to a single PDF file is chosen

You can then choose to remove the non-PDF attachments that were added already before you press the ‘Send’ button.

If you have an iPad, iPhone or other tablet devices, you would have probably experience the inability to view various attachment file formats from within your email. PDF format support, is however built-in natively in most of these devices and you can easily preview the PDF attachment within the email. Keeping this limitation in mind, Email to PDF add-in now supports embedding the PDF version of the attachments back to the email, so that you can easily preview all the non-PDF attachments in your hand-held device. You can choose to merge all attachments to a single PDF, or to separate PDF files, and embed to the original email.

Email before embedding the PDF version of the attachments:

Email after embedding a single one PDF version, combined with all the attachments:

Email after embedding separate PDF version of each attachment:

A major feature of Email to PDF add-in is the real-time monitoring of any number of Outlook folders. This will automatically process incoming mails or newly added appointment and task items and generate PDF or other documents based on the user chosen format, without any intervention from the user. This automatic conversion of Outlook items to PDF or XPS documents requires no input and intervention from the user. Now, you can easily maintain a parallel copy or backup of your current Outlook items.

Automatic export works by allowing Email to PDF add-in to monitor user specified Outlook folders, such that, when new emails are received or new appointments or tasks are added, the add-in automatically processes those items in real time and generate document files as per the user pre-settings for that particular Outlook folder or mailbox.

To add a new Outlook folder, for automatic export

When you press the ‘Select Folder…’ button, you will be prompted to choose an Outlook folder, that would be monitored by the add-in for automatic export. You can select a Mail/Post items folder ( ), or an appointment folder ( ), or a task folder ( ). This folder can be a public folder or a shared mailbox folder also.

Adding watermark is a simple way to secure your PDF content. A watermark easily lets viewers identify the status of your PDF content, for instance, as a visual warning to designate your document as confidential or for internal use only. More importantly, watermarking each page of your PDF helps protect your intellectual property from being passed off as someone else’s work when it is shared with others. Adding a watermark of your company logo or brand on publication material not only adds a professional touch but also helps to identify ownership without completely locking the PDF down.
To add a watermark image or text annotation to your PDF files, you will need to create a profile under Outlook > Email to PDF toolbar > Output Settings > Watermark tab.

Click the ‘New’ button to create a watermark profile. You’ll get the following dialog box where you can choose the type, position of your watermark. You have two options on how to create a watermark:

1) Text as watermark

Click on the ‘Text as watermark‘ radio option. Type in your text (such as your company name or brand etc.). Customize the Font, Size, and Color of your text watermark. You can adjust the opacity of the watermark to allow text from behind to show through. You can also adjust the angle and rotation at which you want the watermark.

And this how the converted PDF file appears like when viewed in PDF viewer – with the custom text (e.g., company name embossed in each of the page)

2) Image as watermark

Click on the ‘Image as watermark’ radio option. To insert an existing image as a watermark, click on the Image button located at the extreme right corner and browse the open dialog box and select your image from your computer.

And this is what the converted PDF file looks like (in PDF reader software) – with the image embedded in the middle of each page of the PDF.

NOTE: It is possible to define multiple watermark profiles. However, you will have to choose only one default profile that would be applied to the PDF generated by the add-in in Outlook. And you do that from the drop-down field.

Or, even simpler, you can choose or switch to the desired watermark profile from the PDF toolbar in your Outlook.

And doing this will apply the chosen watermark to PDF outputs by default. If you don’t want to watermark your PDF files from Outlook, just don’t choose any default profile i.e., specify default profile as empty.

A PDF file on its own is not as secure as you may think. Despite the versatility of PDF (as a universal file format) that preserves the look and feel of your original document regardless of platform or device, without security settings on your PDF publication, there is no way to prevent malicious users from tampering the file and taking credit for your content.

With Email to PDF add-in, you can lock down the PDF files generated by setting password encryption and limited file permissions. To enable this, you will first have to define a security profile under Outlook > Email to PDF toolbar > Output Settings > Security tab.

Click the ‘New’ button to create a new profile. The security panel option shows up and has two sections – Document Open and Permissions.

Check the option ‘Require a password to open the document‘ under Document Open section (1) to set a password that will be required by your intended recipients for opening and viewing your PDF content. And type the password in the box. This is the simplest way to filter out your intended recipients from malicious users. With a password, your PDF content is locked and act as a first security layer to secure your information at the most basic level.

Check the option ‘Restrict Editing and printing of PDF’ under Permissions section (2) to add another level of security to your PDF content should your file be accidentally accessed. While people may be able to view it, ensure that viewing is all they can do with it. For instance, you can restrict activities from printing content to copying text. You can also set a master password so that in case you want your team members to perform unrestricted activities on the PDF material, they can do so by entering this master password.

Once done, save the profile. It is possible to define multiple security profiles. However, you will have to choose only one default profile that would be applied to the PDF generated by the add-in in Outlook. And you do that from the drop-down field.

Or, even simpler, you can choose or switch to the desired security profile quickly from the PDF toolbar in your Outlook.

And doing this will apply the chosen security to PDF outputs by default. If you don’t want this, specify default profile as empty.

Checking the PDF’s Properties > Security dialog in any PDF viewer, users can see what permissions are given to the file, if any.