A few days ago, I worked on a case where I noticed that so many Outlook attachment files were not processed in an appropriate manner. The attachment files are named as olk14MsgAttach in Microsoft Outlook 2011 for Mac and olk15MsgAttach in Microsoft Outlook 2016 for Mac.

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Earlier, there was no MS Outlook for Mac, there was another email client i.e. Entourage. It provides ease while using the email application as it does not have any PST or OST file. It only uses a Main.db file to store all its mailbox data and users can also extract emails and attachments in the form of EMLX files.

Overview of OLK Files

While going to the Office Suite of Mac, Microsoft finally released Outlook for Mac in 2011. It didn’t create OST and PST to store its mailbox data. Instead, they created separate directories for storing emails, attachments, contacts and other mailbox items. Outlook for Mac uses .olk14folder file for storing email folders, .olk14contact file for storing contacts, .olk14search for storing saved searches, .olk14pref for saves software preferences, .olk14category file stores categories for tagging emails, calendar, contacts, etc. There is another file created in Outlook for Mac i.e. .olk14UID which is associated with Outlook only. Then, it uses .olk14signature file for saving saved signatures, .olk14msgsource for storing the content of email messages, .olk14schedule contains saved schedules. There is one another file which contains the recent email address i.e. .olk14recent file. The .olk14mailaccount file contains the login information of the email account and olk14MsgAttach file saves the attachments of Outlook for Mac. Different directories for different items are shown in the following segment:

user_nameDocumentsMicrosoft User DataOffice 2011 IdentitiesMain IdentityData RecordsMessages

&

user_nameDocumentsMicrosoft User DataOffice 2011 IdentitiesMain IdentityData RecordsMessage Attachments

Most of the forensic investigators can easily handle the email files but the olk14MsgAttach files are a little different and difficult to handle. The hex view of the file is shown in the following section and the structure is also described:

Structure of olk14MsgAttach File

The different attributes of the olk14MsgAttach Outlook for Mac attachment file are as follows:

• Attc – This is the signature of the file and the hex value of it is 41 74 74 63.
• Content-type – It defines the file category and applicable application.
• Name – Here, the name of the file is mentioned.
• Content-disposition – It specifies whether the attachment is inline or attached for subsequent access.

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Note – If this attribute contains “inline”, it means that the attachment is displayed when the message is opened. These attachments displayed in the same order as they occur in the message. On the other hand, if the content-disposition displays “attachment” in it, that means that these attachments require actions to be displayed and are placed out of the message part. They are stored to be accessed later.

• Filename – This entity is same as mentioned in “name”.
• Content-transfer-encoding – Always shown as “base 64” because binary file is encoded with it.

The data of the binary file which is encoded begins with “base 64” (hex value – 62 61 73 65 36 34). Then occurs 0D which probably signifies buffer and it can occur several times.

Now, for processing olk14MsgAttach file, users can go for a third party application i.e. OLK Converter for Mac which can be used to transfer your emails along with attachments. The software provides an option to move emails into multiple file formats along with attachments. It can support both olk14 and olk15 message files which makes easier for the users to perform conversion using a single tool only.

Working of Software to Extract olk14MsgAttach File

• Launch the software and click on Add Folder(s) button.
• Browse the OLK files and then press Next button.
• Choose the output file format from various available options.
• Apply filters if you want and then choose the destination location.
• Now, click on Export button.
• When the export process completes, go to the storage location where the olk15MsgAttach and other files are saved.
• Here, you can open and access the attachments stored in OLK file easily.

Conclusion

As discussed in the above section, the hex view of the olk14MsgAttach file is quite different from any other email attachment. Therefore, it becomes a little bit difficult for the forensic investigators to read it properly. To overcome this situation, a user is suggested to switch the file format of the olk14MsgAttach file to some other file format and read it in a proper manner. Thus, to do this, a user is suggested to use a third-party tool which is mentioned above, which can convert all data items stored in OLK file, including attachments to multiple formats. Using this tool, it becomes easy for investigators also to investigate olk14MsgAttach or olk15MsgAttach file in an appropriate manner.

The straight explanation to your 1st issue is that Word documents typically do not have toolbars. If you send a Word document as an attachment it stands to reason that the recipient will open the attachment in Word [assuming s/he has the program]. The toolbars they see are a part of their Word installation & will appear any time they use Word. The only way to prevent that is to complicate the document with VBA that manipulates their copy of the program to hide the toolbars -- Something which most users will not tolerate & may not open because of the macro warning. If they open the Word document using a different program (Open Office, Apple's Pages, etc.), that program's interface is what will be presented.
It sounds like what you would prefer to do is create a PDF & send a copy of the PDF as an attachment. Word does not open PDF files, so the 'toolbars' the recipient sees when they open the PDF are those that are a part of the User Interface of the PDF reader they're using (Apple's Preview, Adobe Reader, etc.). Consequently, neither can Word send a PDF as an attachment. You need to use the features of your email software to attach a copy of the PDF after generating the PDF from the Word document.
To do that you can either use:

• File> Save As then select PDF from the list of Formats in the Save As dialog, or
• File> Print then click the PDF button in the Print dialog & select Save as PDF. If you have Adobe Acrobat, Save as Adobe PDF also will be available when using this option.
• If you do have Adobe Acrobat you may also be able to use it to generate a PDF from the Word document. It depends on which release of Acrobat you have. Note that Adobe Reader cannot create a PDF other than by way of the [fee-based] online service offered by Adobe.
  

BTW: Adobe is the name of a software development company which offers a variety of programs. There's no indication of which of those programs you've installed, but none of them are available as tools in Word, itself. It's a service added by OS X in the Print dialog.
The real problem, then, seems to be in creating a PDF. Unfortunately, you give no description of how you're attempting to do that or exactly what happens when you try. I'm afraid '

Mac Email Attachment

Outlook For Mac Attachment

not able' doesn't give anything to go on. Without detailed information it's impossible to determine what might be the cause of the problem. In general:

1. Make sure you have OS X [10.9.1] & Office 2011 [14.3.9] fully updated
2. Run Disk Utility to repair disk permissions on your HD
3. Restart your Mac

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If you still have a problem generating a PDF using one of the methods described above, please reply here with a full description of what that problem is. Indicate which method you're using, the exact steps you're taking as well as the specific results.