Secure Zip Outlook Attachments

[Orville Marquez]

Tuesdayafternoon, several of our end-users are reporting issues with Outlook attachment handling when ESET Endpoint Security v 10.0.2045.0 is installed. Outlook locks up when attempting to save, preview or view attachments. We have tested PDF & XLSX attachments, both file types have the same issue.

I was having the same issue and found that Windows Defender was not turning off with Eset installed. Once I turned off Windows Defender through group policy (or local security policy in a workgroup) to I have no more issues.

I am having a similar issue with v10.0.2045.0 causing a 10-15 second slowdown when previewing or opening any attachments in Outlook 365. Disabling real time scanning or pausing all protection is the only way to alleviate the issue. Disabling client email integration does not help, nor does disabling Defender via PS command or GPO, full reinstall of Office/ESET, different Outlook profiles or safe mode. I eventually landed on disabling the real time scanning of outlook.exe, while still leaving all email client integration enabled, and attachments load with speed now.

Email is a very important channel for people to communicate in life and work. Many crucial and confidential data documents, from trade secrets to personally identifiable information need to be sent by mail to achieve a purpose as the attachments.

However, mail clients do not provide the most secure protection for users' mail information. Email security measures such as strong passwords and 2-step authentication are not enough to provide lasting protection for your data. Only encryption, which scrambles your data so it can't read it without the right password, can completely isolate information from common threats, such as phishing attacks, malicious insiders, or simple employee errors.

So, how do you send an email with attachments securely in Outlook, Gmail, or Yahoo? Password protecting the files is a great way. But how to encrypt the Word, Excel, PDF, photos, or other document attachments in email? It depends on the attachment you send. We will introduce several simple ways to help you password protect email attachments and send the email securely in this post.

Email providers typically have a limit on attachments, for example, a maximum file size (25MB for Gmail). Therefore, when we have multiple files to transfer as email attachments, we always choose to compress them before sending them.

In fact, you can encrypt files during the process of compressing them. In this way, when it is sent as an attachment, it is protected by a password. You only need to tell the recipient of the unlocking password so that the recipient can browse the file smoothly without being spied on by irrelevant people.

Once the compression process is completed, you'll get a password to protect the zip file. After attaching the Zip file and sending in the email, you will need to provide the password to the recipient later to unzip the file.

If the email attachments are Microsoft Office documents, like MS Word, MS Excel, or MS PPT, you can apply the inbuilt password protection option to encrypt documents with passwords, and then send a secure email.

Based on the files you want to use as email attachments, you can take different solutions provided above to password protect email files and send them safely. You can use a file zip tool to compress and encrypt a zip file, or you can use the MS Office password protect option to secure Word, Excel, or PPT documents.

I have been enabling various DLP's at our company in test groups, I have them working well in terms of what data is getting flagged. However in Outlook 2016 if a user selects attach a file the prompt comes up but if they drag and drop the same file in a new email the prompt does not come up. I know this has to do with Outlooks Temp Secure folder which the location can be found in the registry at these locations-

I believe we have a reported issue with file not being flagged during drag and drop action in Outlook 2016. It would be great if you could open a support ticket and then PM the case datils for further follow-up.

Already did lol, I opened one with Sophos and one with Microsoft, I will paste my open response to where I am at with Microsoft below, in regards to Sophos I am scheduling a remote session with them currently to look further into the issue.

I have attempted this again, without AV, with AV, newly installed outlook & re-completed the registry changes in the GPO just to be sure, basically I started from scratch. The computer was fully updated running the latest Outlook/Sophos and Windows 10 Pro Updates.

I have then ran gpupdate /force and or logged in/out and or restarted the computer to apply the registry changes, (Double checking each to make sure there is no difference) the registry changes are applied, I can confirm this by checking the registry via regedit. Once I have had them confirmed I opened procmon, then opened Outlook. At this point I did not see anything changing the secure folder location in the registry, I refreshed and even reopened Regedit to make sure the folder path had not changed and still was C:\Users\%username%\Desktop\Outlook, I then opened a new email and again nothing changing, repeated the process of reopening regedit to confirm, however once I drag and drop an attachment into an email.

Also after reading through a few other forums on Sophos Community I have found that this issue also occurs if a user right clicks a file and uses the send as option built into Windows, the file is attached and DLP does not prompt anytype of alert status.

Mishandling sensitive information can also result in fines and other penalties for those in industries such as finance, legal, publishing, education, and healthcare that have to comply with data protection laws like HIPAA or GDPR.

In 2019, cyber criminals hacked webmail client Outlook.com and gained access to sensitive private information, including email subject lines, folder names, contact lists, and some email content. Using end-to-end encryption is the only way to make sure that your Outlook email messages and attachments are entirely secure, both while in transit to your recipient and sitting at rest in an inbox.

Control access to your email attachment anytime after sending it and choose if your recipient can download or print it. Add a watermark and set your document to self destruct after a specific amount of time. You can also see how many times your document was viewed and for how long.

When your recipient receives your encrypted email attachment, all they have to do is click on the attachment link within the email. Your Outlook email attachment can then be viewed via a secure Digify link.

You can also select if you want the recipient to verify their email address to open the attached document. When you choose this option, a code is automatically created and sent to your recipient so they can open the attachment.

As the most popular business communication method, organizations rely on email to send sensitive documents such as contracts, presentations, and many other types of files. Once you send an email you have to guess where your attached documents end up and if they were even opened by your recipient.

You can see when your recipient opened your email and attachment, how long they viewed them, and if they downloaded or printed your document. After a set amount of time, you can configure your email and attachment to automatically expire.

This way you never have to risk your confidential information being exposed to the wrong person or organization. Simply click a toggle switch to revoke access after the Outlook email and attachment has been sent to your recipient.

Data breaches disclosed 4.1 billion records in the first six months of 2019. Even though data breaches are becoming more common every year, many companies are not prepared to prevent and combat them, thereby putting themselves needlessly at risk of both reputation and financial loss.

Fortunately, you can boost your email security against breaches with email encryption solutions like Digify. Now you can regain control of who has access to your Outlook emails and attachments without sacrificing seamless collaboration.

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Using Box for Microsoft Outlook is simple and fast. Box for Outlook brings your secure Box content repository directly into your Outlook interface, enabling you to store email attachments and messages directly into the Box folder of your choice. It also enables you to insert shared links to your Box files anywhere within the body of your email message, so you can share your Box content with anyone you wish while fully retaining any security policies that exist around the actual files.

Box for Outlook is a Microsoft add-in you install and deploy like other Outlook add-ins. You can install it yourself, if it's not blocked by your organization's Microsoft Office administrator. Or your admin could make the Box for Outlook integration available via an enterprise-wide deployment. If that is the case, when you open Outlook and create a new email message you see the Box icon below the body of the message on the right, in the third-party application bar.

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