Trying to prevent data leakage. Especially when laptop is out of office.

We are trying to lock down our data to prevent leakage.  I'm not taking about un-authorized access.  I'm talking about making sure that data that people are authorized to access doesn't get into the wrong hands ... such as competitors.

I can lock down my firewall to prevent access to certain sites.  I can block webmail internally.  I can restrict email ... somewhat.   But at least I can see what was sent to who.

However if a file is on a laptop and the laptop is not in the office, how can I prevent them from emailing that to someone via webmail?   Or downloading to a web site?

Also relative to data leakage.   We have folks that may travel and occasionally need to visit the business center of the hotel to print documents.   We have disabled the use of USB drives because of security concerns.  If they use OWA, that will let them print, but it leaves a thumbprint on the PC.   And it also gives the ability to leave the document open or download the file without us knowing about it.   I've tried to find ways to open and print, but not allow them to save, but have been unsuccessful at doing so.  When I restricted via HTML access only, the formatting was all messed up when we tried to print it.
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I don't think you can prevent them emailing others. But there are other precautions you can take. First make your users sign an agreement where they don't do any such things. To this agreement also have things added like they need to take care of the laptop, and that they don't expose passwords etc to others.

Besides that, use the laptop's builtin security options, like BIOS and HD password, so that the user will have to enter a password whenever he turns on the laptop, before it actually starts booting, and so that the HD is unusable without the PW being known. It would also make sense to use encryption. That way, if the laptop gets stolen, the disk and the laptop will be useless to the crook.
btanExec ConsultantCommented:
Data leakage largely focus on the channel via email, web, file, mobile and device. Looks like the email and web are within the control. File and device (like USB and wireless) are probably area to tighten if desired via application whitelisting , application control and device control. Windows GPO or even Host intrusion prevention s/w does that. Esp USB drive, that is one that should allow only authorised org device issued and not bring in personal one if poss. Likewise the mobile, MDM and MAM must come in and interface to cloud service such as dropbox,, should be checked via proxy.
For remote user, ideally they can established VPN to reach web and other resource. That itself, the HIPS can enforce it with location awareness (such as Symantec SEP) whereby the policy enforce stricter off site FW rule. Also lockdown the browser proxy to go via the internal proxy to allow surfing. If necessary, wireless SSID whitelisting (meaning profile created created as part of machine provisioning) can be considered.

For the hotel OWA access, it is the RMS for outlook (or email) client to look into instead. For specific ADRMS policy template, you can check out this which you can customise a template instead of using the default "Do not Forward". But do note this
IRM can’t prevent content from being erased, stolen, corrupted, or captured and transmitted by malicious programs or computer viruses. It also can’t prevent restricted content from being hand-copied or retyped, or prevent a digital photograph or screen capture being taken of the restricted content.

Also do not give user the Admin right in the login as privileges overrides policy and rules. Enforce audit trail to policy/object changes which can deter at times users to be more wary of their action

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Schuyler DorseyCommented:
I think your focus for this issue should be on endpoint security - specifically GPO and security suites.

E.g. GPO and AV security suites like Kaspersky and Symantec can lock down USB ports and prevent flash storage.

They can also do web filtering on the host itself. So you can configure Kaspersky for example to block access to personal webmail sites.

You obviously want to ensure the laptops are using full disk encryption as well in the event they are stolen. Kaspersky or Symantec can take care of this too.

And lastly, look into endpoint DLP products.

If your company email is Exchange, it has DLP features built in you can try utilizing as well.
btanExec ConsultantCommented:
To add...Indeed endpoint lockdown is key and if user is given admin right, they can simply bypass and leak info. Imagine if they have dropbox and can be installed to file sync with their personal account as well as business account, such bridging leads to leaks that can be intentionally or unintentionally.

DLP can be at the point of egress and ingress on critical services such as network segment, email services, file, database and web services since they are most of the times holding those crown jewels. Least privileged principle, remove remote admin and access, segregate high risk and low risk service segment, endpoint/appl/ext device lockdown checks and audit trail can deter and help reduce exposure.

There are even anti-theft mechanism in endpoint and remote wipe in event of device loss or total wipe out for revocation. But to proactively alert for leaks will be good to consider even external crawling or social services scouting for organisation leaks in underground and public forum and social media sites..
Ashot OganesyanCommented:
Use DeviceLock DLP to control local devices (USB, FireWire, etc.) and network resources such as drop box, google drive and so on.
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