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Email Management, Part 2

Two (More) Dangerous Outlook Features for Lawyers

By Deborah Savadra

Just because nearly everyone knows how to send email doesn’t mean they use it well. In my previous post (“Most Dangerous Outlook Features for Lawyers“), I showed you two frequently used Outlook features that trip up even seasoned users: Auto-Complete and Out of Office (aka Automatic Replies). Here are two more features you’ll want to be wary of, lest you accidentally breach attorney-client privilege.


Blind-copying a client on an outgoing email seems like an efficient way to keep a client or other interested party in the loop on your communications with opposing counsel or others. Outlook keeps the identity of any BCC’d parties secret in your outgoing email (although they’re still retained in the message’s metadata). Sounds safe enough, right?

The problem with BCC, however, isn’t your outgoing email. It’s what happens when a blind-copied recipient hits Reply to All. At that point, one protected recipient’s identity is exposed, and if others on the BCC list do the same, their identities are revealed as well as what they wrote.

I’m not saying it’s always dangerous to use BCC. For instance, if your assistant saves your outgoing emails to a document management system, blind-copying him or her makes that task easier. If you use BCC, though, always consider the impact on client confidentiality should the reply chain get out of your control.

In some cases, you would be better off forwarding the original message to your client (with a slightly altered Subject line to keep it out of the original Outlook conversation view).

Reply to All

Decades after the invention of email, Reply to All still wreaks havoc. And if an email has a particularly long list of recipients, everyone’s inbox can fill up quickly.

Fortunately, this feature can be disabled or at least modified. Here’s how:

1. Disable Reply to All on your outgoing messages. Microsoft offers a plug-in called No Reply All that adds the option to disable a recipient’s Reply to All function on your outgoing message. It’s not 100 percent foolproof, though, because it depends on your recipient using Outlook to honor the flag this adds to your email. For something more foolproof, talk to your IT person about what settings can be tweaked on your Exchange Server.

2. Get a warning when you click Reply to All. Sperry Software offers a plug-in called Reply to All Monitor that pops up a warning whenever you click Reply to All. It can even prompt you whenever your reply is going outside your firm or if you were BCC’d on the original email. That moment you stop to think “Should I or shouldn’t I?” could save you lots of embarrassment.

Bottom line: Always use email mindfully.

Illustration ©iStockPhoto.com

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Deborah Savadra Legal Office Guru Deborah Savadra

Deborah Savadra spends a lot of her time explaining technology to lawyers, mostly as editor and chief blogger at Legal Office Guru, which features Microsoft Office video tutorials and other content especially for legal professionals. Watch her quick tips videos here, and follow her on Twitter @legalofficeguru.

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