Paperless Tip: Never Ever Send Word Files as Correspondence

Letterhead

Never ever ever send a Word file as “correspondence.” A Word file — or a WordPerfect, OpenOffice.org, or Pages file — is not a document. PDFs are documents. Word files are drafts. And sending a draft that includes your digital letterhead and signature to anyone is just plain stupid. Here’s why.

I frequently receive “correspondence” attached to an email from an attorney involved in one of my cases. Nothing is unusual about that. While I think an email with a professional-looking signature block is plenty formal, there are times when a more formal letter is important, and sending it as an attachment to an email works just fine. What is unusual is how these attachments are sent to me — as a Word file instead of as a PDF.

Okay, first thing to take away: Word files are not documents. In a paperless environment, a document must be a substitute for the actual paper. A PDF file can be a document. A Word file cannot. Write this down. Word files are drafts. They are never ever final documents.

Why? Because by their very nature anyone you send them to can change them! That all-important not in your letter can be deleted and the doctored letter used against your client — as in “My client did not steal $100,000 from your client” becomes “My client did steal $100,000 from your client.” See the problem?

Word files are simply not final documents and should never be sent to anyone unless you are working on a draft.

What I usually receive is a .doc file with the firm’s digital letterhead and the content of the letter. In each case the “signature” of the attorney was simply their name preceded by /s/. First, this is the lamest way to “sign” a document outside of electronic case filing, what those attorneys did was provide me with a template to create correspondence from their firm, if I was inclined to do so. (Obviously, I would not, since it would be an obvious ethical violation.) You should not expect everyone you deal with to be scrupulous. In fact, you should assume that they will be unscrupulous to protect yourself and your client.

The second thing to take away from this is that many, many attorneys still have no idea how to operate in an increasingly paperless world. Many state courts are converting to electronic filing. Attorneys who do not understand the basics of a paperless practice will not be able to navigate in that world.

The bottom line is this: sending a Word file to an attorney is fine if you are in fact collaborating on that file. But always remember that the Word file is not the final product; it is only a draft and you should never treat it as anything else. Protect your digital signatures and digital letterhead as you would physical versions. You’ve never sent your opposing counsel a stack of your blank letterhead have you? Then don’t do it digitally.

This was originally published on April 25, 2013. It bears repeating, so we republished it on August 25, 2014.

Legal Technology, Practice Management

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  • http://www.linkedin.com/in/matthewsalzwedel Matthew Salzwedel

    All correct points, except that your advice also applies to paper offices.

    You also omitted another important reason why you should never send a Word document outside of your office: The embedded track changes (if you forgot to accept all changes) and other metadata that could give opposing counsel or a competitor a nice peek behind the curtain.

    E-mailing letters/briefs/contracts in Word outside the office is a malpractice claim waiting to happen. It’s not rocket science: (1) Create letter in Word; (2) Save (or manually scan) as PDF; (3) E-mail PDF.

  • http://elliott.io elliott

    Aren’t PDFs also technically “editable”? What precautions are people taking to not allow those to also be tampered with?

  • http://www.avifrischlaw.com Avi Frisch

    I would say that the same thing actually applies to PDF’s as well, since they are fairly easily modified. If one is intent on forgery and manipulation of documents they can easily do so. Now, it might make sense to make it more difficult, one can do the same with a paper letter scanned into a computer.

  • King Bradley

    All your points are correct in my opinion, exactly as Matthew Salzwedel’s.
    I dare to add my supplementary two cents: if you really do send an editable file via e-mail, you still have (and can save) the e-mail you sent, which includes the exact version of the editable file you attached. Thus, if someone ever claims that you’ve sent the doctored file, you still have the e-mail which includes the genuine attachments.
    As for the blank letterhead, it is way too easy to forge that both in the paper and paperless world, even from a PDF file, to blame it on the editable files sent via e-mail.

    • Kirk

      You’re mostly right, but I could just as easily edit your email in place to doctor it with whatever content I want. Need me to forge the email logs? Ok. I can do that to.

      The only way around this is to digitally sign every document leaving your office. It’s (for all practical purposes) impossible for forge a digital signature, and editing a signed document invalidates its signature.

  • http://www.ginsbergshulman.com/ David Shulman

    All good points, but you forgot the other reason why you need to send PDFs and not Word files — Formatting.

    I have people send letters as Word files all the time, and they look like crap. Their fonts and spacing and whatever don’t carry over, and it just gives off an unprofessional aura.

    • http://lawyerist.com/author/samglover/ Sam Glover

      Which also gets at why it’s really not all that important to use Word in the first place. Make the documents you turn into PDFs in whatever software you like.

  • Chris Sandervous

    It really is about understanding metadata. Until one understands metadata, all formats will be drafts. It takes just a few clicks of software to locate and edit metadata of PDF files and to edit them. The software for editing and securing metadata can be found with a simple search. The software is available for free and is open sourced.

    I would urge consideration of the use of encryption. I have found that insistence on the use of PGP encryption is a more secure way to handle all files and it is free. There is sometimes resistance to it’s use, but once properly explained, those interested in secure transmission will accept usage. Encryption also helps to reduce the number of contacts with the material as people tend not to want to share encryption keys unless absolutely necessary which lessens the chance of malicious editing.

  • Todd Hendrickson

    Great points from all. Yes, ultimately a .pdf or even an actual paper letter can be forged. But I think it is a matter of degrees of security. Anything can be forged, but it takes work. Sending a Word .doc is like sending a blank, signed check. You just don’t do it.

  • Ebony Jones

    This is probably one of the most valuable bits of information I have EVER received!!! Woe is me who couldn’t figure out why everyone wants files via PDF now. I am soooooooooo glad I just read this. I will NEVER send a “document” via WORD again.

    Thank you.

  • http://www.maciaslegal.es/ jose ignacio macías

    Absolutely right. No lawyer should ever send a document in open format, though I know a couple that do so. It sshould be a PDF file and DIGITALLY SIGNED!

  • http://www.paulrpalmer.com Paul Palmer

    I agree you shouldn’t send word documents. I also agree with the use of PDF, but not in text format. Data encryption adds security not exporting to PDF format. I have the latest adobe suite which allows me to edit most PDF files. In addition if a PDF is locked I have another program to extract the content when it has been created in text format. It only takes a few seconds.
    The best secure transmission I am aware of is using PKI data encryption with a remote verification service.
    The method I use though is print sign and scan as the content is harder to extract.

    Paul Palmer

  • http://Www.vuttonassociates.ca Veronica Utton

    Actually, Word docs can be locked with a password to prevent unwanted edits and, the latest version of adobe now enables PDFs to be re-formatted to word docs, which can then be edited. Personally, I’m not convinced that paper docs will completely disappear.

  • http://www.prompt@promptconsulting.com Francine Millman

    One thing I ALWAYS make sure to show attorneys when teaching them about PDFs is that most PDFs are VERY easily editable. I take a very simple PDF and can add the word “no” to the sentence (or something else to change the meaning) and it changes the entire context of the paragraph or document.

    I also show them how easy it is to add new text and no one would ever know.
    Then, I watch their eyes get wide, their mouths drop open and I wait a few moments for it to really sink it.

    They tell me they were told that PDFs can’t be edited and I remind them that they were probably told this when Acrobat first came out. Now, 20+ years later – and because of demands of application users – you can.

    Then, they get it.
    Then, we talk about securing PDFs. Some immediate incorporate those steps when appropriate and others ask me to teach their secretary so that they know how and what to do.

    It is always a very enlightening class.

  • Harald

    Don’t exaggerate. Also from a pdf you can create a digital letterhead and a pdf that looks like an original. Not sending a Word file provides no protection. A better option is Adobe Professional’s digital signature feature.

  • I’m no expert, but . . . .

    This is a good opinion piece, but is far from being factually correct.

    Now I’m no expert, but I know enough to question the purported expert advice of this article. Despite not having twenty-five years of practical experience, I would have brought the following to the author’s attention before publishing:

    (1)
    http://www.adobe.com/ca/products/acrobat/editing-pdf-documents.html

    (2)
    http://office.microsoft.com/en-us/powerpoint-help/protect-your-document-workbook-or-presentation-with-passwords-permission-and-other-restrictions-HA010354324.aspx?CTT=1

  • Christine Lara

    How is a PDF file safe when one can convert PDF files to Word? As a teacher, I use PDF to Word frequently when I need to use one section of a PDF file on a Word document, such as pasting a state standard onto an assignment.

  • http://hopebeyondtrauma.com/ John Hatten

    I’ll remember this: thank you.

  • Dawn

    Word documents can be made to be “read only” so only the author can make changes with a password.

  • http://www.stlpersonalinjury.com Todd Hendrickson

    I’m flattered by all the comments and opinions. And much of what is said is true. PDFs are not inherently secure. They can be modified. The same thing can happen with a scanned physical document. You may have to go through a step or two to accomplish it, but it can be done. My point is simple–Word files should never be sent as documents. They are drafts–easily editable. Your work can be modified in any format–just don’t make it so damn easy for someone to do it.

    • http://lawyerist.com/author/samglover/ Sam Glover

      More importantly is the formatting problem. Word docs look different to everyone. If you want your documents to look right, send PDFs.

      Also, a pet peeve of mine (directed not at you but at half the commenters on this post): Adobe is a company. Acrobat is software. Besides, if a single software package were going to be the stand-in for Adobe, I would think it would be Photoshop, not Acrobat.

      • Sheila Baldwin

        Sam, can you explain this comment, “if a single software package were going to be the stand-in for Adobe, I would think it would be Photoshop, not Acrobat.”

        • http://lawyerist.com/author/samglover/ Sam Glover

          The company is probably more well-known for Photoshop, not Acrobat.

  • Kim Van Vliet

    It is now possible to convert from PDF back to a word document using Adobe. This includes documents that have been sent to others.

  • Colin

    Not trying to burst the technophile bubble, but in all practicality, any PDF can be edited in the same way. I negotiated a contract with opposing counsel over email/phone, and his final draft was a copy and paste version of the previous ones, with new lines spliced in, which was pretty seamlessly edited with a basic photoshopping program. Even though I did keep the entire email chain of our discussions, as well as the signed original, he could still change the final document and present it as evidence in a dispute, and say that mine is the doctored version, or that I shredded the true original and deleted the email, etc. Now imagine that scenario playing out if I had used an /s/ to sign my name, or some wacky robo-signer. If the ethics rules, threat of court sanctions, and the inner conscience don’t keep your opponent from doing this stuff, then PDF can’t save you.

    It’s probably better just to print it on your letterhead, physically sign it in ink, and mail it certified if you are worried that the other side is going to play dirty.

  • http://www.avifrischlaw.com Avi Frisch

    If you are worried about forgery then you should not be having business dealings with the person on the other side. There is no way to protect yourself from people willing to commit felonies to get their way. I agree that final documents should not be sent as word format, especially because of the formatting issues, but not because it will prevent a criminal from acting in a criminal way.

  • http://www.globalreach.org Fred Kovach

    I am not a lawyer, but I am an Internet Media Technician and also the website coordinator for Globalreach.org, a website run by Global University, a distance ed school.

    On Globalreach.org, we offer our non-degree courses for download without charge and have had similar concerns as expressed in this article. While we allow printing of our courses (as if we could control it!), we are concerned that someone could alter the text to read something other than we intended.

    We have placed a modification password on all of our documents on globalreach.org (you can feel free to download and experiment with what you can and can’t do if you wish), but still allow opening and printing.

    I just checked and found that I was unable to produce a word document, nor am I able to modify the text using Acrobat Pro 9.0. The error I was given (on producing a word document) was that the document’s permissions would not allow it. The function for “Touch-up Text” is simply not available for secured documents.

    You can also secure a document with your digital signature. Double-clicking the signature box then indicates whether or not the document has been modified, providing additional assurance. I am sure that with almost everyone here being lawyers (except me), that someone could come up with a statement below said signature that indicates the tamper-proof status of the digital signature, and that if it isn’t there, then it may have been modified after it left your office. You could also include a statement that any other file document format than a digitally-signed PDF (such as Word, etc) constitutes an unauthorized draft which may not be substituted.

    Perhaps ,then, (not sure, since I’m not a lawyer) such due diligence would help protect your practice.

    In my experimenting, I found that a signed and locked document will export an image file, with the signature box (but which was unclickable for the security assurance). And a Word document could be exported, but without the signature box. This would be a security concern, but perhaps with the above wording below a signature box, maybe such concerns would be alleviated.

    Maybe one of the lawyers on this thread could write such a statement that would hold muster. I, for one, would love to see it and it would be a service to us all, especially as we navigate our way to paperless offices.

    Fred

  • http://ayrlaw.com/ Steve Ayr

    I’m late to the party on this, but I recently got an offer of settlement from opposing counsel emailed in Word format and it made me think of this article. Not only was it a Word document, but track changes was turned on so I could see all the recent edits opposing counsel had made. In this case there wasn’t anything truly enlightening, but with an offer of settlement like this , such a mistake could have easily revealed something about their thought process that would have prejudiced their client.

  • http://www.promptconsulting.com Francine Millman

    There really isn’t any “looking” that needs to take place to see Track Changes in a Word document. As a precaution, Microsoft automatically displays any track changes to someone who opens a Word document with the Track Changes to prevent such occurrences from happening. In other words, the person who sent the email with the Word attachment probably had Track Changes on when s/he opened the document, changed the view to see the document in Final – and forgot to check when attaching and sending the document to make sure they were removed/accepted.

    It is rather odd in this day and age that a law firm/attorney wouldn’t have a metadata scrubber, but I suppose many cancel the function at the sending stage when they are feeling confident they have done everything properly. We all know how that goes. :)

    So, no real issue of anyone getting in trouble for “looking” for info – it’s right there in your face when you receive it, if someone doesn’t double check to make sure they cleaned the document first.

    • http://lawyerist.com/author/samglover/ Sam Glover

      Look, you and I may not think of it as “looking,” but that won’t stop ethics boards from trying to prohibit it.

  • Wayne

    I’m pretty sure that Safari allows you to save PDF files as text files, which of course could be very easily used with a little formatting.

  • lynz

    Not a lawyer and clearly very late to this article but I always PDF my word documents that are important documents. With that said, there are programs out there that allow you to edit PDF documents and/or put them back into a Word format to edit. I have to do this quite a bit.

  • Mike

    Just so you know there are commonly used PDF editing programs that can edit text of a PDF just as easily as word can edit a doc file. Bluebeam can do it and the end result looks exactly like the original except for the changes you made to it, meaning unless you compared the original word for word, you probably wouldn’t notice the difference.

  • Landon Ascheman

    Given that PDFs can be so easily edited, there is a second part to remember. 1) Always send PDFs not Word files (for the points mentioned, more difficult to edit, and less metadata) 2) Always save your e-mails

  • http://samglover.net/ Sam Glover

    The problem with the “PDFs are so easily edited” comments is that it is usually pretty obvious when a PDF has been edited. (I doubt many of the people in these comments have actually tried to do it, or they would know that.) Also, in order to edit a PDF, you need software for editing PDF documents, and most people do not, because most people never need to edit PDFs. But everyone with a computer can edit a Word document.

    The other reason not to send Word files is that they look different on every computer. PDFs do not. That is why you can call a PDF a document in the sense that it is an actual copy of the original, but a Word file is always a draft.

  • http://thedroidlawyer.com/ Jeffrey Taylor

    Securing files was mentioned briefly, but not in depth. I think folks forget that you can lock a PDF file so it’s not editable. I send all my PDFs with a password required for changes. The end user can still print, but you can’t copy the text or make changes to the document

  • Kimberly Rotter

    I can’t say with 100% certainty, but I believe /s/ is a throwback to early word processing programs that were DOS based. I remember in the early 90s we ran SAMNA in an IP firm where I worked and we had to use codes like that to insert the letterhead, the addressee, the Re: line, any bold or italics, the registered trademark symbol, and of course, the electronic signature. It was all very advanced at the time.

  • Ben W

    Sorry, but, this is just plain wrong. PDFs are easily converted into Word documents, edited, and converted back. The software to do so is cheap and readily available and anyone who thinks or suggests otherwise is clearly not up to date on what exists in the market place. A Word file is every bit as much a document as a PDF. If you take it to court, either one will require authentication, period.

  • tetonattorney

    For important docs, one easy way to address the concern about PDFs is to print the letter and then scan the physical paper copy of the letter. Don’t use the save as PDF option. While there is optical character recognition software that will aid in editing the letter (if the other side really wanted to), it should be very obvious if they do to your microscopically askew, barely wrinkled scan of the original. Plus you remove the meta data in a pretty foolproof way.

    • http://samglover.net/ Sam Glover

      Just note that this significantly increases the file size, which is why courts don’t want you to do this for electronic filing.

  • http://www.texasemploymentlawblog.com/ Christopher McKinney

    While it might be possible, it is not easy to convert an encrypted, password protected PDF to Word or to otherwise change the document. So password protecting PDFs before sending is a best practice that we all should follow.

    But nothing is perfect. Even if password protected, it would be easy enough to print, scan, convert to Word, alter and convert back to PDF if one really wanted to try to fake a document. But those types of changes or document falsification will almost certainly show up in the metadata if there is ever a dispute about whether the document looked a certain way when you sent it out.

    But I agree that sending a word document is a bad idea. Beyond the issue of how easy they are to edit is the fact that they don’t transfer well. We don’t even use Word in our firm so if you send me a word document, I’ll be opening it in Google Docs and while it will work, the formatting might get screwed up.

    The exception to this is I think the situation when you genuinly wish to collaborate with someone on a document. Word files aren’t great for this but MS’s new Office360 online version of Word is better. GDocs still is the best solution for this type of collaborative work imho.