Sending Large PDF Documents By Email

Published in 2011
by Christopher B. Hopkins

Email has become the dominant communication medium for the legal profession – drowning out faxes, overnight mail, and even the humble phone call – yet delivery of large PDF documents via email remains an impediment. Adobe PDF has become the default standard for discovery since it provides a fixed (largely un-editable) depiction of an image or document. Law firm scanners are typically set at fairly high detail settings which, in turn, creates larger PDF files that are often blocked by email restrictions. Sending PDFs or other large files in excess of 5mb may never reach the recipient and warning auto-replies (“there has been a delay in sending your message”) add to the uncertainty.

Solutions exist at several levels with two fairly simple workarounds at the end-user level: (1) create smaller PDFs or shrink existing ones and (2) use free services to email links to the documents, rather than the documents themselves, to avoid email caps.

Create Smaller PDFs

If you frequently scan documents to PDF or save Word documents as PDF, consider setting the quality or dpi standards to lower settings such as “email size” or 300 dpi. Scan or save PDFs at varying quality settings to see if you can tell the difference. Often the minimum setting is sufficient for document delivery and reading. If using a scanner, Google the name of the scanner and “quality” or “output settings” to determine how to adjust the settings. Black and white is preferred since color adds significantly to the PDF file size.

In Word 2007 or higher, save a document as PDF by selecting Save As and then PDF or XPS. Look for the “Optimize for” button underneath the file name and select “minimum size (publishing online).”

Shrink Existing PDFs

The free Adobe Reader on most of our computers allows you to open but not edit (only “read”) PDFs. Again, the purpose of the PDF format is to create a fixed image of your document. Thus you will find that shrinking existing PDFs is a “workaround” rather than a standard function unless your office has the (paid version) of Adobe Acrobat. Open your oversized PDF, choose Print, and select printer named “Adobe PDF” from the drop-down list. It does not give you options for quality settings but this trick should reduce the file size. Follow the steps to re-name the document and you should have a reduced copy of your PDF.

For great control, consider free tools such as PDF ReDirect, Free PDF Compressor, doPDF Free Converter, PDF Compress, PDF-XChange or PDF Shrink. Go to and read the reviews to select the best option for you. Mac users have an easier time: open the document via Preview in the Applications folder, select Save As and chose Reduce File Size.

Emailing Large PDFs

There are several online services which allow you to send large PDFs via email. Most of these have free options which are limited by size and the number of documents you can transmit per month. If you send large PDFs only occasionally, the free accounts should be the way to go. Note my caveats at the end of the article.

DropSend is a service which allowed me to sign up and send a document in less than a minute. While there are paid accounts with nearly unlimited restrictions, the free account allows you to send up to 2gig and five “sends” per month. Go to, give your email address, the recipient’s email address, and link the PDF document. You can create a short email message and title. The recipient receives an email from you which gives them a link to download the file.

DropBox also provides this same service as well as the ability to save your own private documents to “the cloud.” In short, you can use DropBox to save files online and then pick them up from your laptop, iPhone or even someone else’s computer – a handy tool if you are traveling. DropBox also gives you a public folder so you can upload your PDF and then give someone the direct link to download. Go to and watch the short video – you will be up and running in 5-10 minutes and likely will use the service for more than just emailing large files. is another established file-delivery service which provides free and paid options. Free accounts are limited to 100mb per email and you cannot send multiple files and folders.


Two words of modest caution when sending PDFs via these delivery services. One, you are sending PDFs to a third party which is then sending a link to your recipient. If there is concern about using “cloud” services or sending files via third parties, this may not be an option. Still, if the PDF is appropriate to be sent via email then this is an equally safe alternative. Two, sometimes these services’ email can appear to the recipient’s domain as spam – copy yourself on the email and re-send the link directly from your account to ensure receipt.

Christopher B. Hopkins is a shareholder at Akerman Senterfitt. You can test the firm’s email size restrictions by contacting him at

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