Data Loss Prevention (DLP) Survival Guide - Ashley Knowles
How quickly could you detect sensitive data being exfiltrated?
Join us for a free one-hour BHIS webcast with Ashley Knowles on best practices for data loss prevention and keeping your most sensitive information safe.
You’ll learn about common vulnerabilities, real-world scenarios, and practical, actionable strategies to protect the data you’ve been hired to safeguard.
🛝 Webcast Slides
https://www.blackhillsinfosec.com/wp-content/uploads/2026/02/SLIDES_Data-Loss-Protection-Survival-Guide.pdf
Chapters
Chat with your fellow attendees in the BHIS Discord server:
https://discord.gg/bhis
in the #🔴live-chat channel
🔗 Register for FREE Infosec Webcasts, Anti-casts & Summits –
https://poweredbybhis.com
Click here to watch a video of this episode.
Brought to you by:
Join us for a free one-hour BHIS webcast with Ashley Knowles on best practices for data loss prevention and keeping your most sensitive information safe.
You’ll learn about common vulnerabilities, real-world scenarios, and practical, actionable strategies to protect the data you’ve been hired to safeguard.
🛝 Webcast Slides
https://www.blackhillsinfosec.com/wp-content/uploads/2026/02/SLIDES_Data-Loss-Protection-Survival-Guide.pdf
Chapters
- (00:00) - Intro
- (02:57) - About Ashley Knowles
- (03:26) - Why DLP Shouldn't Terrify You (Too Much)
- (08:10) - Understanding Your Data Landscape
- (10:23) - Data Classification Framework
- (11:49) - Where Does Your Data Live?
- (14:24) - Understanding Data Exfiltration
- (18:34) - Advanced Exfiltration Methods
- (22:20) - The Insider Threat Reality
- (24:19) - How to Stop Data Loss: The Basics
- (25:51) - Technical Controls That Work
- (27:44) - Recommended Layered Approach
- (30:56) - Cloud & Modern Workplace Protection
- (32:01) - The Purple Team Process
- (34:18) - Purple Team Testing: Scenario 1
- (36:38) - Purple Team Testing: Scenario 2
- (39:13) - Purple Team Testing: Scenario 3
- (40:12) - Purple Team Testing: Scenario 4
- (40:40) - Purple Team Testing: Scenario 5
- (42:03) - Starting Your DLP Journey
- (43:50) - Key Takeaways & Action Items
- (44:16) - Questions & Resources
- (55:59) - The "What it's like to work with Black Hills Information Security" segment
Chat with your fellow attendees in the BHIS Discord server:
https://discord.gg/bhis
in the #🔴live-chat channel
🔗 Register for FREE Infosec Webcasts, Anti-casts & Summits –
https://poweredbybhis.com
Click here to watch a video of this episode.
Brought to you by:
Black Hills Information Security
Antisyphon Training
Active Countermeasures
Wild West Hackin Fest
Episode Video
Creators and Guests
Host
Deb Wigley
Deb Wigley is the Director of Kindness and Generosity for Black Hills Information Security (BHIS). She joined the team in 2019 after celebrating 20 years of working in customer engagement and satisfaction in the Automotive Industry. She brings her passion for helping and serving people to the work she does at BHIS. The part of her role she enjoys the most is interacting with the community through our webcasts and educational content, our Discord servers, and conferences. She loves being a mom to her four kiddos and in her spare time, she enjoys reading, hiking, frequently entertaining a beach day, and being whisked away on rewilding adventures with her husband of 20+ years as much as possible.
Host
Jason Blanchard
Jason Blanchard has been happily adopted into the hacker community at Black Hills Information Security (BHIS) since 2019, even though he “works in marketing.” He’s had every dream job imaginable: teaching filmmaking, owning the world’s most famous comic book store, and fostering the infosec community efforts for SANS. While some at BHIS call him the “Director of Excitement,” he is formally known as the Excitement Co-Creator. In his day-to-day work of “sucking at capitalism,” Jason enjoys helping others, sharing his knowledge, and giving away lots of free stuff. When he’s not working, Jason spends time with his wife and daughter, hosts a semiweekly job-hunting Twitch stream, and enjoys writing short stories and performing stand-up comedy.
Guest
Ashley Knowles
Ashley Knowles joined Black Hills Information Security (BHIS) in Fall 2021. As a Security Consultant, Ashley’s role is to perform network (internal/external), social engineering, and cloud penetration tests, as well as participating in red team assessments. Since joining the infosec community in 2013, she has developed and taught hacking classes, worked as a security consultant, and been a team lead on a red team. Ashley serves as a mentor at a local high school’s cyber security class and, as someone who loves to learn and teach, she looks forward to developing and teaching classes that add to BHIS’s educational catalogue. In her free time, Ashely enjoys photography, hiking and exploring new places with her kids, and building Legos.
Guest
Bryan Strand
Bryan Strand began working for Black Hills Information Security (BHIS) in 2017 as a Manager of Business Capture and a Consultant. Prior to joining the team at BHIS, he worked in a variety of fields including psychology, sales, and aviation. Currently, Bryan is responsible for communicating with clients and guiding them toward a better security posture. Bryan and John have known each other for more than 30 years, and when an opportunity became available at BHIS, he couldn’t pass up working with his family. Bryan loves his team and loves helping to create environments that others would want to work in every day. Away from work, Bryan enjoys reading, being outdoors, and spending time with family and friends.
Producer
Ryan Poirier
Ryan Poirier began his time at Black Hills Information Security (BHIS) as the Video Producer and Editor in August 2020. Ryan polishes and perfects every webcast, podcast, and workshop on the BHIS, ACM, and WWHF YouTube Channels. Prior to Ryan’s time at BHIS, he worked for one of the largest public schools in the United States, conducting their video production and live broadcasting. He joined the BHIS team because he felt like it would be a great group of people to work with, and he couldn’t pass up the perfect next step in his career. Outside of his time with BHIS, Ryan does freelance photography, attends Cars & Coffee events, and expands his knowledge of audio and videos.