Risky Business Podcast

Analysis and news podcasts published weekly

Risky Biz Snake Oilers: Mike Wiacek launches Stairwell, Red Canary on modern MDR and Datadog pitches full stack monitoring

Presented by

Patrick Gray
Patrick Gray

CEO and Publisher

In this edition of the Snake Oilers we’ll hear pitches from three vendors:

  • Stairwell! A new startup from Chronicle Security co-founder Mike Wiacek
  • Red Canary explains what modern managed detection and response looks like
  • Pierre Betouin from Datadog talks about the challenges around bringing together DevOps and Security while providing full-stack security

Links to everything we talked about are in the show notes.

Risky Biz Snake Oilers: Mike Wiacek launches Stairwell, Red Canary on modern MDR and Datadog pitches full stack monitoring
0:00 / 44:30

Risky Business #640 -- Huh. The CIA really was out to neck Assange

Presented by

Patrick Gray
Patrick Gray

CEO and Publisher

Adam Boileau
Adam Boileau

Technology Editor

On this week’s show Patrick Gray and Adam Boileau discuss the week’s security news, including:

  • The amazing Yahoo! News story on the former CIA director’s awesome brainwaves
  • Hostage diplomacy pays off for Huawei CFO
  • NSA releases great guidance on VPN security
  • Microsoft has actually hired a cybersecurity executive
  • Much, much more

This week’s show is brought to you by Material Security. Material’s co-founder Ryan Noon will be along in this week’s sponsor interview to talk about smarter ways to do email retention and destruction. They have a product that interfaces with your mail provider’s API – whether you’re on Google Workspace or O365 – to do things like archive and redact email, and they’re finding their customers are using these features to actually implement retention email strategies.

Risky Business #640 -- Huh. The CIA really was out to neck Assange
0:00 / 68:05

Risky Business #639 -- USA's ransomware non-policy fails to meet its unstated objective

Presented by

Patrick Gray
Patrick Gray

CEO and Publisher

Adam Boileau
Adam Boileau

Technology Editor

On this week’s show Patrick Gray and Adam Boileau discuss the week’s security news, including:

  • BlackMatter is back in the USA’s critical supply chain
  • The FBI and friends apparently got up in REvil’s business
  • The Azure OMI thing is totally the disaster we were expecting
  • Much, much more

Brett Winterford is this week’s sponsor guest. These days Brett is a senior director of cybersecurity strategy at Okta, but the reason you might recognise his name is because he took a year off working for vendors to be our newsletter author – he was the founding editor of the Seriously Risky Business newsletter.

He’ll be along to talk about legacy auth and why vendors should have deprecation policies.

Risky Business #639 -- USA's ransomware non-policy fails to meet its unstated objective
0:00 / 63:19

Risky Business #638 -- Licensed to Pwn

Presented by

Patrick Gray
Patrick Gray

CEO and Publisher

Adam Boileau
Adam Boileau

Technology Editor

On this week’s show Patrick Gray and Adam Boileau discuss recent security news, including:

  • Apple 0day has everyone freaking out
  • So much more 0day in the wild
  • American Project Raven staffers settle with DoJ
  • Two absolutely bonkers Azure security problems
  • SEC tells corporate America to spill on breaches
  • Much, much more

In this week’s sponsor interview Gigamon’s security product manager Fayyaz Rajpari will be along to talk about some of the work they’ve been doing to integrate their NDR product with Crowdstrike.

Risky Business #638 -- Licensed to Pwn
0:00 / 62:58

Snake Oilers: Get Signal Sciences in your CDN, automate canary generation and cloud your SIEM!

Presented by

Patrick Gray
Patrick Gray

CEO and Publisher

Snake Oilers: Get Signal Sciences in your CDN, automate canary generation and cloud your SIEM! Three solid pitches in this edition…

In this edition of the Snake Oilers we’ll hear pitches from three vendors:

  • Brian Joe from Fastly talks about its integration of the Signal Sciences WAF into its CDN
  • Ben Whitham and Dan Holman talk about HoneyTrace, a canary creation and monitoring automation play
  • Anton Chuvakin from Google Cloud talks about cloud native SIEMs

Links to everything we talked about are in the show notes.

Snake Oilers: Get Signal Sciences in your CDN, automate canary generation and cloud your SIEM!
0:00 / 36:20

Risky Business #637 -- Infosec's bigfoot

Presented by

Patrick Gray
Patrick Gray

CEO and Publisher

Adam Boileau
Adam Boileau

Technology Editor

On this week’s show Patrick Gray and Adam Boileau discuss recent security news, including:

  • Apple backs down on CSAM measures
  • FTC shuts down spouseware company
  • REvil is back!
  • Confluence boxes are getting owned a lot
  • Trickbot crew member arrested in South Korea
  • The Juniper/NSA backdoor story just keeps on truckin’

This week’s show is brought to you by Thinkst Canary. Thinkst’s Jacob Torrey is this week’s sponsor guest. He pops by to tell us about the relaunch of Thinkstscapes, a fantastic quarterly publication that analyses security research.

(Editor’s note: Dmitri Alperovitch is a guest in this podcast and wishes to express his gratitude to Matthew Green of Johns Hopkins University for helping guide him on the Juniper story.)

Risky Business #637 -- Infosec's bigfoot
0:00 / 64:08

Risky Business #636 -- Victims are shunning data extortion payments

Presented by

Patrick Gray
Patrick Gray

CEO and Publisher

Adam Boileau
Adam Boileau

Technology Editor

On this week’s show Patrick Gray and Adam Boileau discuss recent security news, including:

  • More info on the Belarusian Cyber Patriots
  • How infosec overhyped election security risks
  • Is data ransoming dying?
  • All about the Azure Cosmos DB drama
  • Much, much more…

In this week’s sponsor interview Airlock Digital’s Daniel Schell and David Cottingham join the show to talk about EDR bypasses. They are a thing.

Risky Business #636 -- Victims are shunning data extortion payments
0:00 / 65:10

Risky Biz Soap Box: Bad incentives make Microsoft a villain again

Presented by

Patrick Gray
Patrick Gray

CEO and Publisher

In this edition of the Soap Box podcast we’ll be hearing from Ryan Kalember, the EVP of cybersecurity strategy at Proofpoint, a company best known for being an email filtering giant.

Proofpoint’s biggest challenger in that space is Microsoft, and if you’ve been paying attention you’d know that Microsoft is doing an absolutely massive push into the security space. It claims security is a $10bn revenue centre for the company, which is a bit of a screwy situation given a lot of the insecurity its security products mitigate is introduced through deficiencies in its core products.

And, largely, that’s what this interview is about – the screwy incentives that are driving Microsoft’s decisionmaking. More emphasis on security product development, and less effort on securing its core products.

Of course it’s self-serving for Ryan and Proofpoint to give Microsoft a kicking, given Redmond is its primary competitor. But the thing is, Ryan makes some very good points.

We talk about the incentives thing, and then we talk about why active directory is a trashfire and why the replication of the domain trust model in AzureAD is going to eventually bite us all in the ass. The circle of life, enterprise computing fail edition. Enjoy.

Risky Biz Soap Box: Bad incentives make Microsoft a villain again
0:00 / 36:12

Risky Business #635 -- Owned via telnet? Must be "highly sophisticated attackers"!

Presented by

Patrick Gray
Patrick Gray

CEO and Publisher

Adam Boileau
Adam Boileau

Technology Editor

On this week’s show Patrick Gray and Adam Boileau discuss recent security news, including:

  • T-Mobile owned hard
  • USA no fly list winds up on unsecured ElasticSearch in Bahrain… because reasons
  • Facebook scrambles to secure Afghani accounts
  • Hacker steals and returns $600 from de-fi platform
  • Healthcare sector struggles with ransomware attacks
  • A very sweet TCP-based amplification technique that will be A Problem
  • Much, much more

Evan Sultanik and Dan Guido will be joining us to talk about Fickling – a tool developed by Trail of Bits to do unnatural things to the Python Pickle files that are heavily used as a means to share machine learning models. The machine learning supply chain is really quite wobbly, and they’ll be joining us later to talk about that.

Risky Business #635 -- Owned via telnet? Must be "highly sophisticated attackers"!
0:00 / 67:52

Risky Biz Soap Box: HD Moore talks Rumble and DCE/RPC party tricks

Presented by

Patrick Gray
Patrick Gray

CEO and Publisher

I am stoked to be publishing this interview. This Soap Box is brought to you by Rumble, the asset discovery company founded by HD Moore. For those of you who don’t know, HD is a security legend, having done all sorts of amazing research over the years and creating Metasploit all the way back in 2003.

This guy, as you’ll hear, vibrates at a slightly higher frequency than the rest of us. He’s one of those people who’s not only insanely talented, but he’s also insanely hardworking, which is why we get to have nice things like Metsaploit and, now, Rumble.

So: What is Rumble? It’s is an active asset discovery tool. You set it loose on your network and it shows you what’s there… but this isn’t your grandma’s portscanner. This thing can see through walls and around corners, and what it finds will genuinely blow you away. A couple of weeks ago a guy by the name of Tom Lawrence did an awesome 15 minute demo of Rumble for his YouTube channel.

I would highly recommend you watch it, even before you listen to this podcast. He does a fantastic job of demoing the product and showing that it’s able to make sense of what it sees to a very surprising degree. Tom demos it on a small network, but yeah, it scales – HD says Rumble counts a Fortune 5 among its customers.

Anyway, what HD has done with Rumble is create a tool – a lightweight scanner you can run from basically anywhere in a network – that will show you networks you didn’t know existed, it’ll identify devices with ridiculous granularity… it can even tell you if a windows box has EDR on it or a wireless card installed, all with an unauthenticated network scan.

Risky Biz Soap Box: HD Moore talks Rumble and DCE/RPC party tricks
0:00 / 35:34