The 404 Media Podcast – "This Podcast Will Hack You"

Date: December 3, 2025
Hosts: Joseph, Sam (with guest Matthew Gault in segment two)

Overview

This episode features two major investigative tech stories tackled by the 404 Media team. Joseph and Sam dive into a strange cyber mystery involving Apple Podcasts being used in potential hacking attempts, while Matthew Gault joins later to discuss the ethical chaos of war betting—specifically, how a popular frontline map of Ukraine was suspiciously edited in sync with a large bet on the prediction market Polymarket. The episode is packed with technical insights, ethical debates, and the team’s signature mix of humor and deep reporting.

1. Strange Hack: Inexplicable Activity on Apple Podcasts

Discussed by: Joseph & Sam
Main Segment: 00:59 – 21:40

Summary

• Background:
  Joseph notices bizarre behavior on his Mac: his Apple Podcasts app opens randomly, displaying obscure or sketchy podcasts with titles ranging from script-like gibberish to Arabic phrases, and sometimes containing coded links and references to weird religious content.

  • Joseph: “I will go and unlock my Mac… The podcast app will have opened by itself and it will be displaying some random ass spirituality app, education app, religion as well.” (03:13)

• What’s Weird?:

  • The podcasts are not ones Joseph subscribes to and have odd titles; sometimes the titles appear to contain scripts or direct links.
  • Examples include podcast titles like “5xew e2 single quote, double quote, ampersand hash x22… on click alert…” and suspicious URLs.
  • Some shows linked directly to Play Store URLs or contained Gmail addresses.

• Scarier Possibilities Considered:
  Joseph feared it might be targeted hacking or device compromise, especially given his background as a security journalist.

  • “My first reaction was concern, worry… is this something that’s really, really bad?” (02:59)

• Realization:
  Some podcasts played legitimate (though irrelevant) content, like sermons; others were just silence. All podcasts unearthed were several years old, suggesting possible hijacking or exploitation rather than legitimate recommendations.

  • “They’ve clearly been co-opted in some way or some shenanigans are going on…” (08:00)

• Technical Analysis:
  One podcast had a title resembling a cross-site scripting (XSS) attack—a classic web exploit where scripts can run in a user’s browser. This potentially enables malicious payload delivery if exploited further.

  • Joseph: “It appeared to be a cross site scripting attack… a low hanging fruit attack... It was basically what script kiddies were doing…” (10:10)

Expert Input – Patrick Wardle

Timestamps: 14:02 – 17:19

• Joseph consulted Mac security expert Patrick Wardle, who was intrigued and recreated the suspicious behavior by crafting a site that auto-opened podcasts on Joseph’s machine without any prompts.
  • “He did a proof of concept where he sent me a link… it automatically opened the 404 Media Podcast on my device without a pop up… just automatically opens straight on the podcast." (16:16)
• Wardle highlighted the risk: While this isn’t an attack by itself, it could be a vector for serious attacks IF a vulnerability in Apple Podcasts is found.
  • "[Wardle] said... this is not an attack, but it does create a very effective delivery mechanism if... a vulnerability exists in the podcast's app." (16:52)

Apple’s Response?

• Joseph sent five emails and direct contacts to Apple, which acknowledged receipt only for unrelated topics but never responded to concerns about the podcast issue.
  • “Apple did not acknowledge or respond to five emails… The company did respond to other emails for different articles I was working on across that time…” (20:18)

Broader Context

• The spammy and potentially threatening podcast hijackings resemble other platform manipulation tricks (like Google Calendar spam), revealing ongoing weaknesses in how large platforms handle user-generated content and exploit possibilities.
  • “This podcast stuff is similar to that vibe... but it's not super alarming. That said, if you could deliver... malware to somebody... through a native pre installed... official Apple [app]. That's pretty bad.” (19:06)

Memorable Quotes

• Joseph on user confusion:
  “I’m like the Simpsons Smithers gif surrounded by women, but it’s that but with podcasts basically. It’s horrible.” (08:00)
• Sam on skepticism and humor:
  “Free Will, Free Will, that’s a great one. I’m a big fan, I’m a top listener of Free Will, Free Will…” (08:01)

2. Betting on War: Polymarket, Maps, and a Shady Edit

With Matthew Gault
Main Segment: 24:40 – 38:58

Background: What Is Polymarket?

• Polymarket is a “predictive betting market” where users wager on outcomes of real-world events—elections, wars, financial decisions, etc. It’s positioned by founders as “the future of news,” using market sentiment as “truth.”
  • Matthew: “It basically allows you to gamble on everything, including the outcomes of individual battles in a war zone.” (25:48)
• The rationalization: A person’s willingness to risk money supposedly reflects their truest expectations about reality.

Tying It to Ukraine

• Bets placed on whether specific Ukrainian towns (such as Myrhorod in Donetsk) would fall to Russia by a certain date.
• ISW (Institute for the Study of War) produces a widely-accepted map used as the basis for settling these bets.

The Incident

Timestamps: 29:23 – 36:59

• A large, unusual bet (over $1M in volume) depended on whether a particular block of the city would be captured by a deadline.
• Around 6:00am on Nov 15, before ISW’s normal update window, the map changes in just the relevant spot, showing the city “captured.” Right after, the map is reverted.
• ISW confirms an “unauthorized edit” was made overnight, later reversed, and publicly distances themselves from the use of their map for betting.
  • Matthew, quoting ISW: “ISW strongly disapproves of such activities and strenuously objects to the use of our maps for such purposes, for which we emphatically do not give consent.” (33:32)
• PolyMarket pays out the bet based on the map snapshot, despite the reversal. No one disputes the outcome through PolyMarket’s odd blockchain-based dispute process.
  • Matthew: “Nobody disputed anything... The money was paid out and the ISW map reverted after that.” (36:47)

Analysis & Ethics Debate

• Possibilities:
  • Someone with access, or a hacker, manipulated the map to ensure the bet’s specific outcome.
  • PolyMarket’s systems, dependent on snapshot, allow for such fraudulent manipulation unless manually disputed.
  • The process for challenging bad resolutions is convoluted and rarely used, leaving room for abuse.
• Ethical Concerns:
  • Both team and audience express profound discomfort with the idea of gambling on real-world death and tragedy.
  • Matthew: “I think it’s a moral state on your soul if you do it full stop. Sorry if you’re betting on the outcome of a conflict like this.” (38:17)
  • Sam: “So cynical. It’s such a cynical...” (38:25)
  • Matthew: “War is a horrifying thing where people die...and people are, like, laying bets on it... That’s awful. It is a bad thing to do and you should not do it.” (38:29)

3. Notable Quotes & Moments

On the Apple Podcasts Exploit

• Joseph: “He sent me a link... it automatically opened the 404 Media Podcast on my device without a pop up... Which he found pretty interesting.” (16:16)

On Betting on War

• Matthew: “ISW strongly disapproves of such activities and strenuously objects to the use of our maps for such purposes, for which we emphatically do not give consent.” (33:32)
• Matthew, on ethics: “I think it’s a moral state on your soul if you do it full stop. Sorry if you’re betting on the outcome of a conflict like this.” (38:17)
• Matthew, bluntly: “War is a horrifying thing where people die... and people are, like, laying bets on it... That’s awful.” (38:29)

4. Key Timestamps for Important Segments

• Apple Podcasts ‘Hack’ Discovery: 01:56 – 21:40
• Break, Ads (skipped)
• War Betting & Map Exploitation: 24:40 – 38:58
• Ethics Discussion: 38:17 – 38:58

5. Conclusion & Tone

The episode blends investigative rigor with sharp, sometimes irreverent commentary. The team effectively demystifies two complex stories: one technical (the Apple Podcasts opening exploit), and the other an ethical minefield (war betting systems being gamed). Through experts and transparent self-examination, 404 Media continues their mission of exposing the strange, dark corners of technology—always with a critical, human-centered approach.

For further information and extra episodes, 404 Media encourages listeners to subscribe via 404media.co.

Summary prepared by Podcast Summarizer
(Content drawn closely from original transcript; all quotes and ideas directly attributed to hosts and guests as indicated.)