Technical Debt Collector
When O discovers a three-year-old temp admin account still running in production, Cyrus points out the real problem.
View episode →A series from O-Cyrus
The Adventures of O & Cyrus
Ship vs secure. O wants to deploy. Cyrus wants to patch. Catch the latest episode.
Hybrid Infrastructure
O pitches cloud migration while Cyrus literally patches the physical server that's been running under his desk for three years.
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The Fastest Path to Compliance
O discovers that giving everyone admin rights is much faster than learning IAM policies, while Cyrus mourns the death of role-based access control.
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Success Alert
O's enthusiasm for monitoring leads to 3am pages celebrating uptime instead of downtime.
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The Friday Deployment Window
O discovers Cyrus has already retreated to his disaster bunker—with the pager conspicuously turned off—right before the big Friday afternoon deploy.
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Global Latency Test
O's enthusiastic 47-region AWS deployment sends the monthly cloud bill into orbit.
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Documentation Best Practices
O's idea of documenting API credentials the night before a compliance audit creates an emergency for Cyrus.
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Defense in Depth
O's service account has 47 automated workarounds for every MFA prompt Cyrus deployed.
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Double Booking
When the maintenance window and the product launch are scheduled for the exact same slot, someone's calendar is about to have a very bad day.
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Drift Happens
Cyrus spent all week building infrastructure as code while O just fixed it with one console click.
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Plan Review
O is ready to apply the Terraform plan while Cyrus notices something alarming in the diff.
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Mutual Attestation
When the auditor asks who owns SOC2 compliance, O and Cyrus simultaneously point at each other.
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Probably Fine
O's relaxed on-call philosophy meets Cyrus's morning inbox of 87 unread alerts.
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The Escalation Ladder
When every user request becomes a climb toward domain admin, O and Cyrus discover the real meaning of privilege escalation.
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Shadow Procurement
The Adventures of O & Cyrus — Marketing's DIY cloud account gives Cyrus an instant stress disorder.
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Sleep-Driven Development
The Adventures of O & Cyrus — O grants admin to everyone at 3pm; Cyrus writes least-privilege policies at 3am.
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Labor Day Deploy
The Adventures of O & Cyrus — O sees an empty office as the perfect deployment window, but Cyrus has other plans.
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Controlled Detonation
The Adventures of O & Cyrus — O clicks the phishing email in production while Cyrus discovers it's happening in real-time.
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The 4:55pm Deploy
The Adventures of O & Cyrus — O discovers that Cyrus has already escaped to his weekend hammock before the Friday afternoon deployment window.
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Staging Fidelity
The Adventures of O & Cyrus — O discovers why their staging environment isn't quite as production-like as everyone thought.
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The Second Factor
The Adventures of O & Cyrus — When the executive asks why they need MFA if they already have a password, Cyrus tries an analogy that backfires spectacularly.
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Critical Severity Morning
The Adventures of O & Cyrus — When your coffee intake scales linearly with the number of CVEs in your inbox.
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Critical Path Analysis
The Adventures of O & Cyrus — When the security audit delivers 47 findings two weeks before launch day, someone's definition of 'critical' needs recalibrating.
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Tabletop Realism
The Adventures of O & Cyrus — When your ransomware tabletop exercise gets a little too immersive.
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The Freeze Frame
The Adventures of O & Cyrus — When your change freeze meets your CI/CD pipeline, someone's going to blink first.
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War Room Capacity
The Adventures of O & Cyrus — When your incident response war room has more stakeholders than the actual incident has affected users.
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The Compliance Checklist
The Adventures of O & Cyrus — When your password policy passes audit but fails reality.
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The Peer Review Bypass
The Adventures of O & Cyrus — When a developer discovers the ancient art of merging your own PR at 4:47 PM on Friday.
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The Demo Gods Are Angry
The Adventures of O & Cyrus — When the VPN goes down five minutes before the board presentation, O discovers Cyrus has been preparing for this moment his entire career.
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