HeyJaredSysAdmin Weekly
Welcome to the SysAdmin Weekly Podcast, your go-to source for IT-related content tailored to busy system administrators in the trenches.
- Indexed episodes, last 90 days
- 11
- Latest publication
- Sep 27, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 3, 2026
Latest episodes
061 - Why Does IT Burn People Out? SysAdmin Mental Health with Paul Croker (opens the original)
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We throw an alert when a disk hits 85 percent. Nobody has ever built the monitoring system for the person who gets the alert. Andy Syrewicze is joined by Paul Croker, a UK IT pro who founded 404 Stress Not Found, a nonprofit built because tech and cyber people had nowhere safe to talk about burnout. Paul walks through the perfect storm that put him on a Berlin stage telling his own story, and Andy gets into the MSP years that surfaced a generalized anxiety disorder. They get specific about hero
060 - Microsoft 365 Licensing in 2026: What Changed and What It Costs You (opens the original)
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Microsoft has no intention of making 365 licensing simpler, because the complexity is what gives them room to negotiate. Andy Syrewicze gets Paul Schnackenburg back on the show to map Microsoft 365 licensing as it actually stands in 2026. The July price increases and the one SKU that did not move, the Defender and Purview add-ons that let a 300 seat shop buy E5 capability without buying E5, the features that left E5 for the Entra Suite, and E7 at $99 per user per month with Agent 365 attached. P
059 - How Should SysAdmins Handle Remote Access in 2026? (opens the original)
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Which protocol you use to reach the box is the least interesting decision you will make about remote access. Andy Syrewicze and Eric Siron go after the piece they cut from the tools episode. Eric lands the sharpest version half an hour in: what you are actually doing is moving from one-sided authentication to mutual authentication. Around that sit overlay networks against the VPN concentrator, the RMM console as the most attractive target in an MSP estate, the outbound tunnel nobody watches for,
058 - What Tools Do SysAdmins Actually Use Every Day? (opens the original)
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The tools that stay in the kit for a decade are the ones that still work when the network, the domain, or the boot volume is the thing that broke. Andy Syrewicze and Eric Siron open their real toolboxes and argue about what earns permanent residency. nmap and Wireshark for what is actually on the wire, Sysinternals for what a box is really doing, GParted and SystemRescue for the volume that will not mount, and the chkdsk, DISM, then SFC sequence Eric can run in his sleep. Andy's list skews hard
057 - Is Your Air Gap Actually an Air Gap? Port 22 Says No (opens the original)
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Somewhere inside that isolated network, port 22 is open, and it has been open since the outage six months ago that nobody wrote up. Andy Syrewicze and Eric Siron take apart a term the industry uses constantly and almost never earns. They walk the management plane hole by hole: SSH and RDP so somebody can patch the thing, SMB for the files that have to move, DNS and NTP because nothing works without them, and the iDRAC, iLO, and IPMI boards that get parked on the management VLAN and then never pa
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