Best Rory Monaghan Podcasts (2025)

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From Packaging Apps to Podcasting with Rory Monaghan 53:04

Play Pause

8d ago53:04

53:04

Rory Monaghan shares his extensive journey in the IT field, starting from his early days in application packaging to his current role in end user computing. He discusses the evolution of application virtualization, particularly App-V, and its impact on organizations. Rory emphasizes the importance of community through user groups and the value of p…

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Helpdesk Scars & PowerShell Wins with Andrew Taylor 55:52

1d ago55:52

55:52

Andrew Taylor shares his journey from studying business to becoming a seasoned IT professional with over 20 years of experience. He discusses his early days in help desk support, his transition to end user computing, and the challenges he faced in various IT roles, including managing multiple tenants in the MSP world. Andrew emphasizes the importan…

1
UAC Prompt Issue More Widespread Than Thought! Patch Tuesday News! Azure Disruption in Middle East! 28:31

18h ago28:31

28:31

On this episode, I cover the Windows Updates for September's Patch Tuesday, an ongoing issue from August's Windows Updates, legal shenanigans impacting enterprise IT and consumer tech and much more!Reference Links: https://www.rorymon.com/blog/uac-prompt-issue-more-widespread-than-thought-patch-tuesday-news-azure-disruption-in-middle-east/…

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Writing, Teaching, and Defending: Ru Campbell’s IT Adventures 58:00

21h ago58:00

58:00

Ru Campbell shares his journey from starting in IT in 2012 to becoming a Microsoft 365 consultant and security expert. He discusses the importance of help desk experience, betting on oneself in career progression, and the transition to specializing in Microsoft Defender. Ru emphasizes the value of understanding security practices, the challenges of…

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Windows 11 25H2 Now In Preview! Citrix NetScaler Vulnerabilities Disclosed! Amazing AI Stethoscope! 18:55

8d ago18:55

18:55

I cover the announcement of Windows 11 25H2 entering preview, worrying details about Citrix Netscaler vulnerabilities, a company changing AI approach after public failures and much more!Reference Links:https://www.rorymon.com/blog/windows-11-25h2-now-in-preview-citrix-netscaler-vulnerabilities-disclosed-amazing-ai-stethoscope/…

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Windows Update Woes! xAI Brings Suit Against Apple and OpenAI! Is GenAI a Bubble?! 25:49

18d ago25:49

25:49

On this episode, I cover problems caused by recent Windows Updates, Gartner's update to the DaaS Magic Quadrant, Windows 10 ESU concerns and much more!Reference Links:https://www.rorymon.com/blog/windows-update-woes-xai-brings-suit-against-apple-and-openai-is-genai-a-bubble/By Rory Monaghan

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Building Better Reporting with Garth Jones 1:08:14

15d ago1:08:14

1:08:14

Garth Jones shares his extensive journey in the IT field, starting from his early days running a BBS to becoming a pivotal figure in endpoint management with SMS. He discusses the evolution of IT roles, the importance of proactive management, and the challenges he faced while building Enhansoft. Garth also reflects on his experiences with blogging,…

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Networking, Fundamentals, and the Future of IT with Mattias Melkersen 47:10

21d ago47:10

47:10

In this conversation, Mattias Melkersen shares his journey from dropping out of school to becoming a successful IT consultant. He discusses the importance of mentorship, continuous learning, and the impact of AI on IT management. Mattias emphasizes the need for networking and community building in the IT field, as well as the significance of unders…

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Windows 12 Predictions! Patch Tuesday News! Teams Security Enhancements! 17:09

23d ago17:09

17:09

On this episode, I cover the news from Patch Tuesday including an update issue on Windows 11 when using WSUS, I get into a new SSO feature for macOS and much more!Reference Links:https://www.rorymon.com/blog/windows-12-predictions-patch-tuesday-news-teams-security-enhancements/By Rory Monaghan

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GPT-5 Has Arrived! Win365 Reserve in Preview! Lawsuit to try to Extend Windows 10 Support! 21:46

1M ago21:46

21:46

On this episode, I cover the lackluster launch of GPT-5, a new preview of a Windows 365 Reserve feature, several vulnerability exploits and much more!Reference Links:https://www.rorymon.com/blog/gpt-5-has-arrived-win365-reserve-in-preview-lawsuit-to-try-to-extend-windows-10-support/By Rory Monaghan

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Pedaling Through IT Careers with Paul Winstanley 1:02:44

1M ago1:02:44

1:02:44

In this conversation, Paul Winstanley shares his journey in the IT industry, starting from his early days in retail IT support to specializing in endpoint management and becoming a community leader through blogging and speaking engagements. He discusses the importance of mentorship, the evolution of his career into consulting, and the impact of AI …

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From Dismantling a PC at 14 to Co-Founding a Tech Company with Jose Schenardie 1:07:03

1M ago1:07:03

1:07:03

In this conversation, Jose Schenardie shares his journey from starting his IT career in Brazil to becoming a co-founder of a cybersecurity company in Australia. He discusses the importance of niche conferences like MMS, the evolution of endpoint management with Intune and SCCM, and the role of AI in shaping the future of IT. Jose emphasizes the val…

1
Urgent Exchange Security Advisory! Critical Adobe Vulnerability! Nvidia Extending Win10 Support! 26:58

1M ago26:58

26:58

On this episode, I cover a critical Adobe vulnerability that gets a 10 on the severity scale, recent year on year metrics from AWS and much more!Reference Links:https://www.rorymon.com/blog/urgent-exchange-security-advisory-critical-adobe-vulnerability-nvidia-extending-win10-support/By Rory Monaghan

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Flights Cancelled After Cyber Attack! ChatGPT Study Mode! UK Age Verification! 22:36

2M ago22:36

22:36

On this episode, I cover a story about an airline grounding flights after a cyber attack, a macOS security concern, application containers for Windows on Arm, a whole lot of AI news and more!Reference Links:https://www.rorymon.com/blog/flights-cancelled-after-cyber-attack-chatgpt-study-mode-uk-age-verification/…

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Cloud Skills, Content Creation & Cardio – Andy Jones IT Journey 1:01:02

2M ago1:01:02

1:01:02

In this conversation, Andy Jones shares his extensive journey in the IT field, starting from his early days in web development to his current role focusing on cloud technologies and Intune. He discusses the importance of continuous learning, mentorship, and the evolution of technology, particularly AI and its implications for IT professionals. Andy…

1
Major SharePoint Attack Underway! Connect Cache Goes GA! New AI Feature in Win11! 25:18

2M ago25:18

25:18

On this episode, I cover the active exploitation of a critical SharePoint vulnerability, a Windows Server update causing cluster issues, the Citrix Bleed 2 exploit, and Google’s discovery of a SonicWall backdoor and more.Reference Links:https://www.rorymon.com/blog/major-sharepoint-attack-underway-connect-cache-goes-ga-new-ai-feature-in-win11/…

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Helpdesk to Consulting with Chris Cavazos on Shaping Tech Careers 51:19

2M ago51:19

51:19

In this conversation, Chris Cavazos shares his journey in the IT field, starting from his early experiences in the 90s to his current role as a principal consultant. He discusses the importance of mentorship, the transition from in-house IT to consulting, and the impact of Azure Virtual Desktop during the pandemic. Chris also touches on his persona…

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Google AI Security Milestone! In-box Windows Apps to be Updated! Issues Caused by Updates! 21:33

2M ago21:33

21:33

I cover some issues caused by the latest Windows Updates, give an update on the M&S cyber attack, I discuss a landmark for Google's AI security platform and much more!Reference Links:https://www.rorymon.com/blog/google-ai-security-milestone-in-box-windows-apps-to-be-updated-issues-caused-by-updates/By Rory Monaghan

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From Construction Sites to Configuration Profiles with Jóhannes Geir Kristjánsson 55:41

2M ago55:41

55:41

Johannes Geir Kristiansson shares his unique journey from a construction background to a successful career in IT, particularly in endpoint management and Intune. He discusses the challenges and rewards of transitioning from a hands-on trade to a more abstract field, emphasizing the importance of community and knowledge sharing. Johannes also reflec…

1
Windows Update Causing Firewall Error! Patch Tuesday News! Grok Goes Crazy! 19:15

2M ago19:15

19:15

I cover the latest Patch Tuesday news, more metrics on Windows 11 adoption, some InfoSec stories and much more!Reference Links:https://www.rorymon.com/blog/windows-update-causing-firewall-error-patch-tuesday-news-grok-goes-crazy/By Rory Monaghan

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How Dustin Gullett Went from Mowing Lawns to Microsoft MVP 56:30

2M ago56:30

56:30

Dustin Gullit shares his journey from mowing lawns for a school district to becoming an IT consultant with a wealth of experience in military network security, healthcare IT, and MDM solutions. He discusses the evolution of Intune, the impact of AI on technology and daily life, and his passion for photography and blogging. Dustin emphasizes the imp…

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Win10 Lingers On! Windows Update Delay Issue! Facial Recognition Could Become the Norm! 23:46

2M ago23:46

23:46

On this episode, I go over several updates on Windows 10 end of support and the state of the union regarding Windows 11 adoption, I also give an update on CitrixBleed2, HPE's attempted acquisition of Juniper and much more!Reference Links:https://www.rorymon.com/blog/win10-still-on-half-of-business-devices-windows-update-delay-issue-facial-recogniti…

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How Nearly Becoming a Doctor Led to a Career in Cyber Security with Spencer Alessi 53:23

3M ago53:23

53:23

Spencer Alessi shares his journey from almost becoming a doctor to pivoting to IT, emphasizing the importance of help desk experience, mentorship, and continuous learning. He discusses his passion for systems administration, the significance of disaster recovery testing, and his transition into security. Spencer also reflects on his experiences in …

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Free Windows 10 ESU Offer! Known OneDrive Issues! Changes for Windows 365! 21:59

3M ago21:59

21:59

I cover another issue related to the June Windows Updates, some known issues facing OneDrive customers, announcements from Cisco Live 2025 and HPE Discover plus more!Reference Links:https://www.rorymon.com/blog/free-windows-10-esu-offer-known-onedrive-issues-changes-for-windows-365/By Rory Monaghan

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Naming OUs and Racing Bikes: The Balanced Life of Michael Escamilla 56:32

3M ago56:32

56:32

Michael Escamilla shares his journey in the IT field, discussing his experiences at conferences, his involvement with OSD Cloud, and the importance of community engagement. He reflects on his career path, the challenges faced in IT, and the significance of automation. Michael emphasizes the need for continuous learning and offers advice for aspirin…

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Imposter Syndrome, Authorship, and Entrepreneurship with David Brook 57:09

3M ago57:09

57:09

David Brook shares his journey in the IT field, discussing his early experiences, the importance of apprenticeships, and the challenges of starting his own business. He emphasizes the value of community, public speaking, and the need for continuous learning in the fast-paced world of technology. David also opens up about his struggles with imposter…

1
Microsoft 365 Authentication Issues! Danish Agency to Ditch Office! June Update Issue! 12:28

3M ago12:28

12:28

On this episode, I provide an update on the recent Windows updates and report of an issue caused by one of the updates. I cover some new enhancements from OpenAI, the culmination of a 4 year study into remote work and more!Reference Links:https://www.rorymon.com/blog/microsoft-365-authentication-issues-danish-agency-to-ditch-office-june-update-issu…

1
Apple Announcements from WWDC! Patch Tuesday News! Grim Job Forecast for IT Pros! 23:19

3M ago23:19

23:19

On this episode, I talk about a worrying job forecast for IT Pros, several consumer side announcements from Apple and Microsoft, Patch Tuesday news and much more!Reference Links:https://www.rorymon.com/blog/apple-announcements-from-wwdc-patch-tuesday-news-grim-job-forecast-for-it-pros/By Rory Monaghan

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From Paramedic to Redmond, Sean Bulger’s tech journey 1:12:07

3M ago1:12:07

1:12:07

In this conversation, Sean Bulger shares his journey through the IT landscape, discussing his experiences as a consultant, the importance of a growth mindset, and the value of mentorship. He reflects on his diverse career path, that included jobs as a plumber and paramedic, and emphasizes the significance of community engagement and continuous lear…

1
Login VSI Announces an Acquisition! IGEL Announces an Acquisition! New Rules Set for USB-C! 23:44

3M ago23:44

23:44

On this episode, I talk about another issue caused by the May Windows Updates, some exciting announcements around acquisitions in EUC and much more!Reference Links:https://www.rorymon.com/blog/login-vsi-announces-an-acquisition-igel-announces-an-acquisition-new-rules-set-for-usb-c/By Rory Monaghan

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Steve Weiner’s Unexpected Tech Journey: Music, Youtube, and Modern Management 59:22

4M ago59:22

59:22

In this engaging conversation, Steve Weiner, co-founder of Get Rubix, shares his unique journey from a music career to the tech industry, detailing his experiences at Apple and as a tech consultant. He discusses the evolution of his YouTube channel, the impact of pandemic on IT practices, and the importance of community engagement through open-sour…

1
Google I/O Announcements! Resume In-App Option Coming! AV in Image Management Tip! 38:55

4M ago38:55

38:55

On this episode, I cover a lot more AI news (no surprise), an update on the Coinbase breach, a fix for the Bitlocker recovery prompt issue on Windows 10 and more!Reference Links:https://www.rorymon.com/blog/google-i-o-announcements-resume-in-app-option-coming-av-in-image-management-tip/By Rory Monaghan

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Code, Cloud & Confidence with Hailey Phillips 1:06:47

4M ago1:06:47

1:06:47

In this episode, Hailey Phillips shares her journey from an HR internship to becoming a prominent figure in the IT industry. She discusses her passion for technology, the importance of automation and cloud computing, and the role of soft skills in tech. Hailey also reflects on her experiences in the gaming industry, her travels to Japan, and the si…

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Microsoft BUILD 2025 Highlights! Update Causing Bitlocker Prompts! OpenAI Announces New Agent! 32:29

4M ago32:29

32:29

On this episode, I cover some of the fallout from the recent Windows Updates, I get into some highlights from Microsoft BUILD and much more!Reference Links:https://www.rorymon.com/blog/microsoft-build-2025-highlights-update-causing-bitlocker-prompts-openai-announces-new-agent/By Rory Monaghan

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Steve Jesok’s Journey - From Rockstar to IT Rockstar 53:25

4M ago53:25

53:25

In this conversation, Steve Jesok shares his journey into the IT field, his involvement with user groups, and the evolution of community engagement in technology. He reflects on his early career, transitioning from a professional musician to an IT professional, and highlights the importance of user groups as resources for learning and networking. 0…

1
Spectre v2 Raises its Ugly Head Once More! Patch Tuesday News! Microsoft Announces Layoffs! 23:29

4M ago23:29

23:29

On this episode, I cover the details of the latest Windows Updates for this month's Patch Tuesday, I dive into the latest AI news, an Office bug causing high resource utilization and much more!Reference Links:https://www.rorymon.com/blog/spectre-v2-raises-its-ugly-head-once-more-patch-tuesday-news-microsoft-announces-layoffs/…

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Dean Ellerby on IT, AI, and Launching His YouTube Journey 58:16

4M ago58:16

58:16

In this engaging conversation with Dean Ellerby, he shares his journey through the tech industry, starting from his early experiences in a gaming company to becoming a consultant specializing in SCCM and Intune. He discusses the challenges and learning moments throughout his career, including his transition to content creation on YouTube during the…

1
Apple Smacked Down in Court! Good Quarter for Microsoft! Discount for New Win365 Customers! 18:51

4M ago18:51

18:51

On this episode, I cover the details of the latest court ruling against Apple on its alleged anti-competitive practices. I also dive into newly disclosed cyber attacks in the UK and much more!Reference Links:https://www.rorymon.com/blog/apple-dressed-down-in-court-microsoft-beats-expectations-significant-win365-discount/…

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Community, AI, and the Future of IT with Mike Terrill 56:18

5M ago56:18

56:18

Fabian and Mike Terrill discuss a variety of topics ranging from the extreme weather in Phoenix to the intricacies of community engagement through user groups like azsmug. They delve into the challenges faced by user groups post-COVID, the evolution of systems management, and the future of device management in the context of AI. Mike shares valuabl…

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From Portraits to PowerShell: David Segura on Building OSDCloud 47:50

5M ago47:50

47:50

In this conversation, David Segura discusses the birth of OSDCloud, highlighting its popularity and the significant impact of automation in IT management. He also touches on future trends in system administration, emphasizing the importance of adapting to new technologies and I learn how down to earth he is! Chapters 00:00 Introduction to David Seg…

1
Bryan Dam – Onesies, Sysadmin Life & Sneakernet Solutions 1:11:21

5M ago1:11:21

1:11:21

In this conversation, Bryan discusses his early experiences in IT management, particularly focusing on the unconventional methods he employed, such as the 'sneaker net' approach, to manage devices and install software. He reflects on the challenges and best practices he learned along the way. Chapters 00:00 Introduction and Background 03:47 Career …

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Matt Zaske’s Mustache Origin + Task Sequences in 2025 1:14:19

5M ago1:14:19

1:14:19

Matt Zaske, a seasoned sysadmin in higher ed, dives into device management, Windows 11 migration, and how his theater background shapes his IT communication. He shares his path into tech speaking, explores home automation, and showcases his passion for 3D printing and custom conference collectibles. We also learn the fun origin story of his iconic …

1
Many Suitors After Google Chrome! M&S Hit by Ransomware! Hotpatching to Require Subscription! 16:13

5M ago16:13

16:13

On this episode, I cover some recent issues caused by the April Windows Updates, I cover the news of many suitors vying for Google Chrome, annoyances with ChatGPT and more!Reference Links:https://www.rorymon.com/blog/many-suitors-after-google-chrome-ms-hit-by-ransomware-hotpatching-to-require-subscription/…

1
Entra ID Account Lockouts! Critical PyTorch Bug! Scheduled Tasks for Gemini! 18:50

5M ago18:50

18:50

I cover the news over the weekend about Entra ID account lockouts, I discuss several recent vulnerabilities, a policy change by Google and more!Reference Links:https://www.rorymon.com/blog/entra-id-account-lockouts-critical-pytorch-bug-scheduled-tasks-for-gemini/By Rory Monaghan

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April Updates Causing Headaches! Google Announces Layoffs! Return of a Free ESXi! 18:04

5M ago18:04

18:04

In this episode, I cover news of fallout from the April Windows updates, the latest AI developments, a new FSLogix release and more.Reference Links:https://www.rorymon.com/blog/april-updates-causing-headaches-google-announces-layoffs-return-of-a-free-esxi/By Rory Monaghan

1
Confusing Patch Tuesday News! Cyber Gang's Messages Leaked! WSUS Driver Sync Revived! 34:15

5M ago34:15

34:15

In this episode, I provide a roundup of Patch Tuesday news including worrying aspects of one patch and vulnerability mitigation process, I also provide an update on the Oracle breach, a change to Windows 11 Start Menu and more!Reference Links:https://www.rorymon.com/blog/confusing-patch-tuesday-news-cyber-gangs-messages-leaked-wsus-driver-sync-revi…

1
Major Data Breach of Popular EHR Platform! New Win11 Roadmap! VMware Suing Customer! 29:09

5M ago29:09

29:09

I cover the concerning story of a data breach of Oracle Health and a haphazard disclosure by Oracle, I also cover multiple AI related stories (of course), provide updates on some Windows issues caused by recent updates and much more!Reference Links:https://www.rorymon.com/blog/major-data-breach-of-popular-ehr-platform-new-win11-roadmap-vmware-suing…

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Cloudflare Launches AI Tricking Feature! Google Drive Arm Compatibility! OneNote App Support to End! 24:29

6M ago24:29

24:29

I provide an update on the recent GitHub Actions exploits, information on a recently disclosed vulnerability in Veeam's backup service, the end of support for a OneNote app and much more!Reference Links:https://www.rorymon.com/blog/cloudflare-launches-ai-tricking-feature-google-drive-arm-compatibility-onenote-app-support-to-end/…

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Google's Largest Acquisition Ever! Windows Update Concerns! Java 24 Goes GA! 33:01

6M ago33:01

33:01

In this episode, I cover the announcement of Google's largest ever acquisition, info on issues caused by this month's Windows Updates and much more!Reference Links:https://www.rorymon.com/blog/googles-largest-acquisition-ever-windows-update-concerns-java-24-goes-ga/By Rory Monaghan

1
OneDrive to Prompt Users! Patch Tuesday News! Remote Desktop App Being Retired Soon! 37:36

6M ago37:36

37:36

In this episode, I cover the latest in AI news, the removal of a recent Windows 11 upgrade block for AutoCAD customers, an incredible polymorphic extension exploit in Chrome plus more!Reference Links:https://www.rorymon.com/blog/onedrive-to-prompt-users-patch-tuesday-news-remote-desktop-app-being-retired-soon/…