Return-Path: Delivered-To: alvarochf@traceseis.com Received: from cs510.bluehost.com by cs510.bluehost.com with LMTP id QNepOT2992hZjQgAWiBQxw (envelope-from ) for ; Tue, 21 Oct 2025 11:05:01 -0600 Return-path: Envelope-to: alvarochf@traceseis.com Delivery-date: Tue, 21 Oct 2025 11:05:01 -0600 Received: from see.rippling.com ([172.246.46.190]:31284) by cs510.bluehost.com with esmtps (TLS1.3) tls TLS_AES_256_GCM_SHA384 (Exim 4.98.2) (envelope-from ) id 1vBFnB-00000002bt6-1buv for alvarochf@traceseis.com; Tue, 21 Oct 2025 11:05:01 -0600 DKIM-Signature: a=rsa-sha256; bh=AT1Xk82ppS8fwTRMX/lAuVHJbPyhfVAATp4MIBbd5j4=; c=relaxed/relaxed; d=see.rippling.com; h=to:cc:from:reply-to:subject:date:mime-version:content-type:list-id:list-unsubscribe:x-csa-complaints:list-unsubscribe-post:message-id:sender:x-sib-id:x-mailin-client:x-mailin-campaign:feedback-id:bimi-selector; q=dns/txt; s=mail; t=1761066288; v=1; b=WU4qfiLWR7ary9rjzYHpGCz8fL2jm/huJYtOofPpS/umSlinegqVHPR1plvvFDuLyHjoS2H2 a01MmyDyQdE4xqnTp2phgVkLECc7ZjIFBWMURi2PdfUIt2JkCbCyHLoobtxQaw/5C0fqKMfn/Gm SvzHs8n+fIA8dS74JVm5RsKw= To: Subject: =?utf-8?q?=F0=9F=91=8BFarewell_to_Windows_10_+_surviving_compliance_solo?= Content-Type: multipart/alternative; boundary="-------?=_65110-5637466502955" Date: Tue, 21 Oct 2025 17:04:48 +0000 Feedback-ID: 172.246.46.190:6348494_2620:6348494:Sendinblue From: The IT Factor by Rippling List-Id: NjM0ODQ5NC0yNTgyODkzLTEyMzM= List-Unsubscribe: , List-Unsubscribe-Post: List-Unsubscribe=One-Click MIME-Version: 1.0 Message-Id: <202521101704.iu47vwr5aa0csjj@see.rippling.com> Reply-To: X-Csa-Complaints: csa-complaints@eco.de X-Mailer: Sendinblue X-Mailin-Campaign: 2620 X-Mailin-Client: 6348494 X-sib-id: be8ojfC79dSNB8Fh-WygidDwPKMlNyLA_e_jKEbD8drZwvh0bWlPEO_ut1JwZh2ppDMTxmzFZBT98BVHX_4Xn1wMJ0WlT-xSdJGjMciPyf_rbtwKlr3ztoMHrsCVBZx9ZhT-lEEDpb6-tG48VccKh2H6PULPwsBjISmQyslEYOLgX6CF3Ly35_xYRe-eUcvLyZ4-pF0tQvHjLHnhdGWDAtsjiMEO7WZsGy6VGAzn ---------?=_65110-5637466502955 Content-Transfer-Encoding: quoted-printable Content-Type: text/plain; charset=UTF-8 **OCTOBER =C2=A02025** **Matt Lombardo** Editor Can you believe there=E2=80=99s only one more week left in cybersecurity aw= areness month? Me either. Time flies when you=E2=80=99re not getting hacked= .=C2=A0 =F0=9F=AA=A6 So fast, in fact, that the end of the Windows 10 era is alread= y=C2=A0 here.=C2=A0 =F0=9F=93=8B We=E2=80=99ll hear from a team of one who passed five audits = =E2=80=93 both SOC 2 and ISO 27001 =E2=80=93 at Customer.io without a singl= e other team member to back him up. How=E2=80=99d he do it? Scroll down.=C2= =A0 =F0=9F=93=85 And finally, we=E2=80=99ve got a jam-packed lineup of webinars= in the next two weeks, so take a look at what we=E2=80=99ve got on deck an= d register for whichever session you can join. They=E2=80=99re cool, we pro= mise.=C2=A0 =F0=9F=91=8B**We Hardly Knew Ye, Windows 10** ---------------------------------- Say it ain=E2=80=99t so! Microsoft just officially pulled the plug on Windo= ws 10, leaving=C2=A0[over 40% of Windows users](https://gs.statcounter.com/= os-version-market-share/windows/desktop/worldwide/)[=C2=A0](https://gs.stat= counter.com/os-version-market-share/windows/desktop/worldwide/)(!!!) withou= t support. Decisions were made,=C2=A0[as were memes.](https://www.reddit.co= m/r/memes/comments/1o6b6y7/im_not_ready_for_the_win_11_switch/) Many companies will shell out for the year-ish-long lifeline that is Micros= oft=E2=80=99s ESU (Extended Security Updates) program, and that=E2=80=99ll = buy you some time. But now wouldn=E2=80=99t be the worst time to start putt= ing together a plan.=C2=A0 And just in case you missed this =E2=80=93 a lot of people did with all the= noise around Windows 10 =E2=80=93 support also ended for Office 2019 and E= xchange Server 2019 last week, too. And there=E2=80=99s no ESU for those tw= o. It=E2=80=99s an extinction event in Redmond, WA.=C2=A0 So if you=E2=80=99re an all-Microsoft shop, now would be a good time to tak= e some inventory.=C2=A0 **Today**: Discovery time. Pull reports on Windows versions, Office deploym= ents, server OSes, and yes, that SharePoint 2016 instance that the finance = team swears they need. Know your exposure before it knows you. **Tomorrow**: Build retrieval workflows for anything that needs to be tract= or-beamed back to the mothership. Remote employees won't return devices wit= hout automated escalation from gentle reminders to "Hey! CC'd your manager,= thanks for your help.=E2=80=9D=C2=A0 **Next week**: Present the budget bomb. Calculate the costs of replacing wh= at can=E2=80=99t be updated versus the fees you=E2=80=99ll rack up extendin= g support. Throw in the costs of a potential breach, and you=E2=80=99re wel= l on your way to a number that=E2=80=99ll get the C-suite=E2=80=99s sign-of= f. Join us tomorrow for a live webinar relevant to any IT team out there who= =E2=80=99s working with remote users (which, we would venture a guess, is a= lot of you).=20 You=E2=80=99ll hear from a Rippling IT customer at Diana Health, who=E2=80= =99s using the platform to secure ten 24/7 clinic locations, a full telehea= lth operation, and a remote corporate workforce, all while maintaining HIPA= A compliance. [Register now!](https://rippling.registration.goldcast.io/web= inar/9b867911-e70c-49e4-8f59-dc2ce0fa76e0?rtlid=3D00QUd00000QcSfRMAV)=C2=A0 Introducing: **=F0=9F=94=A5=C2=A0**Hotkeys=C2=A0 --------------------------- (I=E2=80=99m working on a logo. Seriously! I am. Stay tuned.)=C2=A0 They=E2=80=99re short videos =E2=80=93 we aim for a minute or less =E2=80= =93 that introduce you to a given feature or use case that Rippling IT can = help you solve. You know, like a keyboard shortcut? Like a hotkey, for inst= ance? I'll see myself out. Today, we=E2=80=99ve got=C2=A0[device policies](https://www.youtube.com/wat= ch?v=3DxG4XgxuEcdw). Because you don=E2=80=99t have to manually configure e= very device for every employee. There's a better way. And while you're at it, want to learn more about all the new features we've= been adding to Rippling? =C2=A0 Join us next Tuesday, 10/28, for The Rippling Rundown, where you=E2=80=99ll= hear from a number of product leaders and Rippling customers on the latest= and greatest in the platform and where we=E2=80=99re headed next. [Registe= r now!](https://rippling.registration.goldcast.io/webinar/80de71b7-b416-466= 6-a89f-71ff13bef88d?rtlid=3D00QUd00000QcSfRMAV) **=F0=9F=93=8B Surviving Solo Compliance at a Growing Startup** ---------------------------------------------------- Three years. Five audits. Zero team members. That's Eldin Scotland's SOC 2 = scorecard at Customer.io, and he's got the battle scars (and clean audit re= ports) to prove it. His first piece of advice may be a comfort to some of you out there. Having= built an IT function at the company from scratch, all by himself, he went = in knowing that it wouldn=E2=80=99t be purely smooth sailing.=C2=A0 =E2=80=9CI knew the work would definitely be daunting at times, definitely = for sure. But I also knew frameworks like SOC 2 and ISO 27001 aren't about = perfection right off the bat. There will be inconsistencies. There will be = missing documentation." In other words, there=E2=80=99s some room to grow into your audit closeup. = And most of his advice has less to do with technical know-how than it does = with learning how to partner across your organization. "Compliance is not just a one-person thing. You need everyone across the en= tire organization to be with you.=E2=80=9D So Eldin built a cross-functional team to get it done: a coalition of the w= illing from engineering, legal, finance, and people ops. They met quarterly= . They created templates together. They owned their pieces. And when the ti= me came, they put them together. "In the event the auditors requested evidence, we already had it. We had al= l of the evidence gathered already." At the end of the day, while Eldin was working as an IT team of one, he mad= e a point of seeking support elsewhere across the org. According to Eldin, = that =E2=80=93 and a seriously impressive slew of automations =E2=80=93 mad= e all the difference.=C2=A0 ** *Facing compliance woes too? Use our=C2=A0**[8-week SOC 2 toolkit](https://= www.rippling.com/resources/soc-2-roadmap-toolkit?rtlid=3D00QUd00000QcSfRMAV= )**=C2=A0to get it all done.=C2=A0* ** *Stay tuned for more advice from today=E2=80=99s IT and security pros every= week. And if you have a question you=E2=80=99d like us to answer,=C2=A0*[*= submit it here.*](https://forms.gle/zEPViEt8Z1aRDWzc6) **Some light reading** ---------------------- =E2=9C=85=C2=A0**Glug glug**: US hyperscalers to guzzle 22% more grid juice= by end of 2025 ([The Register](https://www.theregister.com/2025/10/16/us_d= atacenters_ai_power/)) =E2=9C=85=C2=A0**Good question**: Who really controls AI in an organization= ? ([IT Brew](https://www.itbrew.com/stories/2025/10/16/who-really-controls-= ai-in-an-organization))=C2=A0 =E2=9C=85=C2=A0**Secrets secrets**: AI Chat Data Is History's Most Thorough= Record of Enterprise Secrets. Secure It Wisely. ([Dark Reading](https://ww= w.darkreading.com/application-security/ai-chat-data-is-history-s-most-thoro= ugh-record-of-enterprise-secrets-secure-it-accordingly)) ###**Group therapy**=20 =E2=80=9CI've been screaming about the Windows 10 EOL deadline for two year= s, and here we are with 200 machines still on Win10. It was the can we just= kept kicking. I only got approval to start migrations=C2=A0*last week*, an= d now my CTO is suddenly asking if we can just move to Linux instead. Like = that would be easier at this point. I'm not saying I told you so, but I'm a= lso forwarding every ignored email from 2023.=E2=80=9D =F0=9F=AB=A0=C2=A0*~= Anonymous IT hero* *Do you have an IT horror story?=C2=A0*[*Share here to be featured*](https:= //forms.gle/rhibFZX4B9emGXPXA)*=C2=A0in a future issue.* [ **Tell your story**](https://forms.gle/rhibFZX4B9emGXPXA) Rippling IAM has some new tricks. See how we allow IT leaders to build adap= tive, context-aware policies that evolve automatically with your organizati= on, giving you more security and less administrative burden.=C2=A0 Stick around to the end of our Lunch & Learn deminar, and one lucky attende= e will win a $500 Visa gift card. You=E2=80=99re all lucky, armed with all = that knowledge, but one of you will also have $500. So that=E2=80=99s nice.= =C2=A0[Register now!](https://rippling.registration.goldcast.io/webinar/238= 377a3-ffe5-48c3-89f3-bf189d41a798?rtlid=3D00QUd00000QcSfRMAV) ###**Want free swag?** We=E2=80=99re building a community of IT heroes on our channels in=C2=A0[Ma= cAdmins](https://join.slack.com/t/macadmins/shared_invite/zt-352ap8ifr-v86Y= rFJjxYQ1YIo2M8OmAA)=C2=A0and=C2=A0[Spiceworks](https://community.spiceworks= .com/c/vendors/rippling-it/426). Jump in, say hi, and drop the phrase **=E2= =80=9CThe IT Factor sent me=E2=80=9D** in a comment or post. We=E2=80=99ll = send you a free IT Hero T-shirt, no strings attached. [Tell a friend](https://www.rippling.com/the-it-factor?SubRef=3Dalvarochf@t= raceseis.com) [Terms Apply](https://app.rippling.com/legal/promoterms?rtlid=3D00QUd00000Q= cSfRMAV) If you received this newsletter via an email forward, =C2=A0[Subscribe Here= ](https://www.rippling.com/the-it-factor) [Service Terms](https://app.rippling.com/legal?rtlid=3D00QUd00000QcSfRMAV "= Service Terms")=C2=A0=C2=A0=C2=A0|=C2=A0=C2=A0=C2=A0[Privacy Policy](https:= //app.rippling.com/legal/privacy?rtlid=3D00QUd00000QcSfRMAV)[=C2=A0](https:= //app.rippling.com/privacy)=C2=A0=C2=A0|=C2=A0=C2=A0=C2=A0[Unsubscribe](htt= ps://www.rippling.com/06741456066933719627-22348?email-type=3Dnewsletter "U= nsubscribe") 430 CALIFORNIA ST, SF, CA 94104 =C2=A0 =C2=A0 Rippling Insurance | CA: 0M36087 | NPN: 18578689 [override](https://r.see.rippling.com/mk/un/v2/sh/WCPxRrWByckThluAc3ZDUbPNC= iXKR1KI/hWF9g16hC5Fx) ---------?=_65110-5637466502955 Content-Transfer-Encoding: quoted-printable Content-Type: text/html; charset=UTF-8 =F0=9F=91=8BFarewell to Windo= ws 10 + surviving compliance solo<= style type=3D"text/css" emogrify=3D"no">@media (max-width: 600px) { .gmx-ki= llpill { content: ' \03D1';} .r0-o { border-style: solid !important; 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3D"Rippling

OCTOBER =C2=A02025
<= /a>
<= tr> =
=C2=AD

Matt Lombardo=

Editor

Can you be= lieve there=E2=80=99s only one more week left in cybersecurity awareness mo= nth? Me either. Time flies when you=E2=80=99re not getting hacked.=C2=A0


=F0=9F=AA=A6 So fast, in fact, that the end of the Windows 10= era is already=C2=A0

here.=C2= =A0


=F0=9F=93=8B We=E2=80=99ll hear from a team of one who = passed five audits =E2=80=93 both SOC 2 and ISO 27001 =E2=80=93 at Customer= .io without a single other team member to back him up. How=E2=80=99d he do = it? Scroll down.=C2=A0


=F0=9F=93=85 And fin= ally, we=E2=80=99ve got a jam-packed lineup of webinars in the next two wee= ks, so take a look at what we=E2=80=99ve got on deck and register for which= ever session you can join. They=E2=80=99re cool, we promise.=C2=A0
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=F0=9F=91=8BWe Hardly Knew Ye, Windows 10

=

Say it ain=E2= =80=99t so! Microsoft just officially pulled the plug on Windows 10, leavin= g=C2=A0over 40% of Windows users=C2=A0(!!!) without support. Decisions were made,=C2=A0as were memes.


Many companies will shell out for the year-ish= -long lifeline that is Microsoft=E2=80=99s ESU (Extended Security Updates) = program, and that=E2=80=99ll buy you some time. But now wouldn=E2=80=99t be= the worst time to start putting together a plan.=C2=A0


And just in case you missed this =E2=80=93 a lot of people di= d with all the noise around Windows 10 =E2=80=93 support also ended for Off= ice 2019 and Exchange Server 2019 last week, too. And there=E2=80=99s no ES= U for those two. It=E2=80=99s an extinction event in Redmond, WA.=C2=A0


So if you=E2=80=99re an all-Microsoft shop, no= w would be a good time to take some inventory.=C2=A0


Today: Discovery time. Pull reports on Windows versions, Office= deployments, server OSes, and yes, that SharePoint 2016 instance that the = finance team swears they need. Know your exposure before it knows you.


Tomorrow: Build retrieval workfl= ows for anything that needs to be tractor-beamed back to the mothership. Re= mote employees won't return devices without automated escalation from gentl= e reminders to "Hey! CC'd your manager, thanks for your help.=E2=80=9D=C2= =A0


Next week= : Present the budget bomb. Calculate the costs of replacing what can=E2=80= =99t be updated versus the fees you=E2=80=99ll rack up extending support. T= hrow in the costs of a potential breach, and you=E2=80=99re well on your wa= y to a number that=E2=80=99ll get the C-suite=E2=80=99s sign-off.

Join us tomorrow for a li= ve webinar relevant to any IT team out there who=E2=80=99s working with rem= ote users (which, we would venture a guess, is a lot of you).
=
You=E2=80=99ll hear from a Rippling IT customer at Di= ana Health, who=E2=80=99s using the platform to secure ten 24/7 clinic loca= tions, a full telehealth operation, and a remote corporate workforce, all w= hile maintaining HIPAA compliance. Register now!=

=
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In= troducing: =F0=9F=94=A5=C2=A0Hotkeys=C2=A0
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<= span style=3D"font-weight: 400; font-style: normal; text-decoration: none; = font-family: basel, arial; color: rgb(24, 24, 24);">(I=E2=80=99m working on= a logo. Seriously! I am. Stay tuned.)=C2=A0


=

They=E2=80=99re short videos =E2= =80=93 we aim for a minute or less =E2=80=93 that introduce you to a given = feature or use case that Rippling IT can help you solve. You know, like a keyboard shortcut? Like a hotkey, for insta= nce? I'll see myself out.


<= p style=3D"margin: 0;">Today, we=E2=80=99ve got=C2=A0device policies. Because you don=E2=80= =99t have to manually configure every device for every employee. There's a = better way.
=

Join us next Tuesday, 10/28, for The Rippling = Rundown, where you=E2=80=99ll hear from a number of product leaders and Rip= pling customers on the latest and greatest in the platform and where we=E2= =80=99re headed next. Register now!

=F0=9F=93=8B Surviving Solo Compliance at a Gro= wing Startup


His first piece of advice may be a comfort to some of you out th= ere. Having built an IT function at the company from scratch, all by himsel= f, he went in knowing that it wouldn=E2=80=99t be purely smooth sailing.=C2= =A0

=E2=80=9C= I knew the work would definitely be daunting at times, definitely for sure.= But I also knew frameworks like SOC 2 and ISO 27001 aren't about perfectio= n right off the bat. There will be inconsistencies. There will be missing d= ocumentation."



"Compliance is not just a one-p= erson thing. You need everyone across the entire organization to be with yo= u.=E2=80=9D


So Eldin built a cross-functional team to get it done: a coali= tion of the willing from engineering, legal, finance, and people ops. They = met quarterly. They created templates together. They owned their pieces. An= d when the time came, they put them together.


"In the e= vent the auditors requested evidence, we already had it. We had all of the = evidence gathered already."

At the end of the day, while = Eldin was working as an IT team of one, he made a point of seeking support = elsewhere across the org. According to Eldin, that =E2=80=93 and a seriousl= y impressive slew of automations =E2=80=93 made all the difference.=C2=A0


Facing compliance woes too? Use our=C2=A0= 8-week SOC 2 toolkit=C2=A0to get it all done.=C2=A0


Stay tuned for more advice from today=E2=80=99s IT and security pros ever= y week. And if you have a question you=E2=80=99d like us to answer,=C2=A0submit it here.=

<= th width=3D"100%" valign=3D"top" class=3D"r12-c" style=3D"font-weight: norm= al;">
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Some light reading=

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=E2=9C=85=C2= =A0Glug = glug: US hyperscalers to guzzle 22% more grid juice by end of 20= 25 (The Register)

=


=E2=9C=85=C2=A0Good question: Who re= ally controls AI in an organization? (IT Brew)=C2=A0


=E2=9C=85=C2=A0Secrets secrets: AI Chat Data Is History's Most Thor= ough Record of Enterprise Secrets. Secure It Wisely. (Dark Reading)
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Group therapy

= =E2=80=9CI've been screaming about the Windows 10 EOL deadline for two year= s, and here we are with 200 machines still on Win10. It was the can we just= kept kicking. I only got approval to start migrations=C2=A0last week, and now my = CTO is suddenly asking if we can just move to Linux instead. Like that woul= d be easier at this point. I'm not saying I told you so, but I'm also forwa= rding every ignored email from 2023.=E2=80=9D =F0=9F=AB=A0=C2=A0~ Anonymous IT hero<= /span>


Do you have an= IT horror story?=C2=A0Share here= to be featured=C2=A0in a future issue.
Tell your story

Rippling IAM has some new tricks. See how we = allow IT leaders to build adaptive, context-aware policies that evolve auto= matically with your organization, giving you more security and less adminis= trative burden.=C2=A0


Stick arou= nd to the end of our Lunch & Learn deminar, and one lucky attendee will win= a $500 Visa gift card. You=E2=80=99re all lucky, armed with all that knowl= edge, but one of you will also have $500. So that=E2=80=99s nice.=C2=A0Register now!
<= td valign=3D"top" class=3D"r50-i" style=3D"padding-left: 15px; padding-righ= t: 15px;">
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Wa= nt free swag?

We=E2=80=99re building= a community of IT heroes on our channels in=C2=A0MacAdmins=C2=A0and=C2=A0Spiceworks. Jump in, say hi,= and drop the phrase =E2=80=9CThe IT Factor sent me=E2=80=9D in a comment or post. We=E2=80=99ll send you a free IT Hero T-shirt, no = strings attached.


Tell a friend

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If you received thi= s newsletter via an email forward, =C2=A0Subscribe Here<= /a>

Service Terms=C2=A0=C2=A0=C2=A0|=C2=A0=C2= =A0=C2=A0Privacy Policy=C2=A0=C2=A0=C2=A0<= /span>|=C2=A0=C2=A0=C2=A0Unsubscribe
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430 CALIFORNIA ST, SF, CA 94104

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Rip= pling Insurance | CA: 0M36087 | NPN: 18578689
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