Episode 427: Copilot Cowork Hands-On Experiences

May 07, 2026

Episode Transcript

Welcome to Episode 427 of the Microsoft Cloud IT Pro Podcast. In this episode, Ben and Scott open with a quick look at YAKO (getyako.com), a browser extension built by community member Merrill that replaces the new tab page with a customizable dashboard of Microsoft 365 and cloud links. From there, the conversation turns into an extended follow-up on Copilot Cowork, covering some of their recent hands-on experience with custom skills, artifact management, session crashes tied to an Anthropic API outage, and the friction of working with IRM-protected documents in Copilot Cowork.

The bigger thread running through the episode is data security. Listen in to hear more about considerations for onboarding to Copilot Cowork in its early days.

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Show Notes

Sponsors

	TrustedTech Team is a leading Microsoft Cloud Solution Provider (CSP) specializing in Microsoft Cloud services, Microsoft perpetual licensing, and Microsoft Support Services for medium and enterprise-sized businesses. Their robust team of in-house, U.S.-based Microsoft architects and engineers are certified in all 6/6 Microsoft Solutions Partner Designations in the Microsoft Cloud Partner Program. M365 Licensing Consultation M365 Tenant Assessment Copilot Readiness Assessment
	ShareGate is your migration and governance solution for Microsoft 365. ShareGate helps your teams simplify tenant migrations, get Copilot-ready, and take control of Microsoft 365 governance.
	Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. Nasuni powers the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits.
	Intelligink — Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

See full episode transcriptTranscript is autogenerated by AI

1 00:00:03,600 --> 00:00:06,080 Welcome to episode 427 2 00:00:06,080 --> 00:00:08,820 of the Microsoft Cloud IT Pro podcast, 3 00:00:09,439 --> 00:00:12,419 recorded live on 04/30/2026. 4 00:00:12,639 --> 00:00:14,960 This is a show about Microsoft three sixty 5 00:00:14,960 --> 00:00:17,195 five and Azure from the perspective of IT 6 00:00:17,195 --> 00:00:19,434 pros and end users, where we discuss a 7 00:00:19,434 --> 00:00:21,835 topic or recent news and how it relates 8 00:00:21,835 --> 00:00:24,474 to you. In this episode, Ben and Scott 9 00:00:24,474 --> 00:00:26,875 open with a quick peek at Merrill's latest 10 00:00:26,875 --> 00:00:30,530 project, Yako, a browser extension to make navigating 11 00:00:30,530 --> 00:00:33,750 to your Microsoft three sixty five services quicker. 12 00:00:34,289 --> 00:00:36,770 Then they move into an extended follow-up on 13 00:00:36,770 --> 00:00:39,490 Copilot CoWork and some of the recent hands 14 00:00:39,490 --> 00:00:40,229 on hardships, 15 00:00:40,770 --> 00:00:42,870 artifact management, and integration 16 00:00:43,250 --> 00:00:43,990 with Anthropic, 17 00:00:44,534 --> 00:00:48,214 including a potential security risk related to sensitive 18 00:00:48,214 --> 00:00:48,714 data. 19 00:00:50,854 --> 00:00:52,934 So we're trying something new today, Scott. We 20 00:00:52,934 --> 00:00:54,155 are recording in Riverside 21 00:00:54,695 --> 00:00:56,375 so that we can maybe try to do 22 00:00:56,375 --> 00:00:59,320 some shorts. And who knows? Maybe we'll even 23 00:00:59,619 --> 00:01:02,259 broadcast live to LinkedIn and YouTube here in 24 00:01:02,259 --> 00:01:04,659 the future. Start incorporating some video. I've been 25 00:01:04,659 --> 00:01:06,659 told we should do actually, nobody's told me 26 00:01:06,659 --> 00:01:08,439 we should do video. The SEO 27 00:01:09,060 --> 00:01:12,765 people and everybody that grows podcasts tell me 28 00:01:12,765 --> 00:01:14,924 we should do video. Our AI overlords are 29 00:01:14,924 --> 00:01:16,844 back. They're just gonna have us do this 30 00:01:16,844 --> 00:01:18,525 until we're done with it. We've tried it 31 00:01:18,525 --> 00:01:20,924 before and then quit. I don't know, Scott. 32 00:01:20,924 --> 00:01:23,984 Maybe this time it'll stick. Maybe Riverside will 33 00:01:24,125 --> 00:01:24,944 make it easier. 34 00:01:25,450 --> 00:01:27,770 The AI has definitely made some of it. 35 00:01:27,770 --> 00:01:30,090 It's compelling stuff here. We we should probably 36 00:01:30,090 --> 00:01:30,670 get into, 37 00:01:31,130 --> 00:01:32,969 get get into our topic of the day. 38 00:01:32,969 --> 00:01:35,210 Yeah. Before we get into our topic, though, 39 00:01:35,210 --> 00:01:37,069 did you see Merrill's latest 40 00:01:37,930 --> 00:01:39,710 invention development project, 41 00:01:40,344 --> 00:01:43,644 etcetera? I have not. Okay. So go into 42 00:01:43,944 --> 00:01:46,765 whatever browser you use and go search for 43 00:01:47,305 --> 00:01:47,884 Yako, y a 44 00:01:49,944 --> 00:01:51,704 c o, or you can go to the 45 00:01:51,704 --> 00:01:54,299 website, get Yako, yaya, 46 00:01:54,299 --> 00:01:56,459 not c,yako,.com. 47 00:01:56,459 --> 00:01:57,819 I'll send you a link. I should've done 48 00:01:57,819 --> 00:01:59,500 this earlier because now I don't know where 49 00:01:59,500 --> 00:02:01,819 our Teams chat is. It is a browser 50 00:02:01,819 --> 00:02:02,319 extension 51 00:02:03,019 --> 00:02:03,519 that 52 00:02:03,819 --> 00:02:06,459 changes the home page of your browser. So 53 00:02:06,459 --> 00:02:08,719 he created it for Edge, Chrome, and Firefox. 54 00:02:09,235 --> 00:02:10,914 And now when you click a new tab 55 00:02:10,914 --> 00:02:13,574 in your browser, it gives you 56 00:02:14,194 --> 00:02:14,675 the 57 00:02:15,074 --> 00:02:16,354 like, it gives you a bunch of links 58 00:02:16,354 --> 00:02:19,715 that you can customize to whatever Office March 59 00:02:20,034 --> 00:02:23,469 well, Microsoft Cloud, really, Cloud links. So, like, 60 00:02:23,469 --> 00:02:23,969 mine, 61 00:02:24,349 --> 00:02:25,550 I hit a new tab, and I can 62 00:02:25,550 --> 00:02:27,569 pick OneDrive, Outlook, Loop, Copilot, 63 00:02:27,949 --> 00:02:29,889 Azure, Sentinel, Intune, 64 00:02:30,509 --> 00:02:31,409 Admin Center, 65 00:02:31,870 --> 00:02:32,370 all 66 00:02:32,750 --> 00:02:34,909 the different things. Then I can customize what 67 00:02:34,909 --> 00:02:36,430 I want on there. That's a nifty one. 68 00:02:36,430 --> 00:02:38,050 I can see how that would be helpful 69 00:02:38,485 --> 00:02:40,025 in a work context. 70 00:02:40,405 --> 00:02:41,525 I I don't know that I'd use it 71 00:02:41,525 --> 00:02:43,284 too much on my personal one, but def 72 00:02:43,364 --> 00:02:45,284 definitely on the work side of things. Yeah. 73 00:02:45,284 --> 00:02:46,564 I don't know that it's a personal one, 74 00:02:46,564 --> 00:02:49,044 but for work and, frankly, I don't really 75 00:02:49,044 --> 00:02:50,965 care about the news that normally pops up, 76 00:02:50,965 --> 00:02:53,064 and I know you can tweak it. And 77 00:02:53,284 --> 00:02:55,560 I don't really wanna set portal to office.com 78 00:02:55,560 --> 00:02:57,079 since that doesn't even get me to my 79 00:02:57,079 --> 00:02:58,939 apps anymore. It just gets me to Copilot 80 00:02:59,000 --> 00:02:59,500 chat. 81 00:03:00,840 --> 00:03:03,639 Admin.microsoft.com. 82 00:03:03,879 --> 00:03:05,500 Yeah. Or use, like, Copilot 83 00:03:05,879 --> 00:03:08,205 or quad or chat GPT or whatever and 84 00:03:08,365 --> 00:03:10,444 pin pin that one in there. I use 85 00:03:10,444 --> 00:03:13,805 the Copilot one on personal edge. Like, it 86 00:03:13,805 --> 00:03:15,564 tends to do pretty good. The only thing 87 00:03:15,564 --> 00:03:17,884 I hate about it is it uses Bing 88 00:03:17,884 --> 00:03:19,884 as the search engine. So if it can't, 89 00:03:19,884 --> 00:03:22,205 like, auto resolve to yako.com 90 00:03:22,205 --> 00:03:23,669 or get yako.com, 91 00:03:23,750 --> 00:03:25,509 it fires me off into Bing. Then I'm 92 00:03:25,509 --> 00:03:27,530 left with Bing search results. 93 00:03:28,069 --> 00:03:29,830 I don't I don't need Bing search results 94 00:03:29,830 --> 00:03:32,310 in my life. But yeah. No. Cool. I'll 95 00:03:32,310 --> 00:03:35,189 have to try this one out, and we'll 96 00:03:35,189 --> 00:03:38,650 put a link to gityako.com. 97 00:03:39,715 --> 00:03:40,215 G, 98 00:03:40,514 --> 00:03:44,115 yeah, getyako.com 99 00:03:44,115 --> 00:03:46,354 by Merrill. Nice one. Again, probably more for 100 00:03:46,354 --> 00:03:47,955 work than personal because it doesn't have any 101 00:03:47,955 --> 00:03:49,555 of the well, I can't remember. Does it 102 00:03:49,555 --> 00:03:51,395 have personal m three sixty five stuff in 103 00:03:51,395 --> 00:03:53,155 there? I would have to go 104 00:03:53,750 --> 00:03:55,669 look. Oh, you can also switch it from 105 00:03:55,669 --> 00:03:57,750 classic icons. I know we've talked about these 106 00:03:57,750 --> 00:03:59,509 before if you want a new tab to 107 00:03:59,509 --> 00:04:01,669 be like msportals.io 108 00:04:01,669 --> 00:04:03,430 or cmd.ms. 109 00:04:03,430 --> 00:04:05,110 Yeah. I did see that. So so that's 110 00:04:05,110 --> 00:04:07,355 another project that Merrill has out there with 111 00:04:07,355 --> 00:04:09,835 the with the short links and things like 112 00:04:09,835 --> 00:04:11,435 that. So that that could be a helpful 113 00:04:11,435 --> 00:04:13,115 one as well. Oh, it does have some 114 00:04:13,115 --> 00:04:15,514 of the consumer stuff. So if you are 115 00:04:15,514 --> 00:04:17,514 just at home and you wanna do consumer 116 00:04:17,514 --> 00:04:19,050 stuff in it, you can do that as 117 00:04:19,870 --> 00:04:20,370 well. 118 00:04:21,189 --> 00:04:23,990 You're out of time. Copilot needs to be 119 00:04:23,990 --> 00:04:27,110 deployed ASAP, but is your tenant really ready 120 00:04:27,110 --> 00:04:30,329 for it? Years of data, permissions, and users 121 00:04:30,470 --> 00:04:33,024 lurk in its shadows, ready to be exposed 122 00:04:33,024 --> 00:04:33,845 by AI. 123 00:04:34,225 --> 00:04:37,024 Sharegate Protect sees it all, so you can 124 00:04:37,024 --> 00:04:39,985 find the exposure risks, fix them fast, and 125 00:04:39,985 --> 00:04:41,764 deploy AI with confidence. 126 00:04:42,225 --> 00:04:45,660 Microsoft three sixty five governance. We got this. 127 00:04:45,899 --> 00:04:50,560 Learn more at sharegate.com/governance. 128 00:04:53,339 --> 00:04:54,860 Now we can get into our topic if 129 00:04:54,860 --> 00:04:56,779 you want. That was just a nifty thing 130 00:04:56,779 --> 00:04:58,779 that popped up in my feed the other 131 00:04:58,779 --> 00:05:00,535 day and I was been playing with. And 132 00:05:00,535 --> 00:05:02,154 maybe a little bit of follow-up. So 133 00:05:02,535 --> 00:05:05,035 last time we recorded, we kinda talked about 134 00:05:05,175 --> 00:05:07,895 the co work situation and Claude co work 135 00:05:07,895 --> 00:05:09,274 and CoPilot co work. 136 00:05:09,574 --> 00:05:10,074 And 137 00:05:10,535 --> 00:05:12,214 that definitely sent me down the path of, 138 00:05:12,214 --> 00:05:14,189 like, hey. Let me play a little bit 139 00:05:14,189 --> 00:05:17,230 more with CoPilot CoWork and kinda see where 140 00:05:17,230 --> 00:05:18,670 I could see how far I could get 141 00:05:18,670 --> 00:05:20,270 with some of the stuff we had talked 142 00:05:20,270 --> 00:05:22,529 about, like, maybe, like, the limitations 143 00:05:22,830 --> 00:05:24,350 of not being able to interact with your 144 00:05:24,350 --> 00:05:26,750 local desktop or or local resources, all that 145 00:05:26,750 --> 00:05:28,204 kind of stuff. So 146 00:05:28,985 --> 00:05:31,865 custom skills in Copilot Cowork are kind of 147 00:05:31,865 --> 00:05:33,884 broken right now. They're they're a little frustrating 148 00:05:34,024 --> 00:05:36,604 to to work with along the way. Definitely 149 00:05:36,665 --> 00:05:39,884 ran into the I'm very used to kinda 150 00:05:40,250 --> 00:05:40,750 prompting 151 00:05:41,209 --> 00:05:43,289 LLMs at this point or a lot of 152 00:05:43,289 --> 00:05:46,089 these tools with questions to kinda help me 153 00:05:46,089 --> 00:05:47,689 refine a prompt and come up with a 154 00:05:47,689 --> 00:05:49,930 way to generate, like, the artifacts that you 155 00:05:49,930 --> 00:05:51,850 want. So rather than saying go in and 156 00:05:51,850 --> 00:05:54,145 build me this, it's ask me a couple 157 00:05:54,145 --> 00:05:55,745 questions that are gonna help. Like, here's the 158 00:05:55,745 --> 00:05:56,965 outcome I wanna achieve. 159 00:05:57,345 --> 00:05:58,324 So in, 160 00:05:58,705 --> 00:06:01,345 like, in the case of, say, like, Claude 161 00:06:01,345 --> 00:06:01,845 Code 162 00:06:02,225 --> 00:06:02,725 or 163 00:06:03,105 --> 00:06:05,905 GitHub Copilot CLI, things like that, or GitHub 164 00:06:05,905 --> 00:06:08,064 Copilot chat, it's very easy to go in 165 00:06:08,064 --> 00:06:09,939 and say, I would like to build a 166 00:06:09,939 --> 00:06:11,560 new skill that does 167 00:06:11,860 --> 00:06:13,779 blah blah blah. And then it will actually 168 00:06:13,779 --> 00:06:15,319 kinda ask you a couple questions, 169 00:06:15,699 --> 00:06:17,699 and it will frame out the markdown for 170 00:06:17,699 --> 00:06:19,460 you, and it will write it to the 171 00:06:19,460 --> 00:06:21,699 right directory for you, like, to the point 172 00:06:21,699 --> 00:06:22,904 where it where you can do 173 00:06:23,625 --> 00:06:26,185 install to just my local session or install 174 00:06:26,185 --> 00:06:29,305 this globally kinda thing. And Copilot Coburg kinda 175 00:06:29,305 --> 00:06:30,904 surprised me. It walked me in and it 176 00:06:30,904 --> 00:06:32,665 said, oh, you wanna create a new skill. 177 00:06:32,665 --> 00:06:34,425 This is great. I'll go create a new 178 00:06:34,425 --> 00:06:35,785 skill for you. What do you wanna call 179 00:06:35,785 --> 00:06:37,464 it? What do you want the description to 180 00:06:37,464 --> 00:06:39,459 be? And I already had all this markdown 181 00:06:39,459 --> 00:06:41,220 and stuff that I wanted to pump into 182 00:06:41,220 --> 00:06:43,959 it. So boom. Great. Click the go button, 183 00:06:44,100 --> 00:06:46,339 does its cheeky. I'm thinking about it and 184 00:06:46,339 --> 00:06:48,500 thinking and spinning the gears. And then it 185 00:06:48,500 --> 00:06:50,740 spits out an output for me, which is 186 00:06:50,740 --> 00:06:53,504 a skill quality report. So it gave me 187 00:06:53,504 --> 00:06:56,064 this very nice HTML file that said, I 188 00:06:56,064 --> 00:06:57,205 created your skill, 189 00:06:57,584 --> 00:07:01,185 and your skill has an 83, 84% score 190 00:07:01,185 --> 00:07:02,305 or whatever it is. Right? So it gave 191 00:07:02,305 --> 00:07:04,545 me this, like, nice dashboard that said, your 192 00:07:04,545 --> 00:07:06,644 skill is gonna be awesome and it passes. 193 00:07:06,800 --> 00:07:08,399 I don't know what it passes because it 194 00:07:08,399 --> 00:07:10,319 just generated me an HTML file that said 195 00:07:10,319 --> 00:07:12,560 my my my skill was really good. But 196 00:07:12,560 --> 00:07:13,620 it also hallucinated 197 00:07:13,920 --> 00:07:16,000 that it had ever created the skill. So 198 00:07:16,000 --> 00:07:18,000 it never actually went and created, like, the 199 00:07:18,000 --> 00:07:19,759 skill dot m d and put it in 200 00:07:19,759 --> 00:07:21,920 the right folder in my OneDrive and did 201 00:07:21,920 --> 00:07:22,485 all that stuff. 202 00:07:23,044 --> 00:07:24,724 So great that it told me my skill 203 00:07:24,724 --> 00:07:26,964 was awesome, and it generated a report that 204 00:07:26,964 --> 00:07:29,464 my skill was awesome. Not so great that 205 00:07:29,524 --> 00:07:31,685 it didn't actually generate my skill. It didn't 206 00:07:31,685 --> 00:07:33,925 actually create a skill? Maybe it did. Maybe 207 00:07:33,925 --> 00:07:36,324 it's in someone else's OneDrive. That was number 208 00:07:36,324 --> 00:07:39,449 one. Number two is actually finally did get 209 00:07:39,449 --> 00:07:40,970 that skill created. Had to go do it 210 00:07:40,970 --> 00:07:43,129 manually, provision it into my OneDrive. It's a 211 00:07:43,129 --> 00:07:46,990 little weird in the cowork frontier agent today 212 00:07:47,290 --> 00:07:49,930 because sometimes it sees your skills in your 213 00:07:49,930 --> 00:07:52,785 OneDrive, and sometimes it does not. So when 214 00:07:52,785 --> 00:07:54,625 you go and you do, like, slash commands 215 00:07:54,625 --> 00:07:57,105 in Copilot co work, you're presented with an 216 00:07:57,105 --> 00:07:59,444 interface of, like, people, skills, 217 00:07:59,824 --> 00:08:02,464 files, and these various things. So the very 218 00:08:02,464 --> 00:08:03,985 first time I created this skill, I went 219 00:08:03,985 --> 00:08:05,345 out there and I went and I just 220 00:08:05,345 --> 00:08:07,819 popped it into my OneDrive. I closed Copilot 221 00:08:07,959 --> 00:08:10,199 down, just the Copilot m three sixty five 222 00:08:10,199 --> 00:08:12,040 Copilot app, which I was just happened to 223 00:08:12,040 --> 00:08:14,279 be using, but it's that web wrapper. Loaded 224 00:08:14,279 --> 00:08:17,080 it back up, slash command. Oh, look. There's 225 00:08:17,080 --> 00:08:18,759 my skill. That's awesome. Like, didn't need to 226 00:08:18,759 --> 00:08:21,305 navigate around a bunch or do anything. Came 227 00:08:21,305 --> 00:08:22,044 back and 228 00:08:22,504 --> 00:08:24,104 so I did a quick chat with it 229 00:08:24,104 --> 00:08:26,125 just to see, like, okay. Does this work? 230 00:08:26,264 --> 00:08:28,584 Cool. It generated some output. Looks like it 231 00:08:28,584 --> 00:08:29,865 did the right thing that I wanted it 232 00:08:29,865 --> 00:08:31,224 to do. So then I spun up a 233 00:08:31,224 --> 00:08:33,704 new chat. Now mind you, I didn't close 234 00:08:33,704 --> 00:08:35,889 m three sixty five chat down. I didn't 235 00:08:35,889 --> 00:08:38,289 change anything in my OneDrive. Okay. Just a 236 00:08:38,289 --> 00:08:40,529 new session. Just a new chat session because 237 00:08:40,529 --> 00:08:42,129 now I'm like, oh, cool. This still works. 238 00:08:42,129 --> 00:08:43,570 Let me actually go, like, fire off and 239 00:08:43,570 --> 00:08:45,649 do what I wanted to do. New chat? 240 00:08:45,649 --> 00:08:47,454 I don't know about your skill. I've never 241 00:08:47,454 --> 00:08:48,855 seen this thing in the world, like, in 242 00:08:48,855 --> 00:08:50,294 my life. I I don't know what it 243 00:08:50,294 --> 00:08:51,735 is and what's going on. So you do 244 00:08:51,735 --> 00:08:53,735 the slash command, not there in the slash 245 00:08:53,735 --> 00:08:57,095 command. You actually knit browse straight over to 246 00:08:57,095 --> 00:08:58,394 the skills tab 247 00:08:58,774 --> 00:09:01,809 from the slash command, not there. But you 248 00:09:01,889 --> 00:09:03,730 I was able to say in my co 249 00:09:03,730 --> 00:09:05,970 work session, do you know about this skill? 250 00:09:05,970 --> 00:09:07,809 Can you please, like, use it when I 251 00:09:07,809 --> 00:09:09,809 put this what I wanna do in here? 252 00:09:09,809 --> 00:09:12,049 So it it eventually kinda wrangled itself. So 253 00:09:12,049 --> 00:09:14,289 I think that skills experience has a little 254 00:09:14,289 --> 00:09:16,209 bit of refinement to do, maybe something for 255 00:09:16,209 --> 00:09:18,105 folks to watch out for. The other thing 256 00:09:18,105 --> 00:09:18,605 that's 257 00:09:19,225 --> 00:09:21,705 been, I think, kind of getting on my 258 00:09:21,705 --> 00:09:24,665 nerves a little bit is as you're in 259 00:09:24,665 --> 00:09:28,105 Copilot Cowork and you're generating artifacts, so like 260 00:09:28,105 --> 00:09:30,105 in that very first run where it generated 261 00:09:30,105 --> 00:09:32,105 a skill report for me or or what 262 00:09:32,105 --> 00:09:34,035 I was trying to do with this custom 263 00:09:34,035 --> 00:09:36,257 skill that I spun out, it was ultimately 264 00:09:36,257 --> 00:09:38,478 spitting out some HTML files and some markdown 265 00:09:38,478 --> 00:09:40,700 for me as, like, an output. So those 266 00:09:40,700 --> 00:09:42,921 all go into your session, and you see 267 00:09:42,921 --> 00:09:44,587 them kind of in the Cowork, 268 00:09:45,424 --> 00:09:47,745 in in the co work frontier agent interface, 269 00:09:47,745 --> 00:09:48,705 like, it has a little bit of a 270 00:09:48,705 --> 00:09:50,945 different interface than the chat interface, and it 271 00:09:50,945 --> 00:09:52,865 says, here's your inputs, here's your outputs, blah 272 00:09:52,865 --> 00:09:55,264 blah blah. Good luck because well, at least 273 00:09:55,264 --> 00:09:57,584 in whatever build I'm on that's pushed out 274 00:09:57,584 --> 00:10:00,679 today or as of today, you cannot, like, 275 00:10:00,820 --> 00:10:03,300 right click those things and open in OneDrive. 276 00:10:03,300 --> 00:10:04,899 There is a little drop down like like 277 00:10:04,899 --> 00:10:06,980 an ellipsis there to click it and say 278 00:10:06,980 --> 00:10:08,740 open in OneDrive. Doesn't work for me at 279 00:10:08,740 --> 00:10:10,740 all. So then you gotta go manually browse 280 00:10:10,740 --> 00:10:12,500 your OneDrive. So you go into your OneDrive, 281 00:10:12,500 --> 00:10:14,385 you go into your documents folder, you go 282 00:10:14,385 --> 00:10:16,341 into your co work folder. And then in 283 00:10:16,341 --> 00:10:18,296 your co work folder, well, you've got skills, 284 00:10:18,296 --> 00:10:20,251 which is where you load your custom skill, 285 00:10:20,251 --> 00:10:22,207 and then you've got sessions. And then each 286 00:10:22,207 --> 00:10:24,162 session is a GUID. So if you do 287 00:10:24,162 --> 00:10:26,279 multiple chats per day or anything 288 00:10:26,899 --> 00:10:28,500 more than, like, one or two with co 289 00:10:28,500 --> 00:10:30,580 work for the day, now you have these 290 00:10:30,580 --> 00:10:32,980 folders that are just GUIDs. And, hopefully, you 291 00:10:32,980 --> 00:10:35,379 can figure out by timestamp which one is 292 00:10:35,379 --> 00:10:37,379 the right folder because you have to browse 293 00:10:37,379 --> 00:10:39,139 into that GUID folder, and then there's an 294 00:10:39,139 --> 00:10:41,245 outputs folder in there, and then that's where 295 00:10:41,245 --> 00:10:44,704 your artifacts end up. So it's a 296 00:10:45,404 --> 00:10:47,404 it's got some rough edges and some friction 297 00:10:47,404 --> 00:10:50,684 today. And it immediately drew drove me back 298 00:10:50,684 --> 00:10:53,964 to GitHub Copilot CLI, at least, because I 299 00:10:53,964 --> 00:10:56,044 I have access to that or GitHub Copilot, 300 00:10:56,044 --> 00:10:56,429 I guess. 301 00:10:57,470 --> 00:10:59,889 And the other thing is I was hoping 302 00:11:00,750 --> 00:11:01,649 that because 303 00:11:02,190 --> 00:11:02,690 Cowork 304 00:11:03,230 --> 00:11:03,730 is 305 00:11:04,190 --> 00:11:04,929 in the 306 00:11:05,629 --> 00:11:08,589 cloud ecosystem to start, that it would be 307 00:11:08,589 --> 00:11:10,129 able to get by some limitations 308 00:11:10,669 --> 00:11:12,585 that I potentially run into in my day 309 00:11:12,585 --> 00:11:14,184 to day being on the CLI or the 310 00:11:14,184 --> 00:11:14,684 desktop. 311 00:11:14,985 --> 00:11:17,245 And probably one of the biggest ones 312 00:11:17,625 --> 00:11:18,925 is I often have, 313 00:11:19,304 --> 00:11:22,045 like, multiple artifacts, could be presentations, 314 00:11:22,425 --> 00:11:25,070 Word documents, excels, things like that, that I 315 00:11:25,070 --> 00:11:27,309 kinda wanna, like, iterate over and riff on 316 00:11:27,309 --> 00:11:30,029 and come out with those ideas and go 317 00:11:30,029 --> 00:11:32,210 back and forth on my thinking around them. 318 00:11:32,269 --> 00:11:33,950 So on the desktop, I run into a 319 00:11:33,950 --> 00:11:36,210 lot of issues because I have my OneDrive 320 00:11:36,350 --> 00:11:38,754 and I have things synced and both my 321 00:11:38,754 --> 00:11:41,315 work OneDrive and then I use shortcuts a 322 00:11:41,315 --> 00:11:43,715 bunch too, so I have shortcuts back to 323 00:11:43,715 --> 00:11:46,595 SharePoint sites. A lot of the content that 324 00:11:46,595 --> 00:11:48,595 I iterate on day over day and throughout 325 00:11:48,595 --> 00:11:49,894 my day is 326 00:11:50,514 --> 00:11:53,339 IRM ed. So it has some kind of 327 00:11:53,399 --> 00:11:57,019 information rights management or, like, MIP information protection. 328 00:11:57,159 --> 00:11:59,399 Encryption on the files. Yep. Yeah. So when 329 00:11:59,399 --> 00:12:01,080 you're on your desktop and you're sitting there 330 00:12:01,080 --> 00:12:03,720 in, like, GitHub Copilot CLI, well, it's got 331 00:12:03,720 --> 00:12:05,644 a skill to read Word documents. Just 332 00:12:06,345 --> 00:12:07,085 uses the anthropic 333 00:12:07,785 --> 00:12:08,285 word 334 00:12:08,745 --> 00:12:10,684 skill, but that can only read nonencrypted content. 335 00:12:10,865 --> 00:12:13,465 It can't even though it has your user 336 00:12:13,465 --> 00:12:15,065 contacts and you're saying do this or go 337 00:12:15,065 --> 00:12:17,384 into my, like, physical folder on my OneDrive 338 00:12:17,384 --> 00:12:19,240 kinda thing, it can't do it. So I 339 00:12:19,240 --> 00:12:21,240 was kinda hoping that, like, Cowork would maybe 340 00:12:21,240 --> 00:12:22,600 help solve that for me, and I could 341 00:12:22,600 --> 00:12:24,519 just rethink some of the skills I use 342 00:12:24,519 --> 00:12:26,759 in the cloud world. Cowork can't read my 343 00:12:26,759 --> 00:12:29,399 protected documents either. It just blows up and 344 00:12:29,399 --> 00:12:31,399 says, sorry. I can't do this. Is it 345 00:12:31,399 --> 00:12:33,420 because it's sending it over 346 00:12:33,894 --> 00:12:36,394 to Anthropic into Claude versus 347 00:12:37,014 --> 00:12:39,514 when you use the GPT models that's staying 348 00:12:39,654 --> 00:12:40,154 in 349 00:12:40,534 --> 00:12:42,855 the Azure data centers and it's going to 350 00:12:42,855 --> 00:12:45,434 the models internally? That would be my assumption 351 00:12:45,894 --> 00:12:47,195 if that's the case because 352 00:12:47,700 --> 00:12:49,240 those MIP protected documents, 353 00:12:49,940 --> 00:12:52,440 I can use in things like Copilot notebooks 354 00:12:52,820 --> 00:12:54,980 when I'm in GPT mode. And then, oh, 355 00:12:54,980 --> 00:12:57,240 yeah. We should also talk about so, Anthropic 356 00:12:57,300 --> 00:12:59,059 had an outage earlier this week on their 357 00:12:59,059 --> 00:12:59,960 API surface, 358 00:13:00,315 --> 00:13:01,835 and it happened to be when I was 359 00:13:01,835 --> 00:13:03,274 in the middle of one of my Copilot 360 00:13:03,274 --> 00:13:04,174 co work sessions, 361 00:13:04,715 --> 00:13:07,514 completely bombed out. Like, the session crashed, and 362 00:13:07,514 --> 00:13:08,715 if I try and go back into that 363 00:13:08,715 --> 00:13:09,995 chat now, I just end up on a 364 00:13:09,995 --> 00:13:12,394 page that says, sorry, like, sorry, Dave. I 365 00:13:12,394 --> 00:13:13,995 can't do this right now. Can you sign 366 00:13:13,995 --> 00:13:16,350 back in? Like, I am signed in. But 367 00:13:16,350 --> 00:13:18,049 I I basically just lost 368 00:13:18,429 --> 00:13:19,950 the ability to go back in and see 369 00:13:19,950 --> 00:13:21,730 any of that chat history or anything 370 00:13:22,429 --> 00:13:24,750 for that session that's out there. So that 371 00:13:24,750 --> 00:13:26,590 that that was an interesting moment for me 372 00:13:26,590 --> 00:13:28,110 as well because I was trying to debug 373 00:13:28,110 --> 00:13:29,629 it. Like, what happened and what's going on? 374 00:13:29,629 --> 00:13:30,914 Is m three sixty five 375 00:13:31,714 --> 00:13:33,074 down right now? Like, why is just this 376 00:13:33,074 --> 00:13:36,134 one chat broken? And it turns out it 377 00:13:36,195 --> 00:13:37,495 coincided exactly 378 00:13:38,115 --> 00:13:39,334 with the anthropic 379 00:13:40,115 --> 00:13:42,134 API outage. So it was a good reminder 380 00:13:42,195 --> 00:13:44,434 for me of, like, that mental model of, 381 00:13:44,434 --> 00:13:46,294 like, when you're in Copilot Cowork, 382 00:13:46,690 --> 00:13:49,570 you are, I I guess, using just the 383 00:13:49,570 --> 00:13:50,710 anthropic APIs. 384 00:13:51,170 --> 00:13:52,769 So a lot of that stuff does start 385 00:13:52,769 --> 00:13:54,850 to click then about, like, oh, hey. I 386 00:13:54,850 --> 00:13:58,230 can't read and or open that IRM document 387 00:13:58,690 --> 00:14:01,090 and all those kinds of things. So that 388 00:14:01,170 --> 00:14:04,605 that's a, like, funny, like, I guess, limitation, 389 00:14:04,985 --> 00:14:07,225 but that I just I was not prepared 390 00:14:07,225 --> 00:14:08,665 for and I did not have in my 391 00:14:08,665 --> 00:14:11,725 head to even think about, here's one more 392 00:14:11,945 --> 00:14:14,105 modality or, like, mental model that I need 393 00:14:14,105 --> 00:14:15,325 to carry as a user 394 00:14:15,705 --> 00:14:16,205 into 395 00:14:16,745 --> 00:14:18,059 leveraging these tools. 396 00:14:19,659 --> 00:14:22,720 If you're managing file storage today, you've probably 397 00:14:22,779 --> 00:14:25,419 felt the pressure. Refresh cycles are harder to 398 00:14:25,419 --> 00:14:28,860 plan, costs and complexity are increasing, especially as 399 00:14:28,860 --> 00:14:30,960 file workloads scale across regions. 400 00:14:31,334 --> 00:14:34,615 That's why Microsoft customers trust Nasuni as an 401 00:14:34,615 --> 00:14:36,235 Azure certified software. 402 00:14:36,615 --> 00:14:39,654 Nasuni provides a global file system designed for 403 00:14:39,654 --> 00:14:40,954 enterprise scale environments, 404 00:14:41,334 --> 00:14:44,774 keeping file data secure, governed, and accessible across 405 00:14:44,774 --> 00:14:47,879 Azure environments without added infrastructure complexity. 406 00:14:48,259 --> 00:14:51,379 It's the foundation to keep your unstructured data 407 00:14:51,379 --> 00:14:54,740 stable even as your infrastructure evolves. To see 408 00:14:54,740 --> 00:14:56,740 how much you could save while keeping your 409 00:14:56,740 --> 00:15:02,345 initiatives on track, visit nasuni.com/tco. 410 00:15:02,345 --> 00:15:07,004 That's nasuni.com/tco. 411 00:15:08,345 --> 00:15:10,425 So do you want to talk about our 412 00:15:10,425 --> 00:15:11,865 topic, or do you want me to bring 413 00:15:11,865 --> 00:15:14,090 up something that popped into my head since 414 00:15:14,090 --> 00:15:15,690 we're on this topic and you brought that 415 00:15:15,690 --> 00:15:17,950 up? I mean, it's your show. Not really. 416 00:15:18,090 --> 00:15:20,330 Keep going with this. So this brings up 417 00:15:20,330 --> 00:15:22,750 an interesting thought then. Right? Because 418 00:15:23,929 --> 00:15:25,230 that would also 419 00:15:26,184 --> 00:15:27,404 seem to imply 420 00:15:28,105 --> 00:15:29,964 that your chat session, 421 00:15:30,504 --> 00:15:32,684 is it not being stored 422 00:15:33,065 --> 00:15:35,865 in Microsoft three sixty five? So then, like, 423 00:15:35,865 --> 00:15:37,404 did that get corrupted 424 00:15:38,024 --> 00:15:40,440 in Microsoft three sixty five data, or is 425 00:15:40,440 --> 00:15:42,679 it the fact that Microsoft three sixty five 426 00:15:42,679 --> 00:15:46,379 to earlier point can't reach back out to 427 00:15:46,679 --> 00:15:47,420 the API 428 00:15:47,960 --> 00:15:50,779 to grab that session from Claude? 429 00:15:51,160 --> 00:15:53,000 In which case, if all that data's in 430 00:15:53,000 --> 00:15:53,500 Claude, 431 00:15:54,040 --> 00:15:55,019 what does that 432 00:15:55,335 --> 00:15:55,835 start 433 00:15:56,295 --> 00:15:57,754 implying for things 434 00:15:58,695 --> 00:15:59,514 like auditing 435 00:15:59,894 --> 00:16:00,394 and 436 00:16:01,495 --> 00:16:01,995 retention 437 00:16:02,615 --> 00:16:03,115 and 438 00:16:04,134 --> 00:16:04,634 sensitivity 439 00:16:05,014 --> 00:16:08,295 labels when it comes to chat? Like, this 440 00:16:08,295 --> 00:16:10,295 is something, and I don't know if I 441 00:16:10,295 --> 00:16:12,860 should go pop open mine while we're talking, 442 00:16:12,860 --> 00:16:13,360 is 443 00:16:14,779 --> 00:16:16,399 do your clogged conversations 444 00:16:17,259 --> 00:16:18,000 in Cowork 445 00:16:18,539 --> 00:16:21,759 function the same way that a conversation 446 00:16:22,059 --> 00:16:24,575 would in a GPT model when it comes 447 00:16:24,575 --> 00:16:27,934 to sensitive information and sensitive content and, I 448 00:16:27,934 --> 00:16:29,634 guess, almost like that data 449 00:16:30,254 --> 00:16:31,315 sovereign sovereignty 450 00:16:32,335 --> 00:16:33,154 data sovereignty 451 00:16:33,615 --> 00:16:35,875 type scenario. I would imagine, 452 00:16:36,410 --> 00:16:37,309 and this is conjecture 453 00:16:37,690 --> 00:16:39,549 because I haven't seen it, like, formally documented. 454 00:16:39,610 --> 00:16:41,610 But today, when you're in an m three 455 00:16:41,610 --> 00:16:44,269 sixty five tenant, you can have the OpenAI 456 00:16:44,330 --> 00:16:46,570 and GPT models kinda, like, by default. That's 457 00:16:46,570 --> 00:16:48,855 your default mode. You have to go and 458 00:16:49,095 --> 00:16:52,714 explicitly enable anthropic and basically sign the legalese 459 00:16:52,855 --> 00:16:54,534 that you're good with your data You're using 460 00:16:54,534 --> 00:16:55,274 that. Leaving 461 00:16:55,654 --> 00:16:58,315 the boundary of Microsoft's cloud because you are 462 00:16:58,454 --> 00:16:58,954 chatting 463 00:16:59,334 --> 00:17:02,294 with a model that at least is hosted. 464 00:17:02,294 --> 00:17:04,250 So even if you're not sending the data 465 00:17:04,250 --> 00:17:06,250 out, you're still sending the chat out. So 466 00:17:06,250 --> 00:17:09,049 if you're chatting about something that's potentially sensitive 467 00:17:09,049 --> 00:17:11,130 to your business, that would just be passed 468 00:17:11,130 --> 00:17:14,569 in natural language, right, via your prompt over 469 00:17:14,569 --> 00:17:15,069 to 470 00:17:15,529 --> 00:17:17,845 over to that side of things. So I 471 00:17:17,845 --> 00:17:18,424 I know, 472 00:17:19,044 --> 00:17:21,924 you know, organizationally where I am, like, there 473 00:17:21,924 --> 00:17:24,565 there is a big difference in functionality between 474 00:17:24,565 --> 00:17:27,044 folks in The US and Europe because we 475 00:17:27,044 --> 00:17:30,404 haven't lit up anthropic due to GDPR and 476 00:17:30,404 --> 00:17:32,565 things like that for those for that set 477 00:17:32,565 --> 00:17:34,920 of users. So that that that does make 478 00:17:34,920 --> 00:17:37,480 it tough. Like, some things potentially aren't available 479 00:17:37,480 --> 00:17:39,640 to some folks based on, like you said, 480 00:17:39,640 --> 00:17:41,579 data sovereignty, data residency, 481 00:17:41,960 --> 00:17:42,460 GDPR, 482 00:17:43,559 --> 00:17:46,375 various legal requirements, things like that that that 483 00:17:46,375 --> 00:17:47,755 are out there. And 484 00:17:48,214 --> 00:17:51,035 you asked, like, where are the chats 485 00:17:51,414 --> 00:17:53,035 stored? I have no idea. 486 00:17:53,815 --> 00:17:55,654 I would hope that they're stored in the 487 00:17:55,654 --> 00:17:58,055 same place as, like, my, like, grounded memory 488 00:17:58,055 --> 00:17:59,914 for, like, my m three sixty five chats. 489 00:17:59,974 --> 00:18:01,539 But when is that? I I don't know. 490 00:18:01,539 --> 00:18:03,460 Like, that chat that crashed for me, and 491 00:18:03,460 --> 00:18:04,980 it just happened to be I I was 492 00:18:04,980 --> 00:18:06,580 in there prompt in a way and firing 493 00:18:06,580 --> 00:18:09,299 off requests, like, just when that anthropic API 494 00:18:09,299 --> 00:18:11,299 went down. That that thing, like I said, 495 00:18:11,299 --> 00:18:13,380 I can still get to the files because 496 00:18:13,380 --> 00:18:15,220 they're in my OneDrive. I can see the 497 00:18:15,220 --> 00:18:17,434 session ID and, like, I can map back 498 00:18:17,434 --> 00:18:18,795 to the GUID and the day and the 499 00:18:18,795 --> 00:18:19,295 time 500 00:18:19,674 --> 00:18:22,315 when that thing happened. So that's good. Like, 501 00:18:22,315 --> 00:18:24,234 the file storage is still there. I lost 502 00:18:24,234 --> 00:18:25,755 all the chat history. I've I have no 503 00:18:25,755 --> 00:18:28,474 idea where that is and what that looks 504 00:18:28,474 --> 00:18:30,789 like, along the way. So there is a 505 00:18:30,789 --> 00:18:32,869 little bit in the docs around, like, how 506 00:18:32,869 --> 00:18:34,250 does Cowork handle 507 00:18:34,630 --> 00:18:36,170 data. So authentication, 508 00:18:36,630 --> 00:18:38,710 super easy. Right? That's just your m three 509 00:18:38,710 --> 00:18:41,349 sixty five credentials and your org ID. Tenant 510 00:18:41,349 --> 00:18:41,849 isolation, 511 00:18:42,150 --> 00:18:43,369 so you can only 512 00:18:43,875 --> 00:18:46,914 work with data within your organization's tenant. Easy 513 00:18:46,914 --> 00:18:47,414 enough, 514 00:18:47,875 --> 00:18:49,255 because you can't access data 515 00:18:49,555 --> 00:18:51,795 cross tenant. And because you can only work 516 00:18:51,795 --> 00:18:54,275 with cloud data, like data in SharePoint or 517 00:18:54,275 --> 00:18:56,195 OneDrive, well, that that kinda takes care of 518 00:18:56,195 --> 00:18:57,474 it because you don't have to worry about 519 00:18:57,474 --> 00:18:59,339 the local access thing or anything like that. 520 00:18:59,339 --> 00:19:00,859 And if you did upload some data to 521 00:19:00,859 --> 00:19:02,460 the chat, it would get uploaded to your 522 00:19:02,460 --> 00:19:04,460 OneDrive and be part of the the session 523 00:19:04,460 --> 00:19:06,940 and all that. So file storage taken care 524 00:19:06,940 --> 00:19:08,859 of. You you're you're in OneDrive or SharePoint 525 00:19:08,859 --> 00:19:10,859 within your tenant. What's not clear is there's 526 00:19:10,859 --> 00:19:12,380 a little bullet when you go into the 527 00:19:12,380 --> 00:19:14,805 co work docs that says data subject rights. 528 00:19:15,045 --> 00:19:15,785 Access deletion, 529 00:19:16,325 --> 00:19:20,105 rectification, and portability requests are supported in accordance 530 00:19:20,164 --> 00:19:22,664 with Microsoft's privacy standards. 531 00:19:22,965 --> 00:19:25,445 Okay. So I would imagine that's, hey. I 532 00:19:25,445 --> 00:19:26,965 went into the m three sixty five admin 533 00:19:26,965 --> 00:19:29,605 portal and I clicked yes. Users within geo 534 00:19:29,605 --> 00:19:32,579 x y zed can get access to anthropic 535 00:19:32,640 --> 00:19:34,559 models, and then it's just off to the 536 00:19:34,559 --> 00:19:36,480 races from there. So, Scott, while you were 537 00:19:36,480 --> 00:19:39,039 talking, I just did a fascinating test on 538 00:19:39,039 --> 00:19:41,119 Copilot in my environment. Oh, you just asked 539 00:19:41,119 --> 00:19:42,319 it just to see if you could get 540 00:19:42,319 --> 00:19:43,299 it to leak again? 541 00:19:44,164 --> 00:19:45,924 No. We're not talking about what I got 542 00:19:45,924 --> 00:19:47,625 it to leak before. That's 543 00:19:48,724 --> 00:19:50,164 secret. If you run into me at a 544 00:19:50,164 --> 00:19:52,505 conference, come ask me. I am not recording 545 00:19:52,644 --> 00:19:53,865 when I got it to leak. 546 00:19:54,244 --> 00:19:55,924 I went into cowork. So I have a 547 00:19:55,924 --> 00:19:58,269 document in my environment. Let me preface this. 548 00:19:58,269 --> 00:20:00,190 I will more than happily give you these 549 00:20:00,190 --> 00:20:01,549 screenshots too if we wanna put them in 550 00:20:01,549 --> 00:20:03,549 the show notes. I have a document in 551 00:20:03,549 --> 00:20:05,549 my environment that I put a sensitivity label 552 00:20:05,549 --> 00:20:07,390 on. Mhmm. I did not encrypt it, so 553 00:20:07,390 --> 00:20:09,630 it's not using AIP or MIP or any 554 00:20:09,630 --> 00:20:12,609 of those, just a sensitivity label that's for 555 00:20:13,065 --> 00:20:14,044 labeling purposes. 556 00:20:14,424 --> 00:20:16,204 And then in my DLP policies, 557 00:20:16,585 --> 00:20:17,085 I 558 00:20:17,464 --> 00:20:18,524 put a policy 559 00:20:18,904 --> 00:20:21,005 or a Copilot and Copilot chat 560 00:20:21,544 --> 00:20:22,044 blocking 561 00:20:22,585 --> 00:20:23,085 Copilot 562 00:20:23,544 --> 00:20:24,044 from 563 00:20:24,424 --> 00:20:27,164 essentially accessing the content in this document 564 00:20:27,559 --> 00:20:30,039 or doing anything with the document. So it's 565 00:20:30,039 --> 00:20:32,200 just a simple test document. Like, in it, 566 00:20:32,200 --> 00:20:33,559 I wrote the color of the chair is 567 00:20:33,559 --> 00:20:34,059 blue, 568 00:20:34,359 --> 00:20:36,119 the color of the ocean is red, or 569 00:20:36,119 --> 00:20:39,160 something just something goofy like that. So if 570 00:20:39,160 --> 00:20:42,475 I go into Copilot chat, just normal Copilot 571 00:20:42,615 --> 00:20:44,775 chat session, make sure I'm on the work 572 00:20:44,775 --> 00:20:46,634 tab so I can get to my data, 573 00:20:46,775 --> 00:20:48,934 and I just do a slash command DLP 574 00:20:48,934 --> 00:20:50,775 policy test doc, what color is the chair 575 00:20:50,775 --> 00:20:53,095 based on this file, and Copilot returns to 576 00:20:53,095 --> 00:20:55,755 me, I attempted to open DLP policy test, 577 00:20:55,880 --> 00:20:57,480 but the content is blocked due to your 578 00:20:57,480 --> 00:20:59,660 organization's data loss prevention policies. 579 00:21:00,039 --> 00:21:01,720 Because of that, I don't have any visibility 580 00:21:01,720 --> 00:21:04,200 into the file's content, can't determine the color 581 00:21:04,200 --> 00:21:05,880 of the chair, blah blah blah blah blah 582 00:21:05,880 --> 00:21:08,220 blah blah. So works just like it intended. 583 00:21:08,535 --> 00:21:10,414 I did I wasn't paying attention. I had 584 00:21:10,414 --> 00:21:11,734 it on the web chat for a little 585 00:21:11,734 --> 00:21:13,414 bit too. I can still do a slash 586 00:21:13,414 --> 00:21:15,674 command and reference the document. And 587 00:21:15,975 --> 00:21:18,134 I asked it the same thing, and it 588 00:21:18,134 --> 00:21:20,055 just said it can't determine the color of 589 00:21:20,055 --> 00:21:23,059 the chair because there's no image content associated 590 00:21:23,059 --> 00:21:25,160 with it. It's text only, no description. 591 00:21:25,539 --> 00:21:27,539 I guess it kinda makes sense. It must 592 00:21:27,539 --> 00:21:30,279 be the difference that a web Copilot chat, 593 00:21:30,339 --> 00:21:32,660 how it interacts with the document versus on 594 00:21:32,660 --> 00:21:35,220 the work tab. Interesting that it didn't reference 595 00:21:35,220 --> 00:21:37,539 the DLP policy even though I added the 596 00:21:37,539 --> 00:21:39,835 document to the chat, but it still couldn't 597 00:21:39,835 --> 00:21:42,174 get to it. Then I went into Cowork 598 00:21:42,554 --> 00:21:45,115 and did the same thing. DLP policy, test 599 00:21:45,115 --> 00:21:46,554 doc, what is the color of the chair 600 00:21:46,554 --> 00:21:48,634 based on the file? Based on the document, 601 00:21:48,634 --> 00:21:50,335 the chair is blue. Cowork 602 00:21:50,714 --> 00:21:52,015 does not respect 603 00:21:52,660 --> 00:21:55,460 Copilot DLP policies. You turn this stuff on. 604 00:21:55,460 --> 00:21:56,599 You you use it. 605 00:21:57,299 --> 00:22:00,200 User discretion is advised. Yeah. And if you 606 00:22:00,500 --> 00:22:03,140 are doing DLP policies, you may want to 607 00:22:03,779 --> 00:22:06,019 and I get, like, Cowork's still frontier. Right? 608 00:22:06,019 --> 00:22:06,920 It still preview 609 00:22:07,474 --> 00:22:09,255 all the normal stuff, but 610 00:22:09,714 --> 00:22:11,894 CoWork at this point in time 611 00:22:12,195 --> 00:22:13,414 does bypass 612 00:22:14,515 --> 00:22:15,335 some of those 613 00:22:15,955 --> 00:22:18,934 security features that, I guess, I feel like 614 00:22:19,394 --> 00:22:19,974 by default, 615 00:22:20,355 --> 00:22:22,829 it would have been on that 616 00:22:23,210 --> 00:22:25,289 if we're gonna if I'm gonna go in 617 00:22:25,289 --> 00:22:28,890 and configure sensitivity labels and security and exclude 618 00:22:28,890 --> 00:22:30,109 certain things from Copilot, 619 00:22:30,490 --> 00:22:32,730 that it wouldn't be able to bypass it 620 00:22:32,730 --> 00:22:34,490 in that type of scenario. Maybe it gives 621 00:22:34,490 --> 00:22:36,704 a little credence to the do use things. 622 00:22:36,704 --> 00:22:37,904 Like, like, I can tell you, if you 623 00:22:37,904 --> 00:22:40,085 use MIP and it's encrypted, it's like, 624 00:22:40,545 --> 00:22:42,464 you're not get you're not getting that thing. 625 00:22:42,464 --> 00:22:44,944 You're safe there. I will say you're safe 626 00:22:44,944 --> 00:22:46,224 ish there. Like, you're 627 00:22:47,105 --> 00:22:49,345 as a user, there's still things that you 628 00:22:49,345 --> 00:22:51,099 can potentially do. So 629 00:22:51,400 --> 00:22:53,640 so for example, like, you can copy and 630 00:22:53,640 --> 00:22:55,960 paste data out of a a Word document. 631 00:22:55,960 --> 00:22:56,460 Right? 632 00:22:56,839 --> 00:22:58,059 And LLMs 633 00:22:58,440 --> 00:22:59,259 speak markdown. 634 00:22:59,799 --> 00:23:02,619 So while I was looking to see, 635 00:23:02,920 --> 00:23:04,279 okay, is there a way that I, like, 636 00:23:04,279 --> 00:23:05,720 I can make all this stuff work? I'm 637 00:23:05,720 --> 00:23:08,734 trying to, like, Google Bing, DuckDuckGo my way 638 00:23:08,734 --> 00:23:10,255 through life and see if I can figure 639 00:23:10,255 --> 00:23:12,815 this out. I did see some articles out 640 00:23:12,815 --> 00:23:16,115 there from folks who were talking about kinda 641 00:23:16,414 --> 00:23:18,894 markdown as the language of LLMs, which is 642 00:23:18,894 --> 00:23:21,859 true. And there's all these, like, just open 643 00:23:21,920 --> 00:23:23,140 websites that 644 00:23:23,440 --> 00:23:24,019 have fancy 645 00:23:24,400 --> 00:23:27,779 JavaScript engines, or there's a really nifty extension 646 00:23:27,839 --> 00:23:30,660 for Versus Code, which does paste as markdown. 647 00:23:31,200 --> 00:23:33,744 So you can copy your Word doc, just 648 00:23:33,744 --> 00:23:35,984 control c, give me all this content, and 649 00:23:35,984 --> 00:23:37,505 you can go and paste it into a 650 00:23:37,505 --> 00:23:40,224 markdown file. And then it's just out in 651 00:23:40,224 --> 00:23:40,804 the wild. 652 00:23:41,904 --> 00:23:45,184 Mark markdown's not getting a sensitivity label and 653 00:23:45,184 --> 00:23:47,505 IRM'd and all that stuff. So And all 654 00:23:47,505 --> 00:23:48,644 those. That's another 655 00:23:49,109 --> 00:23:51,029 thing I think that maybe, like, folks gotta 656 00:23:51,029 --> 00:23:54,009 think about. Like, it it's really just exciting, 657 00:23:54,309 --> 00:23:54,809 scary, 658 00:23:55,109 --> 00:23:55,609 interesting 659 00:23:55,990 --> 00:23:56,490 to 660 00:23:57,029 --> 00:23:59,190 kinda see the evolution of these things and 661 00:23:59,190 --> 00:24:00,250 see where the gaps 662 00:24:00,630 --> 00:24:03,450 and things come up all along the way. 663 00:24:03,734 --> 00:24:06,055 Like, I I don't envy, like, because I'm 664 00:24:06,055 --> 00:24:07,355 talking through these situations. 665 00:24:07,734 --> 00:24:09,194 Like, I don't envy, like, 666 00:24:09,494 --> 00:24:12,454 CSOs or things like that or chief information 667 00:24:12,454 --> 00:24:14,934 officers having to or legal. Right? Like, trying 668 00:24:14,934 --> 00:24:16,789 to figure out, hey, what do we do 669 00:24:16,789 --> 00:24:17,690 in our organization 670 00:24:17,990 --> 00:24:18,890 when it comes 671 00:24:19,349 --> 00:24:20,569 to the use of 672 00:24:20,869 --> 00:24:24,390 these models and these systems and contracting with 673 00:24:24,390 --> 00:24:26,630 these various vendors and things that are out 674 00:24:26,630 --> 00:24:29,375 there? Because in a world of just anything 675 00:24:29,375 --> 00:24:31,154 can be converted to raw text, 676 00:24:31,534 --> 00:24:32,034 then 677 00:24:32,654 --> 00:24:34,815 you you can just egress it and have 678 00:24:34,815 --> 00:24:37,134 it out there kinda thing. And so, like, 679 00:24:37,134 --> 00:24:39,054 I was playing around with that paste to 680 00:24:39,054 --> 00:24:41,909 markdown extension of Versus Code. Super cool, like 681 00:24:41,909 --> 00:24:44,149 I said, but you can do things like 682 00:24:44,149 --> 00:24:46,169 you can paste, say like an image 683 00:24:46,470 --> 00:24:49,190 from a website or from a document, and 684 00:24:49,190 --> 00:24:51,529 when you paste it in, it gets pasted 685 00:24:51,829 --> 00:24:54,869 as a base 64 encoded just native image 686 00:24:54,869 --> 00:24:56,785 in there. So it it's not even like, 687 00:24:56,785 --> 00:24:58,384 if you had, like, sensitive data in a 688 00:24:58,384 --> 00:25:00,785 flowchart or something like that coming through, you 689 00:25:00,785 --> 00:25:02,945 could potentially leak that into an LLM or 690 00:25:02,945 --> 00:25:05,105 something like that. So def definitely some stuff 691 00:25:05,105 --> 00:25:06,164 to think about. Yeah. 692 00:25:11,740 --> 00:25:13,980 This episode is brought to you by Trusted 693 00:25:13,980 --> 00:25:17,019 Tech. If you're managing Microsoft three sixty five, 694 00:25:17,019 --> 00:25:19,359 you already know licensing isn't simple. 695 00:25:19,740 --> 00:25:21,740 E three versus e five, the brand new 696 00:25:21,740 --> 00:25:25,144 e seven licenses, Copilot security bundles, and with 697 00:25:25,144 --> 00:25:28,024 price changes coming in July 2026, 698 00:25:28,024 --> 00:25:30,825 the stakes are getting higher. Trusted Tech helps 699 00:25:30,825 --> 00:25:33,384 IT leaders make sense of their Microsoft three 700 00:25:33,384 --> 00:25:36,279 sixty five environment with a free licensing consultation. 701 00:25:36,740 --> 00:25:37,480 Their engineers 702 00:25:37,779 --> 00:25:40,019 analyze what you're licensed for and what you're 703 00:25:40,019 --> 00:25:42,980 actually using and where you can optimize, whether 704 00:25:42,980 --> 00:25:44,200 that means consolidating 705 00:25:44,500 --> 00:25:48,039 security tools, preparing for Copilot, or eliminating wasted 706 00:25:48,099 --> 00:25:48,599 spend. 707 00:25:48,900 --> 00:25:52,755 Plus, they offer proactive and reactive support, which 708 00:25:52,755 --> 00:25:55,575 has been awarded yet another solution partner designation 709 00:25:55,795 --> 00:25:56,295 from 710 00:25:56,674 --> 00:25:58,615 Microsoft for support services. 711 00:25:58,994 --> 00:26:01,414 If you want a clear, data backed plan 712 00:26:01,555 --> 00:26:03,815 that has helped over 7,500 713 00:26:04,090 --> 00:26:06,990 subscribing customers save up to 20% on Microsoft 714 00:26:07,130 --> 00:26:10,350 three sixty five before your next renewal, visit 715 00:26:10,410 --> 00:26:16,990 trustedtech.team/mscloudprom365 716 00:26:17,049 --> 00:26:17,444 and schedule 717 00:26:18,404 --> 00:26:19,865 free consultation today. 718 00:26:24,724 --> 00:26:26,565 I was playing around with this a little 719 00:26:26,565 --> 00:26:28,244 bit more. Like, if I use the Claude 720 00:26:28,244 --> 00:26:32,419 model like Opus in chat, DLP works. I 721 00:26:32,419 --> 00:26:35,059 just tried it with another agent that I 722 00:26:35,059 --> 00:26:37,079 built that uses, like, WorkIQ 723 00:26:37,619 --> 00:26:38,119 and 724 00:26:38,500 --> 00:26:40,519 all the different m three sixty five ones. 725 00:26:40,740 --> 00:26:41,960 And that one, 726 00:26:42,259 --> 00:26:44,099 it does pick up that the file has 727 00:26:44,099 --> 00:26:46,285 a sensitivity label on it, and it says 728 00:26:46,285 --> 00:26:47,505 access to the files 729 00:26:47,805 --> 00:26:48,305 with 730 00:26:48,684 --> 00:26:50,144 the sensitivity label 731 00:26:50,525 --> 00:26:52,224 will be as per org policy. 732 00:26:52,684 --> 00:26:54,785 So it doesn't look like it's necessarily 733 00:26:56,365 --> 00:26:58,625 even tied to agents or 734 00:26:59,019 --> 00:27:01,500 the specific model because this agent I did 735 00:27:01,500 --> 00:27:03,500 set to use, I think it was Claude 736 00:27:03,500 --> 00:27:04,960 4.6. 737 00:27:05,339 --> 00:27:07,839 It does look to be very 738 00:27:08,220 --> 00:27:09,359 at least a DLP 739 00:27:09,660 --> 00:27:10,160 policy 740 00:27:10,859 --> 00:27:11,359 workaround 741 00:27:11,740 --> 00:27:13,759 does appear to be something 742 00:27:14,355 --> 00:27:15,095 cowork specific 743 00:27:16,115 --> 00:27:16,934 and not 744 00:27:17,234 --> 00:27:17,734 necessarily 745 00:27:18,194 --> 00:27:19,255 agent or 746 00:27:19,714 --> 00:27:21,714 model based. Now we don't know how the 747 00:27:21,714 --> 00:27:23,255 data necessarily flows 748 00:27:23,954 --> 00:27:24,454 to 749 00:27:25,075 --> 00:27:27,875 Claude and the cowork agent versus an agent 750 00:27:27,875 --> 00:27:29,095 I built versus 751 00:27:29,700 --> 00:27:32,179 Opus in a Copilot chat. I don't know. 752 00:27:32,179 --> 00:27:33,700 I think it gets to some of what 753 00:27:33,700 --> 00:27:35,319 we've talked about before is 754 00:27:35,619 --> 00:27:38,259 Copilot feels overly complex, I guess, when it 755 00:27:38,259 --> 00:27:39,940 comes to some of this stuff. Like, this 756 00:27:39,940 --> 00:27:42,819 feels like something I shouldn't have to be 757 00:27:43,244 --> 00:27:46,464 I shouldn't have to have five different ways 758 00:27:46,845 --> 00:27:49,105 to five different places I have to validate 759 00:27:49,244 --> 00:27:51,484 that my sensitivity labels work. Like, if I 760 00:27:51,484 --> 00:27:53,744 say this is excluded from Copilot, 761 00:27:54,045 --> 00:27:55,265 it shouldn't matter 762 00:27:55,640 --> 00:27:57,900 what I'm doing in Copilot. It should be 763 00:27:57,960 --> 00:28:00,039 uniform across the entire platform. We could go 764 00:28:00,039 --> 00:28:01,720 down this rabbit hole for a long time. 765 00:28:01,720 --> 00:28:03,799 Right? So think about we've talked in the 766 00:28:03,799 --> 00:28:06,759 past about, like, declarative agents. So great. Super 767 00:28:06,759 --> 00:28:08,545 easy to spin up. I wanna give this 768 00:28:08,545 --> 00:28:11,505 thing a description. There's also going down the 769 00:28:11,505 --> 00:28:14,625 path of, like, full foundry agent that you 770 00:28:14,625 --> 00:28:17,265 can, like, publish as a native agent out 771 00:28:17,265 --> 00:28:20,065 to Copilot and to Teams and all those 772 00:28:20,065 --> 00:28:22,200 other kinds of things that are out there. 773 00:28:22,200 --> 00:28:24,919 So that's another interesting scenario because now I'm 774 00:28:24,919 --> 00:28:26,839 not, like, in a declarative agent. I'm in 775 00:28:26,839 --> 00:28:29,720 an agent that sits over in Foundry, which 776 00:28:29,720 --> 00:28:32,380 is in Azure land. Sure. Still still within 777 00:28:32,440 --> 00:28:35,099 the boundary of my tenant for identity and 778 00:28:35,480 --> 00:28:37,634 all that kind of stuff, but not necessarily 779 00:28:37,694 --> 00:28:39,535 within the boundary of my tenant as far 780 00:28:39,535 --> 00:28:42,275 as, like, m three sixty five is hosted 781 00:28:42,414 --> 00:28:44,894 and not, like like it's not Azure. It's 782 00:28:44,894 --> 00:28:46,595 m three sixty five and Azure 783 00:28:46,894 --> 00:28:48,414 kind of thing. So you can also kinda 784 00:28:48,414 --> 00:28:50,130 have, like, that just 785 00:28:51,170 --> 00:28:53,089 have to think through, like like, alright. What 786 00:28:53,089 --> 00:28:55,890 does that mean? And, like I said, it's 787 00:28:55,890 --> 00:28:57,970 not I and maybe it's me. And I 788 00:28:57,970 --> 00:28:59,250 totally they get this could be a me 789 00:28:59,250 --> 00:29:00,529 thing, but I also think it's a little 790 00:29:00,529 --> 00:29:01,970 bit of, like, a Microsoft thing and just 791 00:29:01,970 --> 00:29:04,609 how it's presented, documented, pushed out there. Like, 792 00:29:04,609 --> 00:29:07,414 I spent a decent amount of time trying 793 00:29:07,414 --> 00:29:09,174 to go out and find and tell me, 794 00:29:09,174 --> 00:29:11,335 like, how some of this stuff works, where 795 00:29:11,335 --> 00:29:14,535 does sensitivity of labels lie, where does DLP 796 00:29:14,535 --> 00:29:17,894 apply, all these things. And it's not, like, 797 00:29:17,894 --> 00:29:19,679 well done, I guess. Like, you can go 798 00:29:19,679 --> 00:29:21,599 with, like, into the purview docs, like, for 799 00:29:21,599 --> 00:29:24,079 sensitivity labels, and it'll tell you, like, hey. 800 00:29:24,079 --> 00:29:27,380 This works with Copilot chat and Copilot agents. 801 00:29:27,599 --> 00:29:30,019 But is that true? Is that just Copilot 802 00:29:30,160 --> 00:29:33,634 declarative agents, or is that Copilot Foundry agents 803 00:29:33,634 --> 00:29:36,194 that then that agent in Foundry could have 804 00:29:36,194 --> 00:29:38,674 access to other tools? It could have, like, 805 00:29:38,674 --> 00:29:41,154 logic that potentially ships your data between different 806 00:29:41,154 --> 00:29:43,795 tools and has different integrations. Like, I don't 807 00:29:43,795 --> 00:29:46,369 know. The whole thing weaves in weird ways. 808 00:29:46,369 --> 00:29:46,869 So 809 00:29:47,410 --> 00:29:49,970 much like I'm, like, just delighted by, like, 810 00:29:49,970 --> 00:29:52,769 being back in terminals and CLI experiences and 811 00:29:52,769 --> 00:29:55,169 things like that, you can see all this 812 00:29:55,169 --> 00:29:56,230 potential there, 813 00:29:57,025 --> 00:29:59,424 but the rough edges, the friction, just the 814 00:29:59,424 --> 00:30:02,464 mental overhead, I think, for users, and I'll 815 00:30:02,464 --> 00:30:04,384 I'll totally admit, like, you and I are 816 00:30:04,384 --> 00:30:06,144 probably more on the advanced side where we're 817 00:30:06,144 --> 00:30:08,384 thinking about these things where most other people 818 00:30:08,384 --> 00:30:10,224 aren't. They're just hopping through life going like, 819 00:30:10,224 --> 00:30:12,789 oh, researcher, help desk, a new chat, word 820 00:30:12,789 --> 00:30:13,990 and web. I don't know the difference. So 821 00:30:13,990 --> 00:30:15,349 I was just start or work in web. 822 00:30:15,349 --> 00:30:16,630 I was just starting work, or I was 823 00:30:16,630 --> 00:30:18,470 just starting web. Oh, I didn't know you 824 00:30:18,470 --> 00:30:20,630 could select a model, any anything like that. 825 00:30:20,630 --> 00:30:23,029 So you've got that full spectrum too of, 826 00:30:23,269 --> 00:30:24,570 I I think just kinda 827 00:30:25,015 --> 00:30:26,234 personas and 828 00:30:26,535 --> 00:30:28,214 folks that are gonna be out there using 829 00:30:28,214 --> 00:30:28,875 these things. 830 00:30:29,174 --> 00:30:29,994 Wild times. 831 00:30:30,535 --> 00:30:32,615 We'll see. This will be interesting to keep 832 00:30:32,615 --> 00:30:34,535 coming back to, and I promise we'll get 833 00:30:34,535 --> 00:30:36,054 to our topic that we were gonna talk 834 00:30:36,054 --> 00:30:36,875 about eventually. 835 00:30:37,575 --> 00:30:39,419 Someday, we'll get there. We'll see. That that 836 00:30:39,419 --> 00:30:41,659 was a backup anyway, but thank thanks for 837 00:30:41,659 --> 00:30:43,500 letting me rant a little bit or at 838 00:30:43,500 --> 00:30:45,659 least do some follow-up on co work. No. 839 00:30:45,659 --> 00:30:47,019 I think it's how we all learn. Right? 840 00:30:47,019 --> 00:30:49,339 Like, some say, hope if one person out 841 00:30:49,339 --> 00:30:52,159 there listens to this and their takeaway is, 842 00:30:52,355 --> 00:30:53,714 I was thinking about playing with it, but 843 00:30:53,714 --> 00:30:55,315 maybe I'm gonna wait a couple weeks until 844 00:30:55,315 --> 00:30:57,154 it refines a little bit more. Maybe we 845 00:30:57,154 --> 00:30:58,914 save somebody else a a little bit of 846 00:30:58,914 --> 00:31:01,394 toil and overhead. Even you and I talking 847 00:31:01,394 --> 00:31:03,234 about it and starting to think through, again, 848 00:31:03,234 --> 00:31:05,880 like, the DLP policies and sensitivity labels, and 849 00:31:05,880 --> 00:31:08,460 I hadn't even thought about that before until 850 00:31:09,079 --> 00:31:11,000 you brought up that thing about it crashing 851 00:31:11,000 --> 00:31:13,480 and losing your session of where is this, 852 00:31:13,480 --> 00:31:15,900 and how is this looking at those. So 853 00:31:15,960 --> 00:31:17,559 appreciate it. If you come back and listen 854 00:31:17,559 --> 00:31:19,784 to this, here's your thing. Right? We'll dump 855 00:31:19,784 --> 00:31:22,044 the transcript out, throw this through an LLM, 856 00:31:22,345 --> 00:31:24,184 and have this just write your next m 857 00:31:24,184 --> 00:31:25,884 three sixty five Copilot 858 00:31:26,265 --> 00:31:30,025 whatever security workshop for you. Exactly. That's it, 859 00:31:30,025 --> 00:31:31,880 Scott. Podcast, we're gonna 860 00:31:32,259 --> 00:31:34,740 multipurpose this content. That's the plan. Right? I 861 00:31:34,740 --> 00:31:36,180 will let you go get to your weekend. 862 00:31:36,180 --> 00:31:37,460 I'm gonna go try to get a few 863 00:31:37,460 --> 00:31:39,380 more things done before my weekend, and my 864 00:31:39,380 --> 00:31:41,460 wife is standing outside the door texting me 865 00:31:41,460 --> 00:31:44,234 for my order for dinner. Alright. I'll let 866 00:31:44,234 --> 00:31:46,315 you go. Thanks as always, Ben. Appreciate it. 867 00:31:46,315 --> 00:31:47,755 Thanks, Scott. We'll talk to you later. Bye. 868 00:31:47,755 --> 00:31:48,494 Bye bye. 869 00:31:50,234 --> 00:31:52,555 If you enjoyed the podcast, go leave us 870 00:31:52,555 --> 00:31:54,795 a five star rating in iTunes. It helps 871 00:31:54,795 --> 00:31:56,474 to get the word out so more IT 872 00:31:56,474 --> 00:31:58,470 pros can learn about Office three sixty sixty 873 00:31:58,470 --> 00:31:59,210 five and Azure. 874 00:31:59,829 --> 00:32:01,509 If you have any questions you want us 875 00:32:01,509 --> 00:32:03,669 to address on the show, or feedback about 876 00:32:03,669 --> 00:32:05,990 the show, feel free to reach out via 877 00:32:05,990 --> 00:32:08,169 our website, Twitter, or Facebook. 878 00:32:08,470 --> 00:32:10,309 Thanks again for listening, and have a great 879 00:32:10,309 --> 00:32:10,809 day.

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Microsoft Cloud IT Pro Podcast

Ben Stegink, Scott Hoag

On the MS Cloud IT Pro Podcast, Scott and Ben discuss the Microsoft Cloud with a focus on IT Pros. They'll discuss the latest in Microsoft 365 and Office 365 News, Azure news and talk about their experiences with managing the Microsoft Cloud as well as interview industry experts on various cloud technology. They'll cover things such as SharePoint, Exchange, Microsoft Teams, PowerShell, Azure, Azure AD, Security, Networking, Storage, and the many other technologies and products that have made their way into the Microsoft 365 suite and Azure. To stay up-to-date on the latest in Microsoft Cloud news and gain some valuable knowledge as you deploy it within your own organization, make sure to tune in every week! Find out more at msclouditpropodcast.com.

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