Latest / Sidekick's What Just Shipped / HubSpot passkeys reach the Outlook add-in, with one catch | Shipped Aug 2026
Transcript
- Rob (AI host): You're between meetings, Outlook asks you to sign in to HubSpot again, and the password is on a sticky note. Dana (AI host): HubSpot now supports passkeys in its Sales Outlook add-in, so a fingerprint, face scan, or PIN can replace that password. Rob (AI host): Stick around for the one Outlook setup where passkeys still don't work, because it decides whether this helps you at all. Narrator (AI voice): This is Sidekick's What Just Shipped, presented by Sidekick Strategies. Narrator (AI voice): Your hosts, Rob and Dana, are AI. Narrator (AI voice): The voices are synthetic, the research is real, and humans check every claim before it reaches you. Rob (AI host): Quick disclosure: Dana and I are AI hosts. We don't have fingerprints. Rob (AI host): We're reading HubSpot's passkey help article, updated in late September 2026. Dana (AI host): Fair warning, today I'm playing an IT admin for a mid-sized sales team, someone who has reset more HubSpot passwords than anyone can count. Rob (AI host): Then this is your episode. Rob (AI host): HubSpot's August product updates say passkeys are now supported in the HubSpot Sales Outlook add-in, including devices where they previously weren't available. Dana (AI host): Back up. What is a passkey, in plain words? Rob (AI host): It's a login without a password. Rob (AI host): HubSpot's article says you confirm it with your device: biometrics like your face or fingerprint, a PIN code, or a password manager. Dana (AI host): Okay, but why is that safer than a strong password? Rob (AI host): HubSpot calls it phishing-resistant. Rob (AI host): A passkey is tied to the real HubSpot site, so it can't be reused on a fake login page. Rob (AI host): And it's inherently multi-factor: something you have, plus something you are. Dana (AI host): Huh, better pitch than mine. Dana (AI host): Who gets it? Is this an Enterprise perk? Rob (AI host): No. Rob (AI host): The passkey article is marked for all products and plans, and the August updates list passkey login for all Outlook add-in users. Dana (AI host): So how does a rep set one up? Rob (AI host): On desktop, in HubSpot. Rob (AI host): Click the settings icon in the top navigation bar, go to General, then Security, and click Set up passkeys. Rob (AI host): A prompt appears from your device, your browser, or your password manager. Rob (AI host): Confirm it, and the passkey shows in your settings. Dana (AI host): Can they do that in the mobile app instead? Plenty of reps never open a laptop. Rob (AI host): They can log in to the mobile app with a passkey, but they can't create one there. Rob (AI host): HubSpot says passkeys can only be set up on desktop. Dana (AI host): And for someone with a work laptop and a personal phone? Rob (AI host): Click Add another passkey. HubSpot notes each user can set one passkey per authenticator type. Dana (AI host): Here's my real question. Which Outlook are we talking about? Rob (AI host): Good catch, because HubSpot has two. Rob (AI host): The HubSpot Sales Office three-sixty-five add-in is for email accounts hosted by Microsoft, and it works with classic and new Outlook, on Windows, Mac, and the web. Dana (AI host): And the other one? Rob (AI host): The HubSpot Sales Outlook desktop add-in. Rob (AI host): It's in maintenance mode, so it's no longer being improved, and it only runs in classic Outlook for Windows. Rob (AI host): HubSpot's passkey article says passkey login is not available with that desktop add-in. Dana (AI host): Oh, there's the catch. Dana (AI host): So with the right add-in, what does signing in look like? Rob (AI host): On HubSpot's desktop login screen, you enter your email, click Next, then click Sign in with a Passkey and confirm with your fingerprint, PIN, or password manager. Rob (AI host): Here's a made-up example. Picture a hypothetical rep, Priya, with a Microsoft-hosted inbox. Rob (AI host): She opens the add-in, picks the passkey, touches her fingerprint reader, and she's back to logging emails. Rob (AI host): Her teammate on the old desktop add-in still types a password. Dana (AI host): And can the teammate just switch add-ins? Rob (AI host): Not always. HubSpot's install guide says the Office add-in needs an email account hosted by Microsoft. Rob (AI host): If your email is hosted somewhere else, the desktop add-in is the option, and that one only runs in classic Outlook for Windows. Dana (AI host): So step zero for me is finding out who's on which add-in, and why. Rob (AI host): Why it matters: a login that takes seconds is a login reps don't skip, so more email activity reaches the CRM. Dana (AI host): That's our research's angle too. Dana (AI host): The add-in is where many reps log activity without leaving their inbox. Rob (AI host): So who notices the difference first? Dana (AI host): Our research points to reps who live in Outlook every day, RevOps leaders who want cleaner activity data, and IT admins who want passwordless sign-in across HubSpot. George B. Thomas (AI voice clone): Hey, it's George B. Thomas from Sidekick Strategies. George B. Thomas (AI voice clone): Full honesty, this is my AI voice clone, made with my permission. George B. Thomas (AI voice clone): Login settings are just one of the things in a portal that nobody checks until something breaks. George B. Thomas (AI voice clone): Our free HubSpot Portal Audit asks targeted questions about the hubs you use, then scores your portal from zero to one hundred with severity ratings and your top three next steps. George B. Thomas (AI voice clone): It takes about five minutes, and we never need access to your account. George B. Thomas (AI voice clone): Look for it under tools at Sidekick Strategies dot com. Dana (AI host): Rob, what changed since our August write-up? Rob (AI host): Two corrections. Our write-up says every place you sign into HubSpot now supports passkeys. Rob (AI host): HubSpot's passkey article says passkey login is still not available with the Outlook desktop add-in. Rob (AI host): And it says passkeys complement single sign-on rather than replace it. Rob (AI host): HubSpot's article is stricter: if you're required to use single sign-on to log in, you aren't eligible to use passkeys. Dana (AI host): That second one matters to me. We require single sign-on for the sales team. Rob (AI host): Then, per HubSpot, this isn't for those users yet. Rob (AI host): One more thing we couldn't confirm: our write-up describes the exact add-in screens, including a separate browser window. Rob (AI host): We didn't find those steps on a HubSpot page, so treat them as unconfirmed until you try it. Dana (AI host): What if someone loses their phone, and the passkey with it? Rob (AI host): If two-factor authentication is set up, they click Try another method and log in with that. Rob (AI host): Otherwise they choose the Lost your passkey link and verify their identity. Rob (AI host): HubSpot warns account recovery can take forty-eight to seventy-two hours. Dana (AI host): Ouch, that's a long wait. Rob (AI host): And if the add-in keeps asking you to log in, HubSpot's troubleshooting page points to your account's session timeout length, which a Super Admin can change. Dana (AI host): Okay. Give me the plan, for an admin rolling this out. Rob (AI host): Step one: check which add-in each rep uses. Rob (AI host): The Office add-in can use passkeys; the desktop add-in can't. Dana (AI host): Step two: check who is required to use single sign-on, because those users can't use passkeys. Rob (AI host): Step three: have each rep set up a passkey on desktop, under General and Security, and add a second one for their other device. Dana (AI host): Step four: make sure two-factor authentication is on, so a lost passkey isn't a three-day lockout. Rob (AI host): Step five: once the team is set, a Super Admin can make passkeys an allowed login method, pick an enforcement date, and HubSpot emails the users affected. Dana (AI host): My verdict: turn it on for Office add-in users, but skip it for anyone stuck on single sign-on or the old desktop add-in. Rob (AI host): The habit to build: set up two passkeys, not one. Dana (AI host): All of our sources are linked in the show notes, with more research waiting at Sidekick Strategies dot com. Rob (AI host): Thanks for listening, and enjoy logging in faster. Dana (AI host): Touch the sensor, skip the sticky note. Narrator (AI voice): Sidekick's What Just Shipped is presented by Sidekick Strategies, with AI hosts Rob and Dana and AI-generated music. Narrator (AI voice): We're independent, and not affiliated with HubSpot. Find our research at Sidekick Strategies dot com.