Lisa Hendrickson is the owner of Call That Girl. She is an Outlook Expert and Microsoft 365 Consultant.
| Meeting summary for Outlook Classic vs. New O365: How to Avoid Brand-Trust Issues in the Changeover (07/03/2025) | |
| Quick recap
Lisa and Tanya hosted a webinar focused on the transition from Outlook Classic to the new Outlook, discussing the challenges and changes associated with the update, including migration processes and security measures. They covered the differences between various email systems and emphasized the importance of preparing for the upcoming changes, particularly the shift towards cloud-based migrations and the eventual decommissioning of classic Outlook. The conversation ended with discussions about the limitations of the new Outlook and the need for businesses to adapt to new technologies, while Tanya offered services and encouraged attendees to participate in future webinars. Next steps
Summary Outlook Brand Integrity Webinar Lisa and Tanya hosted a webinar about the new Outlook, focusing on brand integrity and client trust. They discussed the upcoming changes to Outlook and the potential impact on businesses. Lisa shared her extensive experience in the tech industry and her expertise in Outlook. Tanya introduced Lisa as the “Queen of Outlook” and highlighted her knowledge of the new Outlook. They planned to cover questions and answers after the presentation and offer a special back-to-basics session at the end. Outlook Transition and Migration Challenges Lisa discussed the transition from Outlook Classic to the new Outlook, highlighting disruptions faced by users on POP and IMAP accounts due to Microsoft’s forced updates. She explained that users might encounter a new Outlook version after a reboot, which could lead to data loss if not configured properly. Lisa recommended migrating to Exchange to avoid these issues and provided a link for users to download Outlook Classic if needed. She encouraged attendees to ask questions and offered assistance for those struggling with the transition. Exchange Migration and Email Systems Lisa explained the differences between POP, IMAP, and Exchange email systems, noting that Exchange offers full synchronization with calendars, contacts, and tasks, while POP and IMAP lack this functionality. She highlighted that Microsoft is gradually transitioning users to Exchange, with the new Outlook 2029 version removing customizable features and requiring a migration process. Lisa emphasized the importance of preparing for this transition by ensuring compatibility with Office 365 and third-party apps, and she mentioned her upcoming Patreon content to help users adapt to the changes. Outlook Migration: IMAP to Exchange Lisa explained the process of migrating from IMAP to Exchange, noting that users can test the new Outlook by toggling between versions without risk. She highlighted that Exchange users can access their calendar, contacts, and autocomplete features, while IMAP users need manual email and contact migration. Lisa also discussed the challenges of managing multiple email accounts and the need for contact cleanup to ensure seamless integration. She emphasized that while new Outlook lacks some classic features, such as plugins, companies are developing apps to integrate with the new version, and Microsoft plans to phase out classic Outlook by 2029. DNS and Email Delivery Best Practices Lisa discussed the importance of maintaining up-to-date DNS records, particularly DMARC and SPF, to ensure email delivery and brand trust. She explained how to check these records using tools like MX Toolbox and emphasized that issues with Yahoo, AOL, and Google email services are often beyond users’ control. Tanya shared her experience with deliverability issues when using GoDaddy’s federated Office 365 version, highlighting the limitations compared to a direct Microsoft subscription, and Lisa recommended migrating to a full-featured Office 365 plan to resolve these issues. Email Security and MFA Best Practices Lisa discussed security measures for email accounts, emphasizing the importance of having a “break glass” global administrative account for emergency access. She advised testing Multi-Factor Authentication (MFA) regularly and moving authentication apps to new devices to avoid disruptions. Lisa also highlighted the challenges of updating security settings in new Outlook and the increasing sophistication of hackers, who are now exploiting phone and cookie vulnerabilities. Outlook Transition and Data Migration Lisa discussed the transition from classic to new Outlook, noting that while new Outlook is less configurable, it breaks less frequently. She emphasized the importance of backing up Exchange data, recommending cloud-based solutions like Veeam or Cloud Alley for businesses, and exporting to PST files for individuals. Lisa also mentioned that classic Outlook will be decommissioned by 2029 or 2030, and she advised attendees to start preparing for this transition by using templates and exploring new features in Outlook 365. Outlook Migration and Knowledge Sharing Lisa discussed her experience with the new Outlook and her efforts to learn and share knowledge about it, including her upcoming book and resources. She explained that Carbonate and Cloud Alley are owned by the same company and shared insights from her past work with Cloud Alley. Lisa also mentioned conducting an onboarding assessment for clients and migrating some of them to Exchange, while preparing for the transition to the new Outlook. Tanya expressed gratitude for Lisa’s contributions and highlighted the supportive tech community. Outlook Update Challenges and Migration The meeting focused on the challenges and changes associated with the new Outlook update, including issues with PST file exports and calendar sync. Lisa and Tony discussed the limitations of the new Outlook, such as the inability to import PST files, and the potential impact on their businesses due to the shift towards cloud-based migrations. Tanya offered a brand audit service at a discounted rate and encouraged attendees to sign up for future webinars. The group also discussed the importance of email and communication for businesses and the need to adapt to new technologies. |
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I had a client call in today and his New Outlook setup with regular free gmail.com wasn’t updating new emails since yesterday. I was traveling so I could not remote in, I asked him to restart his computer and let me know if that helped. I got home and called him back and it didn’t change. I had him try the “sync” button. That failed too. So I remoted in and literallly just clicked on the inbox, then clicked on another folder and then his inbox started downloading new email.
Am I the New Outlook Whisperer? Maybe lol. Either way, not sure what was wrong here but that worked for him. My next move if that failed was to remove his gmail account, close New Outlook and add the account back in. He called in last week with an issue of his Gmail security pop ups and no email was coming in on two computers. I connected the accounts and it worked great after that. This was probably just a glitch.
If you need my help, fill out the form below. Happy to help!
Hopefully this post is helpful for you. New Outlook problems are now becoming calls into queue as so many people are using it. I’ll be posting my New Outlook articles as I come across fixes. You can see them all on the ride side bar of this page or go to https://callthatgirl.biz/new-outlook-resource-guide
How it was resolved: I give props when props are due, I didn’t have time on that call to figure it out, so I put in my research queue for the night. The client ended up doing some of his own research and did something I never thought would work, but he did a full (advanced repair) Office repair and that fixed it. So now I’m telling you all this, it might not work for you but it worked for him. I was thrilled to learn because we are all learning what fixes New Outlook together here.
If you need help use the form below. If you have something new going on, please reach out for sure. I am enjoying the New Outlook journey of errors and problems to solve.
Fill out the form below to get started, I’ll email you an invite to the Zoom meeting.
