Category: Outlook SupportFor those folks who are willing to risk it and not upgrade their Windows 10 computers, here is a list of issues you could have. Some might be dealbreakers and some might have other band-aid options to get working. I’m not sure yet what will have problems so I’m risking it with you all. My main desktop is staying on Windows 10 with no option to upgrade to Windows 11. My other laptop has Windows 11 and I use it daily so I’m all set if something critical happens to my main desktop. I also have backed up all the data from the Windows 10 computer to an external hard drive, so it will be easier for me to set up a new Windows 11 computer. Btw…almost all of my daily use files are saved in my Business 365 OneDrive.
Issues you could experience:
If you need help help on this issue, please use the form below to get in contact
When you start up your new computer, it will have a start up wizard and that can take a few minutes to do. It will ask you during the set up wizard to log in with a Microsoft account or create a new one. I would go to the old computer and find out what account you logged into that computer with. It will make easier if you’re using OneDrive.
If you would like my help with a new PC set up, please use the form below. When I assist, this can be a 1-day job but I only bill for the time on the phone I’m helping you, so expect many phone calls and checking in between installations. I also know how to configure software quickly and solve errors fast, so if you have issues, they will be taken care of.
After the wizard has completed, you should run the updates. I would continue to check for new updates until done.
The rest of this list can be done in any order:
Then you can install your Office programs. If you need Outlook Classic you will need to download that as it does not come with 365 subscriptions anymore.
After Office is installed, then I set up Chrome, Adobe, Zoom Dropbox, Teams, Google drive, etc.
Finally, your data from the old computer. You can do this step at any time
Antivirus, Printers, VPN. I would save these for last due to the fact they can sometimes get in the way of the other installations
Outlook set up
Client called in with this issue and after some initial troubleshooting I determined it was Adobe. PDF’s printed fine with Preview App.
Give that a shot, I hope it helps!
Client with Microsoft 365 called me to help fix this issue. All of her records online (DNS) seemed to be ok, then I snooped around and could not find the exact error fix but some online Google matches pointed me to look at the SPF records and it pointed me to add this record: +include:_spf.google.com
I had her add that to her SPF record and she got it working again. She also found some others to add from her domain hosts FAQ.
Keep in mind that I always copy out any records before I update and edit. Measure twice, cut once. If something is wrong with your update, you can paste the old records back in.
If you need my help, use the form below.
| 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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