Wednesday, October 12, 2022

Solved - Outlook Endlessly Asks for Password - Perhaps the biggest pain in my *ss solved!

 Outlook Requests Password Repeatedly - FIXED!

Some variation of this problem has plagued me on and off for years. I know you've seen it: Outlook asks for your password again and again and again . . . seemingly forever. But sometime, after ten or more attempts . . . it magically works. I've always thought that there were just layers of security that need to be verified. BUT, I know the one guiding rule of the 21st century: It's always DNS

So, I've solved a lot of these issues with troubleshooting of DNS and Autodiscovery, which is a 100% related to DNS.

But there are also layers of security added by O365 resellers, and all the servers between "the cloud" and your desktop. Somewhere along the line the right registry entries need to be in place to either ASK FOR or IGNORE certain levels of security.

Why? Well . . . Outlook relies, ultimately, on an active directory that used to be 100% onsite, and has morphed to the cloud. So the directory had evolved to emulate "onsite" requests in a hosted environment. And just to keep you guessing, that same AD is trying desperately to be compatible with a world that predates routing traffic from one LAN to another!!!

Bottom Line: O365 put the fuster in fuster-cluck!

(If you make a fortune selling t-shirts with that line, you owe me a beer.)

So . . . after step by painful step, I hope I have documented a process that will help you solve almost any occurrence of the annoying, frustrating, never-ending password request.

Feedback and improvements welcome.

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The Problem: Outlook (via O365) constantly asks for password, never connects.

A Proposed “Universal” Fix. Please execute each of these steps in order. When in doubt, reboot.


1.     Log the affected mailboxes


Email Address:                                                                       


Assigned Autodiscover:                                                         


2.     Verify that DNS is correct

a.     DNS Servers at registrar

b.     Autodiscover within DNS

c.     Ping


3.     Verify the problem

a.     Connect to affected machine [using whatever remote tool you commonly use]

b.     Open Outlook and verify that it requests password more than twice and never connects

c.     Use OWA or Webmail access to verify that the username/email/password combo are correct and work as expected.


4.     Verify Autodiscover registry entries

a.     Check out this article in case it’s interesting:

b.     Create this REG file: Autodiscoverfix.reg

                                               i.     Copy and paste this text exactly into Notepad or another text editor:


Windows Registry Editor Version 5.00











                                              ii.     Save the file as Autodiscoverfix.reg

                                             iii.     Run that file with administrative privileges
This may involve running CMD.exe with administrative privileges and then browsing to the appropriate folder and running it from the command line.

                                            iv.     Reboot and attempt to connect with Outlook.

If needed . . .


5.     Verify LSA registry entries (Local Security Authority)

a.     In Windows, click Start > Run. In the command box, type regedit and press enter

                                               i.     Navigate to HKEY_LOCAL_MACHINE\System\CurrentControlSet\Control\Lsa\

                                              ii.     Find the DisableDomainCreds entry. A value of 1 (enabled) will prevent you from saving new credentials
- If it doesn’t exist, create this DWord entry

                                             iii.     Change the value to 0 and reboot. You should now have the Add button available. Note that the value of 0 is the default value.

                                            iv.     Attempt to connect with Outlook.

If needed . . .


b.     Check the LmCompatibilityLevel entry.
Navigate to HKEY_LOCAL_MACHINE\System\CurrentControlSet\Control\Lsa\

                                    i.     It should be set to 3, which is the default value.
If you have another value, change it to 3.
If it does not work with 3, then change the value to 2 and retry.

                                   ii.     Reboot and attempt to connect with Outlook

If needed . . .


c.     Verify that your firewall or virus scanner/malware agent is not performing encrypted web scanning


Once you’re connected and things are fixed, you may notice that your Outlook is extremely slow. I’m not sure why this is, but it’s probably related to a database confused with different layers of security and connection information. To fix things up . . .

Create a new profile in Control Panel / Mail with the username, email, and password you just cleaned up. This will force the creation of a new OST file and should be much faster.

A few articles to make your life easier . . .

Troubleshooting Issues With Saving Outlook Password ( 

Why Can't I Connect My Outlook 2016/2019 To Exchange (

How to Fix It When Outlook Keeps Asking for a Password (

How To Fix The Credential Prompt Error In Outlook 2016/2019/O365 Desktop Client For Windows (

Please post your feedback, questions, and anything else that will help folks be rid of this pain in the neck. 


Tuesday, October 11, 2022

Revised Class - Automate Accounting with QuickBooks Online - Starts October 18th

Automate Your Accounting with QuickBooks Online and Integrated Apps

You’re guaranteed to learn something that will make or save you the price of admission!

Taught By: Rayanne Buchianico, coach and community builder

- Five Tuesdays - Oct 18th - Nov 15th

- All classes start a 9:00 AM Pacific

Register Now - Only $299*

QuickBooks is the defacto finance tool for small businesses - and that includes IT Service Providers. In this always-fresh course, Rayanne takes two tracks to improve your business: 1) Get the most out of QuickBooks Online, and 2) Take your business to the next level by connecting QBO to other tools and services.

This is a very hands-on course. As you follow along, you'll fix-up your current QBO configuration and get the most out of integrations with your PSA and other tools. Plus, you'll learn the most important reports to use, how to effectively (and securely) share sensitive financial data with clients, and generate beautiful and amazing reports.

Whether you're new or experienced at running a business, this course will take your practical financial education to the next level!

You will learn:

  • Touch your transactions exactly one time to avoid duplicated entries
  • Make your business audit-proof with automated attachments
  • Understand the purchasing and procurement process in detail
  • Connect your PSA for automated invoice importing
  • Pay your bills electronically from INSIDE QuickBooks Online
  • Match your vendor bills with actual credit or bank payments
  • Set up and record:
  • Deferred Revenue
  • Customer Deposits
  • Sales Tax
  • Hardware as a Service

and MORE!

ITSP University Certification:

Meets Certification Requirements for:

  • Management
  • Front Office

This class will be recorded. Each unit is generally posted within 24 hours of the live class. These recorded units will become the On-Demand class and you’ll have lifetime access to it.

Class Content

Unit 1 Introduction and Connecting Your PSA

Unit 2 Document Management and BillPay

Unit 3 Automating Accounts Receivable

Unit 4 Time, Payroll, and Revenue

Unit 5 Cash Flow and Putting It All Together

Register Now - Only $299*

Note: * Members of the Small Biz Thoughts Technology Community attend at no additional charge. See details in the Community


Monday, October 10, 2022

The ASCII Group Honors Solutions Granted with 2022 ASCII Cup

 I got this press release from my friends over at ASCII. Congratulations to the winners - and all the contenders!

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The ASCII Group Honors Solutions Granted with 2022 ASCII Cup

Bethesda, Maryland – October 10, 2022 – The ASCII Group, a large membership-based community of independent North American MSPs, MSSPs and Solution Providers, is pleased to announce the recipients of its annual ASCII Cup celebration, with awards presented to the ASCII Cup winner and Top 10 Vendors of 2022. This year, the Cup was awarded at the ASCII Success Summit on October 7 in Dallas, Texas.

For nearly 40 years The ASCII Group has provided programs, services, and resources for MSPs to better run their IT businesses. The ASCII Cup is a commemoration of the dedication that technology vendor partners deliver to ASCII membership. The awards are presented each fall to technology companies that are committed to innovation and channel goodwill in addition to helping ASCII members grow their IT businesses. The winners are voted upon by ASCII members at regional events. 

Each ASCII Success Summit in 2022 allowed attendees to vote for vendors in thirteen distinct categories: Best Overall Presentation; Best Partner Incentives; Best Education; Best Keynote Presentation; Most Innovative Solution; Best Market Opportunity; Best Partner Involvement; Best Rapid Pitch; Best Channel Program; Best Revenue Generator; Best Partner Support; Best New Solution; Best in Show.

The winners at each event are selected based on the total number of votes by the MSPs and solution providers in attendance; at the end of the Summits, the winner of The ASCII Cup is determined by tabulating the results of all submitted ballots.

The ASCII Group is pleased to celebrate the award recipients of this year's ASCII Cup:

The 2022 ASCII Cup Vendor of the Year – Solutions Granted

First Runner-Up – CyberGuard360

3rd Place – Pax8 

4th Place – SpearTip

5th Place – Mailprotector

6th Place – Huntress

7th Place – Gradient MSP

8th Place – ThreatLocker

9th Place – Datto

10th Place – Zomentum

“It has been a pleasure this year to work with so many technology vendors committed to moving the industry forward with channel-focused solutions for our MSP membership,” said Jessie Devine, Director of Channel Development at The ASCII Group. “We would like to congratulate Solutions Granted on winning the 2022 ASCII Cup as well as to recognize the Top 10 Vendors and companies that participated in our ASCII Success Summits. We applaud you for your innovation and commitment to our IT community.”

For more information, please visit

About The ASCII Group, Inc:

The ASCII Group is the premier community of North American MSPs, MSSPs and Solution Providers. The Group has members located throughout the U.S. and Canada, and membership encompasses everyone from credentialed MSPs serving the SMB community to multi-location solution providers with a national and international reach. Founded in 1984, ASCII provides services to members including leveraged purchasing programs, education and training, marketing assistance, extensive peer interaction and more. ASCII works with a vibrant ecosystem of leading and major technology vendors that complement the ASCII community and support the mission of helping MSPs to grow their businesses. For more information, please visit

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Saturday, October 08, 2022

Lots of Videos on Finding and Keeping Great Employees

 I am preparing for a webinar on the challenges of finding and keeping good talent in the current environment. Among other things, I did a search through the videos I've already created on the "HR" or hiring processes.

In case you haven't found it yet, I highly encourage you to take a look at my YouTube Channel:

Small Biz Thoughts.

I have almost 850 videos there, including hundreds on SOPs for IT consultants and managed service providers.

Here is a quick list of videos related to finding and keeping great employees. Most are five minutes or less. In all, there's more than four hours of material here. 

Please check these out. And as cliché as it sounds, please like and subscribe.

All feedback welcome!

How to Attract Stupendous Job Candidates

Basic Hiring Process

How to Address Mistakes


Salary vs Hourly

Tracking Time Hourly vs Salary

Comanage Employees and Clients

Effective Evaluations

Evaluations in the Big Picture

Goals and Evaluations

Employee Handbook

Employee Probation Period

Employees Looking for another Job

Hire vs Outsource

Why Hire Outsourced Techs?

Disloyal Employees

Employee Expenses

Employees with Tattoos

Firing or Laying Off Employees

Phone Rules In and Out of Office

Working with People We Like

Health and Retirement Benefits

"Nice" Benefits for Employees

Throwing Subcontractors Under the Bus

When to Give Pay Increases

Confidentiality and Non-Disclosure

Your First Hire - Part 1

Your First Hire - Part 2

Honesty in the Job Market

Technician Roles and Responsibilities

Front Office Responsibilities

Service Manager Roles and Responsibilities

How to Delegate Effectively

Three Rules of Successful Outsourcing

Email Rules for Technicians

Follow Your Own Rules

Dress Codes and Casual Friday

Culture - Every Company Has One

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I hope this is helpful. Please put comments here or below individual videos. I'm happy to engage in any discussions that evolve.