moderated Re: Gmail and Outlook: Recent Security Conundrums

Curtis Chong



I need more specifics before I can answer this question. I am gathering that Outlook Express is the email client being used—running on the Windows 7 operating system. This being the case, I would suggest two things to enable Outlook Express to work with the Gmail account.


  1. In the Google account itself, turn on two-factor authentication.
  2. Once this is done and verified, generate what Google calls an app-specific password. This is a string of letters and other symbols that are difficult to remember. Once you have obtained this generated password, re-establish the Gmail account in Outlook Express, using the generated password in place of the Google Account password, the latter still working when a person needs access to the account through a web browser.


If you want links or references to articles telling you how to do all of this, please feel free to reach out to me.


Best regards,


Curtis Chong



From: <> On Behalf Of Joseph Machise
Sent: Friday, June 10, 2022 5:44 PM
Subject: Re: Gmail and Outlook: Recent Security Conundrums


Curtis can you please tell me about windows7 tried turning it on and my google now even with out turning it on doesn't like the ports in outlook express, what can I do from Joseph, to make google work again 

----- Original Message -----

Sent: Friday, June 10, 2022 4:04 PM

Subject: Re: Gmail and Outlook: Recent Security Conundrums




If your version of Office is fairly new, you will not be required to turn on two-factor authentication. This is one reason why I, myself, am on the subscription version of Microsoft 365.




Curtis Chong



From: <> On Behalf Of Tom Behler
Sent: Friday, June 10, 2022 12:32 PM
Subject: Re: Gmail and Outlook: Recent Security Conundrums


Interestingly, I haven’t needed to make any changes here with Outlook and my g-mail account.


I don’t remember being asked for two-factor authentication, so hopefully, I’ll be prompted for that when the time comes.


Is there something I should be doing now?  I’m operating on the basis of the idea that “if it isn’t broken, don’t fix it!”.


Am using Microsoft 365 here on a Windows 10 PC.


Dr.  Tom Behler



From: <> On Behalf Of Curtis Chong
Sent: Friday, June 10, 2022 1:47 PM
Subject: Re: Gmail and Outlook: Recent Security Conundrums


You can’t anymore. Allow Less Secure Apps is no longer an available setting.


On Jun 10, 2022, at 11:44 AM, Sandra Streeter <sandrastreeter381@...> wrote:

How do you check whether you have “less secure apps” in operation?





Justice without force is powerless; force without justice is tyrannical.

(Blaise Pascal)


From: <> On Behalf Of Andy
Sent: Friday, June 10, 2022 1:26 PM
Subject: Re: Gmail and Outlook: Recent Security Conundrums


I had no issues with GMAIL on my iPhone, but did on the PC because I was using Outlook Express.




----- Original Message -----

From: aaron lane

Sent: Friday, June 10, 2022 9:08 AM

Subject: Re: Gmail and Outlook: Recent Security Conundrums


I've not had any issues yet with Thunderbird or my IPhone. I am following this thread, so I know what to do, just in case.



On 6/10/2022 10:50 AM, Brian Vogel wrote:

I have heard that it is not necessary to remove and re-create the Gmail account in all cases.  If you have previously been using the "less secure apps" method of accessing the account with email address and actual password, you can go in to your Google Account and generate an app specific password for Outlook and that email account.  Afterwards you update the account in outlook substituting the app specific password for your old text password.  As previously noted, you have to turn on two-factor authentication for the account.

Personally, I prefer to nuke the account and set it up again if IMAP access has been the access method being used.  Outlook 2016 and later walk you through doing the Gmail OAUTH steps and then everything is up to completely modern security protocols.

Outlook 2013 can be set up to use modern security protocols, too, but it requires the additon of 3 registry keys.  Why they never turned this feature on in an Outlook 2013 update I'll never know.  I have a REG script that sets these keys: Outlook2013ModernAuth.REG
Should you elect to download this, you will get a warning from Google that it cannot be virus scanned and is an executable that could harm your computer.  It's a text file containing registry edit commands to set those three keys, and after you download it, should you wish to examine it before running, select the file, bring up the context menu, and choose Edit.  Otherwise, if you select the file and activate it then this will fire up the regedit utility which will use the commands in this file to set the three keys.  When regedit fires up you will get a UAC dialog (if you have UAC on, and most do) asking if you want to allow changes to be made to your system, to which you must answer, Yes, if you want the registry keys to be added.

Brian - Windows 10, 64-Bit, Version 21H2, Build 19044  

Here is a test to find out whether your mission in life is complete.  If you’re alive, it isn’t.
     ~ Lauren Bacall

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