Mavericks certificate problems

I've been trying to remotely solve a problem my brother has been having with his iMac running 10.9.5 (getting through an OS version update remotely with him would be even more work).


App store says there are no compatible updates.


He's using the latest Chrome but also has the same trouble with Safari. About a third of the time he's getting the "Your connection is not private. Attackers might be trying to steal your information from [various websites]

NET::ERR:_CERT_DATE_INVALID" error.


His iMac's date/time are correct. I still had him go to the Date & Time and disable the "Set date and time automatically" checkbox, wait for 10 seconds, and then re-enable it. No help.


Browsing from an Incognito window (in Chrome) did not help.


I had him open the Keychain Access application and run Verify in Keychain First Aid. A few things related to his mail were found and fixed, but nothing else. I had him select System Roots and look for any times with the blue "plus" sign. Nothing.


What steps am I missing?


Posted on Oct 4, 2021 11:59 AM

Reply
Question marked as Top-ranking reply

Posted on Oct 4, 2021 1:09 PM

On the 30th September 2021 certificates expired causing older versions of browsers

such as Safari to report this error.


You can try downloading a valid certificate from here,

https://community.letsencrypt.org/t/os-x-10-11-clients-not-connecting-to-site-with-lets-encrypt-certificates/161576


It may be possible for you to upgrade the mac to a newer OS that can run more modern browsers.


The App Store Updates page only informs you of updates available for the OS you are running.


Installing a newer OS is called an upgrade.


Which OS you can upgrade to will be governed by which model and year your mac is.


Click on the  top left of your screen click on About This Mac to find out the year of your mac.


If you find your mac can upgrade to the newer OS's like macOS Mojave 10.14, macOS Catalina 10.15, 

or macOs Big Sur 11.6 I would recommend you upgrade to macOS High Sierra 10.13 first.


For High Sierra, Mojave or Catalina,


Open Safari and click on this link, 

How to get old versions of macOS – Apple Support

Go to Check Compatibility to see if your mac qualifies for the OS upgrade you want.

Then go to the Download OS section and click on the OS you want to install.


Before upgrading make a full back up of your Mac.


Check that third party apps you use have updates available for the new OS.

https://roaringapps.com

Check that your printers/ scanners etc have updated drivers and software available for the new OS.


Connect your mac to your router via cable rather than rely on WiFi.

Do not use your mac while it is downloading

and do not use any other devices that share the same internet connection.


If the App Store says ‘Open’ then it is detecting a previous download of the install app

go to the Applications folder locate Install macOS ******.app.

Move it to the Trash, empty the Trash.

Restart, click on the link again, the App Store should say ‘Get' or 'Download'.


If you want to or are able to install Big Sur, open Safari and click on the link below.

How to upgrade to macOS Big Sur - Apple Support


If you are considering upgrading to Catalina or Big Sur be warned they do not support 32bit apps.

Your Mac is probably running 32bit apps and these will need to be updated to 64bit apps,

some updates may be free, some may be paid. Use this free app to discover which apps you have

are 32bit, https://www.stclairsoft.com/Go64/ then contact the developers of the software to see

if they are offering 64bit updates.

Similar questions

4 replies
Question marked as Top-ranking reply

Oct 4, 2021 1:09 PM in response to Scott_R

On the 30th September 2021 certificates expired causing older versions of browsers

such as Safari to report this error.


You can try downloading a valid certificate from here,

https://community.letsencrypt.org/t/os-x-10-11-clients-not-connecting-to-site-with-lets-encrypt-certificates/161576


It may be possible for you to upgrade the mac to a newer OS that can run more modern browsers.


The App Store Updates page only informs you of updates available for the OS you are running.


Installing a newer OS is called an upgrade.


Which OS you can upgrade to will be governed by which model and year your mac is.


Click on the  top left of your screen click on About This Mac to find out the year of your mac.


If you find your mac can upgrade to the newer OS's like macOS Mojave 10.14, macOS Catalina 10.15, 

or macOs Big Sur 11.6 I would recommend you upgrade to macOS High Sierra 10.13 first.


For High Sierra, Mojave or Catalina,


Open Safari and click on this link, 

How to get old versions of macOS – Apple Support

Go to Check Compatibility to see if your mac qualifies for the OS upgrade you want.

Then go to the Download OS section and click on the OS you want to install.


Before upgrading make a full back up of your Mac.


Check that third party apps you use have updates available for the new OS.

https://roaringapps.com

Check that your printers/ scanners etc have updated drivers and software available for the new OS.


Connect your mac to your router via cable rather than rely on WiFi.

Do not use your mac while it is downloading

and do not use any other devices that share the same internet connection.


If the App Store says ‘Open’ then it is detecting a previous download of the install app

go to the Applications folder locate Install macOS ******.app.

Move it to the Trash, empty the Trash.

Restart, click on the link again, the App Store should say ‘Get' or 'Download'.


If you want to or are able to install Big Sur, open Safari and click on the link below.

How to upgrade to macOS Big Sur - Apple Support


If you are considering upgrading to Catalina or Big Sur be warned they do not support 32bit apps.

Your Mac is probably running 32bit apps and these will need to be updated to 64bit apps,

some updates may be free, some may be paid. Use this free app to discover which apps you have

are 32bit, https://www.stclairsoft.com/Go64/ then contact the developers of the software to see

if they are offering 64bit updates.

Oct 4, 2021 4:46 PM in response to Eau Rouge

Thanks, I was able to send him the security certificate (I tested the lencr.org website on an old, old Mac I had in the attic and ironically it couldn't open the website to download it so I got it for him). I guided him through the install and he's up and running.

He's had OS upgrade issues in the past--they keep failing--which is why he's stuck on 10.9, and I haven't been able to get there because of COVID to troubleshoot.

Oct 4, 2021 11:10 PM in response to Scott_R

Upgrading is usually straight forward.

What is causing the failures, any error messages.

What model and year is your brothers mac.

From that we can then determine what is the best OS for him to upgrade to.

Any mac that is running Mac OS X Mavericks 10.9.5 can upgrade to at least

Mac OS X El Capitan 10.11.6. Although he will still encounter the certificate issue

with that.

macs up to 2011 in general can upgrade to macOS High Sierra 10.13.6.

macs from 2012 can upgrade to macOS Mojave 10.14.6 or macOS Catalina 10.15.7.

And there may be a slim possibility he can upgrade to macOS Big Sur.

Go back to my original post for a guide to upgrading, perhaps you can share it with him.

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Mavericks certificate problems

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