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I'm struggling to login to App store or iTunes. I found several posts on this issue already:

Cannot Connect to the App Store

macOS: Cannot connect to app store

Cannot connect App Store after upgrading to Mavericks

When I open my Mac and select apple menu > app store I see a blank grey square:

enter image description here

When I try to log in by clicking store menu > sign in I receive an error message "connection failed".

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Then, when I try to open iTunes "The certificate for this server is invalid":

enter image description here

I followed the steps advised in several blog posts on this e.g. this one.

These steps include:

  1. Verifying I have internet connection via network settings window
  2. Set Macs DNS server to Googles with 8.8.8.8 and 8.8.4.4. Mine was set to this already. Restarted Mac. Problem persists.
  3. In finder, navigated to /var/db/crls/ and moved both cricache.db and ocspcache.db to the trash and then emptied the trash. Restarted Mac, problem persists.
  4. Looked for problem certificates in Keychain access under /Applications/Utilities/. "In the left pane, click on Certificates under Category. In the search field at the top right corner of the KeyChain Access window, type Class and press Return. Among the search results, locate and double-click on a certificate that has an icon with a blue outline. This will open a window with information pertaining to the certificate.". None of my certificates have a blue outline, everything appears in order here.

Other information: I don't know which version of Macos I have because when I navigate to the Apple menu > about this Mac all it says is Macbook OSX 10.9.5 (Mavericks?):

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I have an ssd drive. I don't know if that's relevant or important.

Exhaisted all Google searches, blogs and posts. I would like to install any available updates, login to iTunes and generally just use my Apple ID with my Mac.

Does anyone have a solution to this or hypothesis about what I can try next?

EDIT:

Some new information. From a comment I visited https://init.itunes.apple.com in Safari and then selected show certificates which resulted in this screen shot:

enter image description here

  • Hello Doug, welcome to Ask Different. Could it be you are behind an HTTPS proxy? Are you in a corporate environment or trying to access the App Store when connected to a VPN? Open System Preferences>Network>Advanced...>Proxies and check whether a proxy is configured in "Auto Proxy Discovery", "Automatic Proxy Configuration" or "Secure Web Proxy". Is any of them checked? – jaume Sep 29 '18 at 15:22
  • Hello @jaume. I navigated to that menu, no items were checked. I'm currently on my home wifi connection with a large local ISP. I have this issue at other locations too, I even tried to connect in various random cafes but with the same outcome :( – Doug Fir Sep 29 '18 at 15:26
  • Thanks for your comment, could you open Safari, go to init.itunes.apple.com, click the lock and press "Show Certificate"? I see a certificate issued by "DigiCert SHA2 Extended Validation Server CA" which expires on "Friday, August 30, 2019 at 2:00:00 PM Central European Summer Time" (if you are in a time zone different then CEST you'll obviously see another time). If I click the "Details" section, I see "Organization: Apple Inc." What do you see? If it differs from what I describe, could you add a screenshot to your question? – jaume Sep 29 '18 at 15:35
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    From extended discussion in chat, it looks like I might have a compromised machine with a certificate issues by an unexpected provider. Recommended course of action is to use Time Machine app to restore my Mac to a previous state and then revisit itunes.apple.com. Seeking a certificate issued from DigiCert and not Entrust.Net. – Doug Fir Sep 29 '18 at 16:19
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    OK let me make that an answer so I can be more specific. – Ruskes Sep 29 '18 at 17:31
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Your user profile on your Mac might be compromised.

To test, create new user and try to access iTunes or App Store.

If it works lets try repair your user profile with permissions repair.

Restoring the OSX from backup will not fix that, it will keep your user profile as is.

Just as safety and unexpected problems, create second Administrator (full access) account.

Launch Disk Utility, located at /Applications/Utilities/.
Select the 'First Aid' tab.
In the left-hand pane, select a volume you wish to run Repair Permissions on. ...
Click the 'Repair Disk Permissions' button.

Also see this article to restore/reset permissions

But your problem might be even deeper. The certificates reside in KeyChain.

Repairing keychain it might be tricky so follow the instructions carefully (like FIRST make BACKUP).

  • I created a new user admin profile and was able to access the App store with that profile. I then repaired disk permissions per your instructions and waited till the application confirmed this task was complete. I did this both in the new user profile and then in my original one. Back on the original user profile I am still unable to access App store or itunes and when I visit init.itunes.apple.com I receive the same certificate warning per my screen shot above. – Doug Fir Sep 29 '18 at 17:49
  • @DougFir so your user profile has a deeper problem, try this then support.apple.com/en-us/HT203538 – Ruskes Sep 29 '18 at 17:57
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    Success! Thank you! I followed that link and was able to subsequently repair my disk, restart and access the app store! Many thanks. When I now visit init.itunes.apple.com I see DigiCert as the issuer – Doug Fir Sep 29 '18 at 18:38
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    @DougFir you are most welcome, it makes my time spend here worth while helping people. Also thanks to your very detailed question. – Ruskes Sep 29 '18 at 18:41

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