8303465: KeyStore of type KeychainStore, provider Apple does not show all trusted certificates #13945

RealCLanger · 2023-05-11T21:38:35Z

With this PR we try to be better in loading certificates from the MacOS Keychain into a JDK Trust store.

The current implementation after JDK-8278449 would only load/trust certificates from an identity (with private key available) and certificates that have explicit trust set in the user domain (as shown by security dump-trust-settings). This, however is not sufficient and does not match the MacOS system behavior, e.g. if you compare with tools like curl or Safari.

This change does the following:

The native method that reads trust settings will call the API SecTrustSettingsCopyTrustSettings on a certificate for both, User and Admin domain.
We now trust self-signed certificates that have an explicit trust entry with no sub-records or no sub-records that would deny the certificate usage for any purpose.
The check for double aliases has been augmented by comparing whether the certificate to be added is the same as the one that is already present. This can happen if a certificate is contained in both, the user and the system keychain, for instance.

I have added a test that verifies whether certificates that should be trusted from "security dump-trust-settings" are contained in the keystore and those that should be disallowed are absent.

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Commit message must refer to an issue
Change requires CSR request JDK-8308690 to be approved

Issues

JDK-8303465: KeyStore of type KeychainStore, provider Apple does not show all trusted certificates
JDK-8308690: KeyStore of type KeychainStore, provider Apple does not show all trusted certificates (CSR)

Reviewers

Matthias Baesken (@MBaesken - Reviewer) ⚠️ Review applies to b14e5f2c
Weijun Wang (@wangweij - Reviewer)

Reviewing

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bridgekeeper · 2023-05-11T21:39:49Z

👋 Welcome back clanger! A progress list of the required criteria for merging this PR into master will be added to the body of your pull request. There are additional pull request commands available for use with this pull request.

openjdk · 2023-05-11T21:41:57Z

@RealCLanger The following label will be automatically applied to this pull request:

security

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mlbridge · 2023-05-11T21:51:56Z

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MBaesken · 2023-05-16T07:46:37Z

Hi Christoph, I do not see any reference to kSecTrustSettingsDomainSystem in your coding. Handling at least kSecTrustSettingsDomainUser and kSecTrustSettingsDomainAdmin is good but I am not sure about kSecTrustSettingsDomainSystem . Did you find some documentation why it should be omitted ?

MBaesken · 2023-05-16T09:10:24Z

Additionally, the return value of SecTrustSettingsCopyTrustSettings (https://developer.apple.com/documentation/security/1400261-sectrustsettingscopytrustsetting) should better be checked.

RealCLanger · 2023-05-17T07:14:06Z

Hi Christoph, I do not see any reference to kSecTrustSettingsDomainSystem in your coding. Handling at least kSecTrustSettingsDomainUser and kSecTrustSettingsDomainAdmin is good but I am not sure about kSecTrustSettingsDomainSystem . Did you find some documentation why it should be omitted ?

Hi Matthias,
yes, I think it is not nicely documented. I've seen in testing, that kSecTrustSettingsDomainSystem merely holds information for trusted root CAs. So in theory, we could add this. However, other code in that area that we've found out in the wild doesn't do it as well. Let's see what others think about this.

MBaesken · 2023-05-17T07:36:33Z

Hi Christoph, I do not see any reference to kSecTrustSettingsDomainSystem in your coding. Handling at least kSecTrustSettingsDomainUser and kSecTrustSettingsDomainAdmin is good but I am not sure about kSecTrustSettingsDomainSystem . Did you find some documentation why it should be omitted ?

Hi Matthias, yes, I think it is not nicely documented. I've seen in testing, that kSecTrustSettingsDomainSystem merely holds information for trusted root CAs. So in theory, we could add this. However, other code in that area that we've found out in the wild doesn't do it as well. Let's see what others think about this.

Yes this seems to be the case. Could you maybe add a one liner comment to libosxsecurity/KeystoreImpl.m (near to the user and admin domain handling) summarizing what you said? And I still prefer checking the return values of the calls to SecTrustSettingsCopyTrustSettings .

…view comments

RealCLanger · 2023-05-17T08:01:49Z

Yes this seems to be the case. Could you maybe add a one liner comment to libosxsecurity/KeystoreImpl.m (near to the user and admin domain handling) summarizing what you said? And I still prefer checking the return values of the calls to SecTrustSettingsCopyTrustSettings .

Done. 😄

MBaesken · 2023-05-17T12:42:32Z

src/java.base/macosx/native/libosxsecurity/KeystoreImpl.m

Regarding CFArrayGetValueAtIndex, when looking at other usages of the function in the codebase the result is NULL checked usually. Should we do this here too? I admit the old coding does not have it as well.

Hm, can it really be NULL? I mean before we check the array size and then iterate the valid range.

MBaesken

So please check the CFArrayGetValueAtIndex usage, but otherwise looks okay to me now, thanks for the adjustments.

openjdk · 2023-05-17T12:56:44Z

@RealCLanger This change now passes all automated pre-integration checks.

ℹ️ This project also has non-automated pre-integration requirements. Please see the file CONTRIBUTING.md for details.

After integration, the commit message for the final commit will be:

8303465: KeyStore of type KeychainStore, provider Apple does not show all trusted certificates

Reviewed-by: mbaesken, weijun

You can use pull request commands such as /summary, /contributor and /issue to adjust it as needed.

At the time when this comment was updated there had been 226 new commits pushed to the master branch:

ac1597b: 8309409: Update HttpInputStreamTest and BodyProcessorInputStreamTest to use hg.openjdk.org
fdb5893: 8309391: Remove non-failing tests from test/jdk/ProblemList-Virtual.txt
6edd786: 8309265: Serial: Remove the code related to GC overheap limit
61bb014: 8309254: Implement fast-path for ASCII-compatible CharsetEncoders on RISC-V
62c935d: 8308978: regression with a deadlock involving FollowReferences
aff9cea: 8303530: Redefine JAXP Configuration File
1bb037b: 8309329: com/sun/jdi/DeferredStepTest.java fails with virtual threads due to not waiting for threads to exit
a23bbea: 8309241: ClassForNameLeak fails intermittently as the class loader hasn't been unloaded
931913f: 8309200: java/net/httpclient/ExecutorShutdown fails intermittently, if connection closed during upgrade
dc21e8a: 8296411: AArch64: Accelerated Poly1305 intrinsics
... and 216 more: https://git.openjdk.org/jdk/compare/690d3969b80776bf896fbfbfac5eabe7d074c9bb...master

As there are no conflicts, your changes will automatically be rebased on top of these commits when integrating. If you prefer to avoid this automatic rebasing, please check the documentation for the /integrate command for further details.

➡️ To integrate this PR with the above commit message to the master branch, type /integrate in a new comment.

seanjmullan · 2023-05-17T17:34:42Z

Please don't integrate this until I or someone from my team reviews it. Thanks.

wangweij · 2023-05-17T20:49:34Z

No matter what SecTrustSettingsCopyTrustSettings returns, you will always call jm_createTrustedCertEntry. This means if I add a self-signed certificate but has not added any trusted settings onto it, it will be always trusted. Is this intended?

RealCLanger · 2023-05-17T21:10:49Z

Please don't integrate this until I or someone from my team reviews it. Thanks.

Sure.

RealCLanger · 2023-05-17T21:25:29Z

No matter what SecTrustSettingsCopyTrustSettings returns, you will always call jm_createTrustedCertEntry. This means if I add a self-signed certificate but has not added any trusted settings onto it, it will be always trusted. Is this intended?

Yes, I will call jm_createTrustedCertEntry for every certificate, at least independent from the results of the SecTrustSettingsCopyTrustSettings calls.

As I outlined in my initial PR description, point 3, the actual check whether a certificate is self-signed is done in the createTrustedCertEntry Java method. So, yes, when there is a self-signed certificate without explicit trust settings, it is always trusted. I thought that this was the intentional behavior even before my changes. However, the difference to the code before is that I look at the certificate and check whether it is a real plain self-signed certificate that can be used for TLS communication - which would be trusted. But what's not trusted now are CA root certificates which also means self-signed but additionally key usage 'keyCertSign' and/or 'cRLSign'. See this code

Makes sense?

wangweij · 2023-05-18T00:00:58Z

Before your new change, such a certificate is not trusted, because SecTrustSettingsCopyTrustSettings returns errSecItemNotFound so jm_createTrustedCertEntry is not called at all.

I am not sure if such a certificate is meant to be always trusted. Note that you can create such an entry with only security add-certificates but not security add-trusted-cert. macOS allows anyone to run the first command but prompts you for an administrator password when running the second. The name of the second command also implies that it's the only way to assign trust to a certificate, IMHO.

RealCLanger · 2023-05-19T09:13:08Z

Before your new change, such a certificate is not trusted, because SecTrustSettingsCopyTrustSettings returns errSecItemNotFound so jm_createTrustedCertEntry is not called at all.

I am not sure if such a certificate is meant to be always trusted. Note that you can create such an entry with only security add-certificates but not security add-trusted-cert. macOS allows anyone to run the first command but prompts you for an administrator password when running the second. The name of the second command also implies that it's the only way to assign trust to a certificate, IMHO.

Hm, after thinking about this again and also comparing with behavior of curl, I think you're right. A self-signed certificate should only be trusted if it has a trust entry (e.g. added by security add-trusted-cert). Somehow I was under the impression that self-signed certificates should be trusted when they exist. But after reading comments etc. again I'm not sure why I thought so at all. 😜 Will update the PR...

wangweij · 2023-05-19T20:27:24Z

src/java.base/macosx/classes/apple/security/KeychainStore.java

@@ -804,8 +803,26 @@ private void createTrustedCertEntry(String alias, List<String> inputTrust,
            tce.cert = cert;
            tce.certRef = keychainItemRef;

+            // Check whether a certificate with same alias already exists and is the same
+            // If yes, we can return here - the existing entry must have the same
+            // properties and trust settings


This is always true, right? I'm not sure how this could happen.

This handles the case, when a certificate is in both, the login (user) and system keychain.

How do you know "the existing entry must have the same properties and trust settings"?

Trust settings are stored per certificate. That is, when you do security add-trusted-cert, you have to pass a certificate that the entry is created for. It does not matter then, if the certificate is actually present/loaded into any keychain. If the certificate is not in the keychain, a security dump-trust-settings will not show the trust entry then but after you add it, it gets visible.

So, that means, if two certificates are the same, no matter if they were loaded from different keychains or under different aliases (don't know whether the latter is possible though), they will share the same trust records.

I see. Thanks.

wangweij · 2023-05-19T20:28:42Z

Since you removed the key usage checks, can you update the PR description please?

RealCLanger · 2023-05-21T21:30:04Z

Since you removed the key usage checks, can you update the PR description please?

Done.

wangweij · 2023-05-23T13:50:48Z

The code change looks fine to me. Thanks.

Since this is rather a big behavior change, I think a CSR and a release note are required. The previous release note on this is at https://www.oracle.com/java/technologies/javase/19-relnote-issues.html#JDK-8278449.

RealCLanger · 2023-05-23T15:55:04Z

The code change looks fine to me. Thanks.

Since this is rather a big behavior change, I think a CSR and a release note are required. The previous release note on this is at https://www.oracle.com/java/technologies/javase/19-relnote-issues.html#JDK-8278449.

Thanks for the review. As for CSR and release note, I guess one could do both, sure. However, it's quite a bit of overhead. And, for JDK-8278449, I don't see a CSR either. 😉 I would consider this change rather as a bugfix for JDK-8278449. So, if you really want me to do it, I'll do it. But please help me to get this processed quickly as I want to get this fix integrated ideally through this week. Please let me know your decision. Thanks.

wangweij · 2023-05-23T17:05:13Z

I've started the CSR at https://bugs.openjdk.org/browse/JDK-8308690. Please edit if there is any issue. At the same time, please write a release note. See https://openjdk.org/guide/#release-notes for the process.

RealCLanger · 2023-05-23T21:18:37Z

I've started the CSR at https://bugs.openjdk.org/browse/JDK-8308690. Please edit if there is any issue. At the same time, please write a release note. See https://openjdk.org/guide/#release-notes for the process.

Thanks. I've created a release note and Edited the CSR. Please review both. When you are fine with the CSR, I can finalize it.

wangweij · 2023-05-27T22:47:53Z

I think you can finalize the CSR now.

RealCLanger · 2023-05-30T08:59:30Z

I think you can finalize the CSR now.

Thx for the hint, done.

RealCLanger · 2023-06-04T06:19:46Z

@wangweij The CSR is approved. Would you like to review/approve the PR now?

RealCLanger · 2023-06-05T08:35:18Z

Thx.
/integrate

openjdk · 2023-06-05T08:36:59Z

Going to push as commit ac41c03.
Since your change was applied there have been 234 commits pushed to the master branch:

11fb5b2: 8309104: [JVMCI] compiler/unsafe/UnsafeGetStableArrayElement test asserts wrong values with Graal
a02d800: 8309405: RISC-V: is_deopt may produce unaligned memory read
3fa776d: 8302673: [SuperWord] MaxReduction and MinReduction should vectorize for int
22a9a86: 8309268: C2: "assert(in_bb(n)) failed: must be" after JDK-8306302
b6c9232: 8305225: A service broken error despite annotation processor generating it if directives listed
05fb6c6: 8309336: Incorrect switch in enum not reported properly
08c91c2: 8309332: RISC-V: Improve PrintOptoAssembly output of vector nodes
ecb1753: 8309334: ProcessTools.main() does not properly set thread names when using the virtual thread wrapper
ac1597b: 8309409: Update HttpInputStreamTest and BodyProcessorInputStreamTest to use hg.openjdk.org
fdb5893: 8309391: Remove non-failing tests from test/jdk/ProblemList-Virtual.txt
... and 224 more: https://git.openjdk.org/jdk/compare/690d3969b80776bf896fbfbfac5eabe7d074c9bb...master

Your commit was automatically rebased without conflicts.

openjdk · 2023-06-05T08:37:16Z

@RealCLanger Pushed as commit ac41c03.

💡 You may see a message that your pull request was closed with unmerged commits. This can be safely ignored.

JDK-8303465

3c4424b

openjdk bot added the rfr Pull request is ready for review label May 11, 2023

openjdk bot added the security security-dev@openjdk.org label May 11, 2023

Add some more initializations to avoid crashes

22303e1

Check return code of SecTrustSettingsCopyTrustSettings and address re…

b14e5f2

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MBaesken reviewed May 17, 2023

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RealCLanger added 4 commits May 19, 2023 13:24

Merge branch 'master' into JDK-8303465

90478ec

Do not trust self signed certificates without trust settings

890e12b

Remove further unnecessary changes

8085b90

Remove another obsolete comment

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wangweij reviewed May 19, 2023

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openjdk bot added csr Pull request needs approved CSR before integration and removed ready Pull request is ready to be integrated labels May 23, 2023

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RealCLanger deleted the JDK-8303465 branch June 5, 2023 08:42

8303465: KeyStore of type KeychainStore, provider Apple does not show all trusted certificates #13945

8303465: KeyStore of type KeychainStore, provider Apple does not show all trusted certificates #13945

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