Can't use PEM encoded PKCS#8 EC keys with server.ssl.certificate-private-key #35322

kumarvijay95 · 2023-05-05T10:45:30Z

Getting this issue with spring boot properties:

server.ssl.certificate-private-key=/privkey.pem
server.ssl.certificate=/fullchain.pem

org.springframework.context.ApplicationContextException: Unable to start web server
        at org.springframework.boot.web.servlet.context.ServletWebServerApplicationContext.onRefresh(ServletWebServerApplicationContext.java:164) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.context.support.AbstractApplicationContext.refresh(AbstractApplicationContext.java:578) ~[spring-context-6.0.8.jar!/:6.0.8]
        at org.springframework.boot.web.servlet.context.ServletWebServerApplicationContext.refresh(ServletWebServerApplicationContext.java:146) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.SpringApplication.refresh(SpringApplication.java:733) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.SpringApplication.refreshContext(SpringApplication.java:435) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.SpringApplication.run(SpringApplication.java:311) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.SpringApplication.run(SpringApplication.java:1305) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.SpringApplication.run(SpringApplication.java:1294) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at com.smarthome.resourceserver.ResourceserverApplication.main(ResourceserverApplication.java:11) ~[classes!/:0.0.1-SNAPSHOT]
        at java.base/jdk.internal.reflect.NativeMethodAccessorImpl.invoke0(Native Method) ~[na:na]
        at java.base/jdk.internal.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:77) ~[na:na]
        at java.base/jdk.internal.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) ~[na:na]
        at java.base/java.lang.reflect.Method.invoke(Method.java:568) ~[na:na]
        at org.springframework.boot.loader.MainMethodRunner.run(MainMethodRunner.java:49) ~[resourceserver-0.0.1-SNAPSHOT.jar:0.0.1-SNAPSHOT]
        at org.springframework.boot.loader.Launcher.launch(Launcher.java:95) ~[resourceserver-0.0.1-SNAPSHOT.jar:0.0.1-SNAPSHOT]
        at org.springframework.boot.loader.Launcher.launch(Launcher.java:58) ~[resourceserver-0.0.1-SNAPSHOT.jar:0.0.1-SNAPSHOT]
        at org.springframework.boot.loader.JarLauncher.main(JarLauncher.java:65) ~[resourceserver-0.0.1-SNAPSHOT.jar:0.0.1-SNAPSHOT]
Caused by: java.lang.IllegalStateException: Could not load store: Unable to create key store: Error loading private key file: Unexpected key format
        at org.springframework.boot.web.embedded.tomcat.SslConnectorCustomizer.configureSslStoreProvider(SslConnectorCustomizer.java:124) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.web.embedded.tomcat.SslConnectorCustomizer.configureSsl(SslConnectorCustomizer.java:93) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.web.embedded.tomcat.SslConnectorCustomizer.customize(SslConnectorCustomizer.java:59) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.web.embedded.tomcat.TomcatServletWebServerFactory.customizeSsl(TomcatServletWebServerFactory.java:367) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.web.embedded.tomcat.TomcatServletWebServerFactory.customizeConnector(TomcatServletWebServerFactory.java:344) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.web.embedded.tomcat.TomcatServletWebServerFactory.getWebServer(TomcatServletWebServerFactory.java:203) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.web.servlet.context.ServletWebServerApplicationContext.createWebServer(ServletWebServerApplicationContext.java:183) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.web.servlet.context.ServletWebServerApplicationContext.onRefresh(ServletWebServerApplicationContext.java:161) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        ... 16 common frames omitted
Caused by: java.lang.IllegalStateException: Unable to create key store: Error loading private key file: Unexpected key format
        at org.springframework.boot.ssl.pem.PemSslStoreBundle.createKeyStore(PemSslStoreBundle.java:99) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.ssl.pem.PemSslStoreBundle.getKeyStore(PemSslStoreBundle.java:69) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.web.embedded.tomcat.SslConnectorCustomizer.configureSslStoreProvider(SslConnectorCustomizer.java:116) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        ... 23 common frames omitted
Caused by: java.lang.IllegalStateException: Error loading private key file: Unexpected key format
        at org.springframework.boot.ssl.pem.PemPrivateKeyParser.parse(PemPrivateKeyParser.java:126) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.ssl.pem.PemSslStoreBundle.createKeyStore(PemSslStoreBundle.java:94) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        ... 25 common frames omitted
Caused by: java.lang.IllegalArgumentException: Unexpected key format
        at org.springframework.boot.ssl.pem.PemPrivateKeyParser$PemParser.parse(PemPrivateKeyParser.java:165) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.ssl.pem.PemPrivateKeyParser$PemParser.parse(PemPrivateKeyParser.java:150) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        at org.springframework.boot.ssl.pem.PemPrivateKeyParser.parse(PemPrivateKeyParser.java:118) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        ... 26 common frames omitted
Caused by: java.security.spec.InvalidKeySpecException: java.security.InvalidKeyException: Invalid RSA private key
        at java.base/sun.security.rsa.RSAKeyFactory.engineGeneratePrivate(RSAKeyFactory.java:253) ~[na:na]
        at java.base/java.security.KeyFactory.generatePrivate(KeyFactory.java:389) ~[na:na]
        at org.springframework.boot.ssl.pem.PemPrivateKeyParser$PemParser.parse(PemPrivateKeyParser.java:162) ~[spring-boot-3.1.0-SNAPSHOT.jar!/:3.1.0-SNAPSHOT]
        ... 28 common frames omitted
Caused by: java.security.InvalidKeyException: Invalid RSA private key
        at java.base/sun.security.rsa.RSAPrivateCrtKeyImpl.parseKeyBits(RSAPrivateCrtKeyImpl.java:361) ~[na:na]
        at java.base/sun.security.rsa.RSAPrivateCrtKeyImpl.<init>(RSAPrivateCrtKeyImpl.java:161) ~[na:na]
        at java.base/sun.security.rsa.RSAPrivateCrtKeyImpl.newKey(RSAPrivateCrtKeyImpl.java:90) ~[na:na]
        at java.base/sun.security.rsa.RSAKeyFactory.generatePrivate(RSAKeyFactory.java:352) ~[na:na]
        at java.base/sun.security.rsa.RSAKeyFactory.engineGeneratePrivate(RSAKeyFactory.java:249) ~[na:na]
        ... 30 common frames omitted
Caused by: java.io.IOException: Version must be 0
        at java.base/sun.security.rsa.RSAPrivateCrtKeyImpl.parseASN1(RSAPrivateCrtKeyImpl.java:326) ~[na:na]
        at java.base/sun.security.rsa.RSAPrivateCrtKeyImpl.parseKeyBits(RSAPrivateCrtKeyImpl.java:351) ~[na:na]
        ... 34 common frames omitted

The text was updated successfully, but these errors were encountered:

kumarvijay95 · 2023-05-05T10:46:18Z

Earlier It was working fine with same configurations

mhalbritter · 2023-05-05T12:01:17Z

Hello! How did you create the RSA key?

kumarvijay95 · 2023-05-05T15:08:12Z

Through Letsencrypt site. @mhalbritter

mhalbritter · 2023-05-08T06:12:51Z

Could you generate a key pair for us with which we can reproduce the issue? I couldn't find that letsencrypt site you mentioned. Do you mean certbot?

kumarvijay95 · 2023-05-08T06:38:03Z

@mhalbritter Sorry.. yes It is certbot.

kumarvijay95 · 2023-05-08T10:39:01Z

@mhalbritter is this a bug in spring ??

mhalbritter · 2023-05-08T11:56:50Z

I don't know. I didn't managed to get a RSA key generated by certbot yet. If you could provide us one, that would help greatly.

mhalbritter · 2023-05-08T12:47:13Z

I just tried it with Java 17 and Spring Boot 3.0.6 / 3.1.0-RC2 / 3.1.0-SNAPSHOT and a certbot generated RSA key and can't reproduce it.

kumarvijay95 · 2023-05-09T05:38:32Z

@mhalbritter Let me check it again.. Could you pls check it with Java 11 and Spring Boot 2.7.7

kumarvijay95 · 2023-05-09T09:02:36Z

@mhalbritter could you please send me the properties because I am getting the same issue again.

mhalbritter · 2023-05-09T09:33:46Z

It works with Java 11 and Spring Boot 2.7.7, too.

My properties don't help you, because something is wrong with your private key. Until you upload a sample with which we can reproduce the issue I fear that we can't help you here.

kumarvijay95 · 2023-05-09T10:29:36Z

@mhalbritter I have pasted the privkey.pem and fullchain.pem file as it was not allowing to upload .pem extension files.

mhalbritter · 2023-05-09T11:11:29Z

Thanks, I can now reproduce the issue. This key is not a RSA key, its a 256 bit elliptic curve key. That seems like a bug in boot.

mhalbritter · 2023-05-09T11:14:56Z

keys.zip

This ZIP file contains a EC 256 bit key and the certificate for it. This leads to the stacktrace from the first comment. It looks like Boot tries to load it as a RSA key, which fails.

Looks like that Spring Boot 2.7.x is affected, too:

org.springframework.context.ApplicationContextException: Unable to start web server; nested exception is org.springframework.boot.web.server.WebServerException: Could not load store: Error loading private key file /home/moe/Desktop/key.pem
        at org.springframework.boot.web.servlet.context.ServletWebServerApplicationContext.onRefresh(ServletWebServerApplicationContext.java:165) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.context.support.AbstractApplicationContext.refresh(AbstractApplicationContext.java:577) ~[spring-context-5.3.27.jar:5.3.27]
        at org.springframework.boot.web.servlet.context.ServletWebServerApplicationContext.refresh(ServletWebServerApplicationContext.java:147) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.SpringApplication.refresh(SpringApplication.java:731) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.SpringApplication.refreshContext(SpringApplication.java:408) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.SpringApplication.run(SpringApplication.java:307) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.SpringApplication.run(SpringApplication.java:1303) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.SpringApplication.run(SpringApplication.java:1292) ~[spring-boot-2.7.11.jar:2.7.11]
        at com.example.sb35322.Sb35322Application.main(Sb35322Application.java:10) ~[main/:na]
Caused by: org.springframework.boot.web.server.WebServerException: Could not load store: Error loading private key file /home/moe/Desktop/key.pem
        at org.springframework.boot.web.embedded.tomcat.SslConnectorCustomizer.configureSslStoreProvider(SslConnectorCustomizer.java:138) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.web.embedded.tomcat.SslConnectorCustomizer.configureSsl(SslConnectorCustomizer.java:96) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.web.embedded.tomcat.SslConnectorCustomizer.customize(SslConnectorCustomizer.java:61) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.web.embedded.tomcat.TomcatServletWebServerFactory.customizeSsl(TomcatServletWebServerFactory.java:366) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.web.embedded.tomcat.TomcatServletWebServerFactory.customizeConnector(TomcatServletWebServerFactory.java:343) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.web.embedded.tomcat.TomcatServletWebServerFactory.getWebServer(TomcatServletWebServerFactory.java:203) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.web.servlet.context.ServletWebServerApplicationContext.createWebServer(ServletWebServerApplicationContext.java:184) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.web.servlet.context.ServletWebServerApplicationContext.onRefresh(ServletWebServerApplicationContext.java:162) ~[spring-boot-2.7.11.jar:2.7.11]
        ... 8 common frames omitted
Caused by: java.lang.IllegalStateException: Error loading private key file /home/moe/Desktop/key.pem
        at org.springframework.boot.web.server.PrivateKeyParser.parse(PrivateKeyParser.java:130) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.web.server.CertificateFileSslStoreProvider.createKeyStore(CertificateFileSslStoreProvider.java:83) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.web.server.CertificateFileSslStoreProvider.getKeyStore(CertificateFileSslStoreProvider.java:51) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.web.embedded.tomcat.SslConnectorCustomizer.configureSslStoreProvider(SslConnectorCustomizer.java:130) ~[spring-boot-2.7.11.jar:2.7.11]
        ... 15 common frames omitted
Caused by: java.lang.IllegalArgumentException: Unexpected key format
        at org.springframework.boot.web.server.PrivateKeyParser$PemParser.parse(PrivateKeyParser.java:176) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.web.server.PrivateKeyParser$PemParser.parse(PrivateKeyParser.java:161) ~[spring-boot-2.7.11.jar:2.7.11]
        at org.springframework.boot.web.server.PrivateKeyParser.parse(PrivateKeyParser.java:122) ~[spring-boot-2.7.11.jar:2.7.11]
        ... 18 common frames omitted
Caused by: java.security.spec.InvalidKeySpecException: java.security.InvalidKeyException: Invalid RSA private key
        at java.base/sun.security.rsa.RSAKeyFactory.engineGeneratePrivate(RSAKeyFactory.java:253) ~[na:na]
        at java.base/java.security.KeyFactory.generatePrivate(KeyFactory.java:389) ~[na:na]
        at org.springframework.boot.web.server.PrivateKeyParser$PemParser.parse(PrivateKeyParser.java:173) ~[spring-boot-2.7.11.jar:2.7.11]
        ... 20 common frames omitted
Caused by: java.security.InvalidKeyException: Invalid RSA private key
        at java.base/sun.security.rsa.RSAPrivateCrtKeyImpl.parseKeyBits(RSAPrivateCrtKeyImpl.java:361) ~[na:na]
        at java.base/sun.security.rsa.RSAPrivateCrtKeyImpl.<init>(RSAPrivateCrtKeyImpl.java:161) ~[na:na]
        at java.base/sun.security.rsa.RSAPrivateCrtKeyImpl.newKey(RSAPrivateCrtKeyImpl.java:90) ~[na:na]
        at java.base/sun.security.rsa.RSAKeyFactory.generatePrivate(RSAKeyFactory.java:352) ~[na:na]
        at java.base/sun.security.rsa.RSAKeyFactory.engineGeneratePrivate(RSAKeyFactory.java:249) ~[na:na]
        ... 22 common frames omitted
Caused by: java.io.IOException: Version must be 0
        at java.base/sun.security.rsa.RSAPrivateCrtKeyImpl.parseASN1(RSAPrivateCrtKeyImpl.java:326) ~[na:na]
        at java.base/sun.security.rsa.RSAPrivateCrtKeyImpl.parseKeyBits(RSAPrivateCrtKeyImpl.java:351) ~[na:na]
        ... 26 common frames omitted

mhalbritter · 2023-05-09T11:25:00Z

Problem is that in org.springframework.boot.web.server.PrivateKeyParser, this parser is used for parsing the key:

parsers.add(new PemParser(PKCS8_HEADER, PKCS8_FOOTER, "RSA", PKCS8EncodedKeySpec::new));

Which sets the algorithm to RSA. This is not correct in this case, it has to be "EC". Seems we need a more sophisticated logic to parse PKCS#8 keys which are not RSA keys.

TomerBu · 2023-05-09T13:20:30Z

Facing the same issue:
is there a workaround for the time being? some property we can set in application.properties?
Export the key to another algorithm using openssh?
Or a configuration bean to configure it correctly?

kumarvijay95 · 2023-05-09T13:48:05Z

@mhalbritter when will it be released ??

wilkinsona · 2023-05-09T14:11:37Z

@kumarvijay95 you can find that information yourself by looking at the milestone to which the issue has been assigned (2.7.12 and 3.0.7 for the forward port) and their due dates (18 May).

mhalbritter · 2023-05-09T15:34:28Z

Hey @TomerBu: RSA keys work fine, but I doubt you'll find a way to convert the EC key to RSA. Did you get the EC key through certbot, too? Maybe there's an option in certbot to force RSA keys?

You can also add the keys into a Java KeyStore, which you can then configure through the properties. That should work with EC keys, as the bug is in our own PEM parser. See this documentation for details.

Polish and port support for PKCS#8 PEM encoded EC and DSA keys to the buildpack code. See gh-35322

TomerBu · 2023-05-14T12:15:51Z

Hey @TomerBu: RSA keys work fine, but I doubt you'll find a way to convert the EC key to RSA. Did you get the EC key through certbot, too? Maybe there's an option in certbot to force RSA keys?

You can also add the keys into a Java KeyStore, which you can then configure through the properties. That should work with EC keys, as the bug is in our own PEM parser. See this documentation for details.

Yes. that's what I did and it works.
for anyone with the same issue:
certbot certonly --standalone --key-type rsa

we can also renew an existing certificate:
certbot renew --key-type rsa --cert-name mydomain.com --force-renewal

Thank you!

mhalbritter · 2023-05-15T06:21:31Z

Thanks for providing that workaround!

spring-projects-issues added the status: waiting-for-triage An issue we've not yet triaged label May 5, 2023

mhalbritter added the status: waiting-for-feedback We need additional information before we can continue label May 5, 2023

spring-projects-issues added status: feedback-provided Feedback has been provided and removed status: waiting-for-feedback We need additional information before we can continue labels May 5, 2023

mhalbritter added status: waiting-for-feedback We need additional information before we can continue and removed status: feedback-provided Feedback has been provided labels May 8, 2023

spring-projects-issues added status: feedback-provided Feedback has been provided and removed status: waiting-for-feedback We need additional information before we can continue labels May 8, 2023

mhalbritter changed the title ~~Invalid RSA Key while applying SSL with pem files~~ Invalid RSA Key when using CertBot generated PEM file May 8, 2023

mhalbritter changed the title ~~Invalid RSA Key when using CertBot generated PEM file~~ Invalid RSA private key when using CertBot generated PEM file May 8, 2023

mhalbritter added status: waiting-for-feedback We need additional information before we can continue and removed status: feedback-provided Feedback has been provided labels May 8, 2023

spring-projects-issues added status: feedback-provided Feedback has been provided and removed status: waiting-for-feedback We need additional information before we can continue labels May 9, 2023

mhalbritter closed this as not planned Won't fix, can't repro, duplicate, stale May 9, 2023

mhalbritter added status: invalid An issue that we don't feel is valid and removed status: waiting-for-triage An issue we've not yet triaged status: feedback-provided Feedback has been provided labels May 9, 2023

mhalbritter reopened this May 9, 2023

mhalbritter added status: waiting-for-triage An issue we've not yet triaged and removed status: invalid An issue that we don't feel is valid labels May 9, 2023

spring-projects deleted a comment from kumarvijay95 May 9, 2023

mhalbritter changed the title ~~Invalid RSA private key when using CertBot generated PEM file~~ Can't use PEM encoded EC keys with server.ssl.certificate-private-key May 9, 2023

mhalbritter added type: bug A general bug and removed status: waiting-for-triage An issue we've not yet triaged labels May 9, 2023

mhalbritter added this to the 2.7.x milestone May 9, 2023

mhalbritter changed the title ~~Can't use PEM encoded EC keys with server.ssl.certificate-private-key~~ Can't use PEM encoded PKCS#8 EC keys with server.ssl.certificate-private-key May 9, 2023

mhalbritter self-assigned this May 9, 2023

This was referenced May 9, 2023

Can't use PEM encoded PKCS#8 EC keys with server.ssl.certificate-private-key #35364

Closed

Can't use PEM encoded PKCS#8 EC keys with server.ssl.certificate-private-key #35365

Closed

mhalbritter modified the milestones: 2.7.x, 2.7.12 May 9, 2023

mhalbritter closed this as completed in c238049 May 9, 2023

philwebb added the theme: ssl Issues related to ssl support label May 11, 2023

philwebb added a commit that referenced this issue May 12, 2023

Fix loading of PKCS#8 PEM encoded EC and DSA keys for buildpack

ef4b097

Polish and port support for PKCS#8 PEM encoded EC and DSA keys to the buildpack code. See gh-35322

Netyyyy mentioned this issue May 25, 2023

External dependencies upgrade - Spring Boot 2.7.12 and Spring Cloud 2021.0.7 Azure/azure-sdk-for-java#35148

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Netyyyy mentioned this issue Jun 19, 2023

External dependencies upgrade - Spring Boot 2.7.12 and Spring Cloud 2021.0.7 Azure/azure-sdk-for-java#35514

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Can't use PEM encoded PKCS#8 EC keys with server.ssl.certificate-private-key #35322

Can't use PEM encoded PKCS#8 EC keys with server.ssl.certificate-private-key #35322

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Can't use PEM encoded PKCS#8 EC keys with server.ssl.certificate-private-key #35322

Can't use PEM encoded PKCS#8 EC keys with server.ssl.certificate-private-key #35322

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