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2-way SSL with apache forward proxy



Announcing the arrival of Valued Associate #679: Cesar Manara
Planned maintenance scheduled April 17/18, 2019 at 00:00UTC (8:00pm US/Eastern)
Come Celebrate our 10 Year Anniversary!Trouble with mod_proxy and mongrel_railsSSL certificate proxy redirect to port mongrel rails app helpWhen Using Reverse Proxy, Backend Server Does 301 Back to The Proxy Server or Changes URLSetting up SSL certificates with ApacheHow to Proxypass on Apache?Apache SSL reverse proxy breaks Liferay AuthenticationApache Proxy - SSL Authentication failure on back end of proxy (Client side)What is wrong with this attempt to serve up static content? Does a Proxy/ReverseProxy trump Alias, or can I ask for Alias to trump proxy?Apache reverse proxy location based access control not workingSetting up an Apache forward proxy with 2-way SSL with certificate CN check fails



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2















I'm working to set up Apache as a forward proxy with a client that uses 2-way SSL. The basic flow is myApplication --via http--> Apache proxy --via 2 way SSL--> client. After setting everything up, when I try to start Apache, I'm getting a "incomplete client cert configured for SSL proxy (missing or encrypted private key?)" error. What I can't figure out is that the client cert I'm using in the SSLProxyMachineCertificateFile directive has both the unencrypted private key and the public cert already. Any suggestions on what I'm missing and/or anything else I can try? Does the all-in-one machine cert need to have the chain in it as well?



Here's what my vhost looks like.



<VirtualHost *:8082>
ServerName my.domain.com

ProxyRequests On
SSLProxyEngine On

SSLProxyMachineCertificateFile /etc/httpd/keys/machine.pem
SSLProxyCACertificateFile /etc/httpd/keys/machine.chain.crt

ProxyPass / https://target.client.com/
ProxyPassReverse / https://target.client.com/

<Proxy *>
Order deny,allow
Allow from all
</Proxy>
</VirtualHost>


EDIT: I updated the basic flow to clarify what kind of connection I'm trying to use between the application, apache, and the client.










share|improve this question
























  • what is 2-way-SSL?

    – that guy from over there
    Oct 15 '13 at 5:21











  • Is the private key in machine.pem DES encrypted (the default when generating)?

    – Shane Madden
    Oct 15 '13 at 6:11











  • The all-in-one machine cert should not need to have the chain in it. I would start by trying to connect using without apache, e.g. by doing openssl s_client -connect remoteserver:443 -cert /etc/httpd/keys/machine.pem. The output from that should give you some hint.

    – Jenny D
    Oct 15 '13 at 7:48











  • @ShaneMadden I'm going to say yes. When I generated the key and csr it was a pretty standard generation process and I didn't put a password on the private key.

    – Mike Levy
    Oct 15 '13 at 14:50











  • @JennyD I tried out your suggestion and was able to successfully connect to the remote server using machine.pem. However, I still can't start Apache when using machine.pem as the SSLProxyMachineCertificateFile.

    – Mike Levy
    Oct 15 '13 at 15:04

















2















I'm working to set up Apache as a forward proxy with a client that uses 2-way SSL. The basic flow is myApplication --via http--> Apache proxy --via 2 way SSL--> client. After setting everything up, when I try to start Apache, I'm getting a "incomplete client cert configured for SSL proxy (missing or encrypted private key?)" error. What I can't figure out is that the client cert I'm using in the SSLProxyMachineCertificateFile directive has both the unencrypted private key and the public cert already. Any suggestions on what I'm missing and/or anything else I can try? Does the all-in-one machine cert need to have the chain in it as well?



Here's what my vhost looks like.



<VirtualHost *:8082>
ServerName my.domain.com

ProxyRequests On
SSLProxyEngine On

SSLProxyMachineCertificateFile /etc/httpd/keys/machine.pem
SSLProxyCACertificateFile /etc/httpd/keys/machine.chain.crt

ProxyPass / https://target.client.com/
ProxyPassReverse / https://target.client.com/

<Proxy *>
Order deny,allow
Allow from all
</Proxy>
</VirtualHost>


EDIT: I updated the basic flow to clarify what kind of connection I'm trying to use between the application, apache, and the client.










share|improve this question
























  • what is 2-way-SSL?

    – that guy from over there
    Oct 15 '13 at 5:21











  • Is the private key in machine.pem DES encrypted (the default when generating)?

    – Shane Madden
    Oct 15 '13 at 6:11











  • The all-in-one machine cert should not need to have the chain in it. I would start by trying to connect using without apache, e.g. by doing openssl s_client -connect remoteserver:443 -cert /etc/httpd/keys/machine.pem. The output from that should give you some hint.

    – Jenny D
    Oct 15 '13 at 7:48











  • @ShaneMadden I'm going to say yes. When I generated the key and csr it was a pretty standard generation process and I didn't put a password on the private key.

    – Mike Levy
    Oct 15 '13 at 14:50











  • @JennyD I tried out your suggestion and was able to successfully connect to the remote server using machine.pem. However, I still can't start Apache when using machine.pem as the SSLProxyMachineCertificateFile.

    – Mike Levy
    Oct 15 '13 at 15:04













2












2








2


1






I'm working to set up Apache as a forward proxy with a client that uses 2-way SSL. The basic flow is myApplication --via http--> Apache proxy --via 2 way SSL--> client. After setting everything up, when I try to start Apache, I'm getting a "incomplete client cert configured for SSL proxy (missing or encrypted private key?)" error. What I can't figure out is that the client cert I'm using in the SSLProxyMachineCertificateFile directive has both the unencrypted private key and the public cert already. Any suggestions on what I'm missing and/or anything else I can try? Does the all-in-one machine cert need to have the chain in it as well?



Here's what my vhost looks like.



<VirtualHost *:8082>
ServerName my.domain.com

ProxyRequests On
SSLProxyEngine On

SSLProxyMachineCertificateFile /etc/httpd/keys/machine.pem
SSLProxyCACertificateFile /etc/httpd/keys/machine.chain.crt

ProxyPass / https://target.client.com/
ProxyPassReverse / https://target.client.com/

<Proxy *>
Order deny,allow
Allow from all
</Proxy>
</VirtualHost>


EDIT: I updated the basic flow to clarify what kind of connection I'm trying to use between the application, apache, and the client.










share|improve this question
















I'm working to set up Apache as a forward proxy with a client that uses 2-way SSL. The basic flow is myApplication --via http--> Apache proxy --via 2 way SSL--> client. After setting everything up, when I try to start Apache, I'm getting a "incomplete client cert configured for SSL proxy (missing or encrypted private key?)" error. What I can't figure out is that the client cert I'm using in the SSLProxyMachineCertificateFile directive has both the unencrypted private key and the public cert already. Any suggestions on what I'm missing and/or anything else I can try? Does the all-in-one machine cert need to have the chain in it as well?



Here's what my vhost looks like.



<VirtualHost *:8082>
ServerName my.domain.com

ProxyRequests On
SSLProxyEngine On

SSLProxyMachineCertificateFile /etc/httpd/keys/machine.pem
SSLProxyCACertificateFile /etc/httpd/keys/machine.chain.crt

ProxyPass / https://target.client.com/
ProxyPassReverse / https://target.client.com/

<Proxy *>
Order deny,allow
Allow from all
</Proxy>
</VirtualHost>


EDIT: I updated the basic flow to clarify what kind of connection I'm trying to use between the application, apache, and the client.







apache-2.2 ssl proxy forwarding virtualhost






share|improve this question















share|improve this question













share|improve this question




share|improve this question








edited Oct 15 '13 at 15:24







Mike Levy

















asked Oct 15 '13 at 4:58









Mike LevyMike Levy

150126




150126












  • what is 2-way-SSL?

    – that guy from over there
    Oct 15 '13 at 5:21











  • Is the private key in machine.pem DES encrypted (the default when generating)?

    – Shane Madden
    Oct 15 '13 at 6:11











  • The all-in-one machine cert should not need to have the chain in it. I would start by trying to connect using without apache, e.g. by doing openssl s_client -connect remoteserver:443 -cert /etc/httpd/keys/machine.pem. The output from that should give you some hint.

    – Jenny D
    Oct 15 '13 at 7:48











  • @ShaneMadden I'm going to say yes. When I generated the key and csr it was a pretty standard generation process and I didn't put a password on the private key.

    – Mike Levy
    Oct 15 '13 at 14:50











  • @JennyD I tried out your suggestion and was able to successfully connect to the remote server using machine.pem. However, I still can't start Apache when using machine.pem as the SSLProxyMachineCertificateFile.

    – Mike Levy
    Oct 15 '13 at 15:04

















  • what is 2-way-SSL?

    – that guy from over there
    Oct 15 '13 at 5:21











  • Is the private key in machine.pem DES encrypted (the default when generating)?

    – Shane Madden
    Oct 15 '13 at 6:11











  • The all-in-one machine cert should not need to have the chain in it. I would start by trying to connect using without apache, e.g. by doing openssl s_client -connect remoteserver:443 -cert /etc/httpd/keys/machine.pem. The output from that should give you some hint.

    – Jenny D
    Oct 15 '13 at 7:48











  • @ShaneMadden I'm going to say yes. When I generated the key and csr it was a pretty standard generation process and I didn't put a password on the private key.

    – Mike Levy
    Oct 15 '13 at 14:50











  • @JennyD I tried out your suggestion and was able to successfully connect to the remote server using machine.pem. However, I still can't start Apache when using machine.pem as the SSLProxyMachineCertificateFile.

    – Mike Levy
    Oct 15 '13 at 15:04
















what is 2-way-SSL?

– that guy from over there
Oct 15 '13 at 5:21





what is 2-way-SSL?

– that guy from over there
Oct 15 '13 at 5:21













Is the private key in machine.pem DES encrypted (the default when generating)?

– Shane Madden
Oct 15 '13 at 6:11





Is the private key in machine.pem DES encrypted (the default when generating)?

– Shane Madden
Oct 15 '13 at 6:11













The all-in-one machine cert should not need to have the chain in it. I would start by trying to connect using without apache, e.g. by doing openssl s_client -connect remoteserver:443 -cert /etc/httpd/keys/machine.pem. The output from that should give you some hint.

– Jenny D
Oct 15 '13 at 7:48





The all-in-one machine cert should not need to have the chain in it. I would start by trying to connect using without apache, e.g. by doing openssl s_client -connect remoteserver:443 -cert /etc/httpd/keys/machine.pem. The output from that should give you some hint.

– Jenny D
Oct 15 '13 at 7:48













@ShaneMadden I'm going to say yes. When I generated the key and csr it was a pretty standard generation process and I didn't put a password on the private key.

– Mike Levy
Oct 15 '13 at 14:50





@ShaneMadden I'm going to say yes. When I generated the key and csr it was a pretty standard generation process and I didn't put a password on the private key.

– Mike Levy
Oct 15 '13 at 14:50













@JennyD I tried out your suggestion and was able to successfully connect to the remote server using machine.pem. However, I still can't start Apache when using machine.pem as the SSLProxyMachineCertificateFile.

– Mike Levy
Oct 15 '13 at 15:04





@JennyD I tried out your suggestion and was able to successfully connect to the remote server using machine.pem. However, I still can't start Apache when using machine.pem as the SSLProxyMachineCertificateFile.

– Mike Levy
Oct 15 '13 at 15:04










1 Answer
1






active

oldest

votes


















0














Your PEM file is not the correct format. Checkout this post.



http://projectzme.wordpress.com/2013/02/02/tip-sslproxymachinecertificatefile-returns-missing-or-encrypted-private-key/






share|improve this answer























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    1 Answer
    1






    active

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    active

    oldest

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    active

    oldest

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    0














    Your PEM file is not the correct format. Checkout this post.



    http://projectzme.wordpress.com/2013/02/02/tip-sslproxymachinecertificatefile-returns-missing-or-encrypted-private-key/






    share|improve this answer



























      0














      Your PEM file is not the correct format. Checkout this post.



      http://projectzme.wordpress.com/2013/02/02/tip-sslproxymachinecertificatefile-returns-missing-or-encrypted-private-key/






      share|improve this answer

























        0












        0








        0







        Your PEM file is not the correct format. Checkout this post.



        http://projectzme.wordpress.com/2013/02/02/tip-sslproxymachinecertificatefile-returns-missing-or-encrypted-private-key/






        share|improve this answer













        Your PEM file is not the correct format. Checkout this post.



        http://projectzme.wordpress.com/2013/02/02/tip-sslproxymachinecertificatefile-returns-missing-or-encrypted-private-key/







        share|improve this answer












        share|improve this answer



        share|improve this answer










        answered Dec 13 '14 at 0:04









        annonymousannonymous

        11




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