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A workplace installs custom certificates on personal devices, can this be used to decrypt HTTPS traffic?

Corporate computers have own corporation's cert as trusted CA; should I consider all traffic compromised?Is it possible for corporation to intercept and decrypt SSL/TLS traffic?ECDHE_RSA and gmailWhy not use client certificates for premaster key generationIt is possible to decrypt HTTPS traffic when a man in the middle proxy is already in place?Details of TLS certificate verificationUnderstanding SSL man-in-the-middle and its limitationsCan a wifi router decrypt SSL/TLS information?Doubts about tls handshakeDecrypt TLS trafficStorage of certificates and keys in hardware security modules (Use-case TLS)Publishing a private key used for HTTPS certificates, is it ever OK?

2

So another engineer buddy of mine and I were having a drink the other night. He mentioned that you're allowed to use personal devices on the office wifi, but that they install a custom certificate so they can MITM your traffic.

Neither of us are security experts, but I know a little bit about the HTTP/TLS handshake protocol to question whether this is the case.

As far as I understand it (please forgive me if I butcher it):

• Client-Server initiate handshake, and exchange certificate from signing authority + public key + random string.




• Public key is used to decrypt a random string of characters, which is fed into a hashing algorithm and reveals a private key.




• Private key is used to decrypt the traffic that follows

We were reading this article, about how companies sometimes install certificates to decrypt outgoing traffic.

If the blog-post case is true, then how does this work? Would they get the private key using their trusted-root all uses certificate? Assuming that works, that covers the windows use-case, but what about other platforms like OSX/iOS, linux, BSD etc.?

Are there other approaches that I'm not considering, where a certificate install could be used to MitM?

tls certificates

share|improve this question

asked 2 hours ago

Scuba SteveScuba Steve

1385

• 
  
  
  

  
  

  
  
  
  
  
  

  
  
  What certificates did he install? Was it a root CA certificate? It could have just been a certificate to authenticate the radius server which is used to authorize access to the wifi. Different certificates do different tasks.
  
  – Daisetsu
  2 hours ago
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  
  I don't think he installed anything. I think his workplace was being pretty transparent about what the cert is for - we're just trying to understand if it's possible or if they're making an empty threat.
  
  – Scuba Steve
  2 hours ago
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  
  We both honestly don't care about the implications, we're really just trying to understand the scenario, because we're nerds.
  
  – Scuba Steve
  2 hours ago
  

  
  
  
  


• 
  
  
  

  
  1
  

  
  
  
  
  
  

  
  
  Oh, I see. Yes that is possible and it's not rare. They're called TLS interception proxies.
  
  – Daisetsu
  2 hours ago
  

  
  
  
  


• 
  
  
  

  
  1
  

  
  
  
  
  
  

  
  
  tlseminar.github.io/tls-interception look at the section titled "How SSL/TLS interception works"
  
  – Daisetsu
  2 hours ago
  

  
  
  
  

 | 
show 3 more comments

2

So another engineer buddy of mine and I were having a drink the other night. He mentioned that you're allowed to use personal devices on the office wifi, but that they install a custom certificate so they can MITM your traffic.

Neither of us are security experts, but I know a little bit about the HTTP/TLS handshake protocol to question whether this is the case.

As far as I understand it (please forgive me if I butcher it):

• Client-Server initiate handshake, and exchange certificate from signing authority + public key + random string.




• Public key is used to decrypt a random string of characters, which is fed into a hashing algorithm and reveals a private key.




• Private key is used to decrypt the traffic that follows

We were reading this article, about how companies sometimes install certificates to decrypt outgoing traffic.

If the blog-post case is true, then how does this work? Would they get the private key using their trusted-root all uses certificate? Assuming that works, that covers the windows use-case, but what about other platforms like OSX/iOS, linux, BSD etc.?

Are there other approaches that I'm not considering, where a certificate install could be used to MitM?

tls certificates

share|improve this question

asked 2 hours ago

Scuba SteveScuba Steve

1385

• 
  
  
  

  
  

  
  
  
  
  
  

  
  
  What certificates did he install? Was it a root CA certificate? It could have just been a certificate to authenticate the radius server which is used to authorize access to the wifi. Different certificates do different tasks.
  
  – Daisetsu
  2 hours ago
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  
  I don't think he installed anything. I think his workplace was being pretty transparent about what the cert is for - we're just trying to understand if it's possible or if they're making an empty threat.
  
  – Scuba Steve
  2 hours ago
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  
  We both honestly don't care about the implications, we're really just trying to understand the scenario, because we're nerds.
  
  – Scuba Steve
  2 hours ago
  

  
  
  
  


• 
  
  
  

  
  1
  

  
  
  
  
  
  

  
  
  Oh, I see. Yes that is possible and it's not rare. They're called TLS interception proxies.
  
  – Daisetsu
  2 hours ago
  

  
  
  
  


• 
  
  
  

  
  1
  

  
  
  
  
  
  

  
  
  tlseminar.github.io/tls-interception look at the section titled "How SSL/TLS interception works"
  
  – Daisetsu
  2 hours ago
  

  
  
  
  

 | 
show 3 more comments

So another engineer buddy of mine and I were having a drink the other night. He mentioned that you're allowed to use personal devices on the office wifi, but that they install a custom certificate so they can MITM your traffic.

Neither of us are security experts, but I know a little bit about the HTTP/TLS handshake protocol to question whether this is the case.

As far as I understand it (please forgive me if I butcher it):

• Client-Server initiate handshake, and exchange certificate from signing authority + public key + random string.




• Public key is used to decrypt a random string of characters, which is fed into a hashing algorithm and reveals a private key.




• Private key is used to decrypt the traffic that follows

We were reading this article, about how companies sometimes install certificates to decrypt outgoing traffic.

If the blog-post case is true, then how does this work? Would they get the private key using their trusted-root all uses certificate? Assuming that works, that covers the windows use-case, but what about other platforms like OSX/iOS, linux, BSD etc.?

Are there other approaches that I'm not considering, where a certificate install could be used to MitM?

tls certificates

share|improve this question

asked 2 hours ago

Scuba SteveScuba Steve

1385

share|improve this question

asked 2 hours ago

Scuba SteveScuba Steve

1385

share|improve this question

asked 2 hours ago

Scuba SteveScuba Steve

1385

asked 2 hours ago

Scuba SteveScuba Steve

1385

asked 2 hours ago

Scuba SteveScuba Steve

1385

1 Answer
1

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oldest

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5

Yes, they can MitM the traffic this way, using an internal certificate authority. There are two primary ways in which the MitM can work.

The first is to simply turn the edge gateway into a proxy, whereby TLS connections are made from the gateway to the server, and the gateway then generates server certificates on the fly from an internal CA in order to impersonate the remote server. Your system trusts the CA, so it trusts the server certificate.

The second is a slightly different take on the first. The gateway proxies the traffic similarly to the first method, except it only advertises static RSA cipher suites to the remote server. The reason for doing this is performance. With a static RSA key exchange (i.e. not Diffie-Hellman) the gateway can split the handshake as before in order to provide the client with a certificate generated via the internal CA, but instead of decrypting the content on the gateway and then re-encrypting it before proxying, it simply passes the same session key between the client and server. This way the gateway only has to decrypt the traffic once, using the captured session key, and never needs to re-encrypt it in order to proxy the traffic between client and server. This trick no longer works in TLS 1.3 as static RSA key exchange was removed.

Generally speaking this kind of TLS inspection is fairly commonplace in large organisations, particularly financials. Deploying it on BYOD devices is somewhat common, although you should consider the privacy and security implications that might arise from installing your company's internal CA certificate on your device. You need to ask yourself whether you trust that your IT security team is likely to be able to protect the signing keys, because if not then your device is liable to be MitM'ed by an attacker.

share|improve this answer

answered 2 hours ago

PolynomialPolynomial

101k31248341

• 
  
  
  

  
  

  
  
  
  
  
  

  
  
  " You need to ask yourself whether you trust that your IT security team is likely to be able to protect the signing keys." Yes exactly, I had the same thought myself.
  
  – Scuba Steve
  2 hours ago
  

  
  
  
  


• 
  
  
  

  
  2
  

  
  
  
  
  
  

  
  
  As an aside, I once assessed a TLS inspection gateway product which re-signed all HTTPS connections using the internal CA, even if the remote certificate was invalid. This allowed for a particularly effective phishing campaign in which we impersonated the company intranet and had our phishing domain automagically signed by the company CA. I suggest that you check for this vulnerability yourself by trying to visit a site which you know has an invalid (e.g. expired, or incorrect domain) certificate and seeing if the connection succeeds.
  
  – Polynomial
  2 hours ago
  
  
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  
  Amazing! I feel like pen-testing is a missed calling.
  
  – Scuba Steve
  2 hours ago
  

  
  
  
  


• 
  
  
  

  
  1
  

  
  
  
  
  
  

  
  
  FWIW even if 1.3 would allow static-RSA, it changes the key derivation to include the whole handshake (not just premaster+nonces) and MITM couldn't make those equal. This is similar to rfc7627 which fixes 'triple handshake' for 1.2, except that is optional and so MITM can force it off.
  
  – dave_thompson_085
  1 hour ago
  
  
  

  
  
  
  

add a comment | 

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5

Yes, they can MitM the traffic this way, using an internal certificate authority. There are two primary ways in which the MitM can work.

The first is to simply turn the edge gateway into a proxy, whereby TLS connections are made from the gateway to the server, and the gateway then generates server certificates on the fly from an internal CA in order to impersonate the remote server. Your system trusts the CA, so it trusts the server certificate.

The second is a slightly different take on the first. The gateway proxies the traffic similarly to the first method, except it only advertises static RSA cipher suites to the remote server. The reason for doing this is performance. With a static RSA key exchange (i.e. not Diffie-Hellman) the gateway can split the handshake as before in order to provide the client with a certificate generated via the internal CA, but instead of decrypting the content on the gateway and then re-encrypting it before proxying, it simply passes the same session key between the client and server. This way the gateway only has to decrypt the traffic once, using the captured session key, and never needs to re-encrypt it in order to proxy the traffic between client and server. This trick no longer works in TLS 1.3 as static RSA key exchange was removed.

Generally speaking this kind of TLS inspection is fairly commonplace in large organisations, particularly financials. Deploying it on BYOD devices is somewhat common, although you should consider the privacy and security implications that might arise from installing your company's internal CA certificate on your device. You need to ask yourself whether you trust that your IT security team is likely to be able to protect the signing keys, because if not then your device is liable to be MitM'ed by an attacker.

share|improve this answer

answered 2 hours ago

PolynomialPolynomial

101k31248341

• 
  
  
  

  
  

  
  
  
  
  
  

  
  
  " You need to ask yourself whether you trust that your IT security team is likely to be able to protect the signing keys." Yes exactly, I had the same thought myself.
  
  – Scuba Steve
  2 hours ago
  

  
  
  
  


• 
  
  
  

  
  2
  

  
  
  
  
  
  

  
  
  As an aside, I once assessed a TLS inspection gateway product which re-signed all HTTPS connections using the internal CA, even if the remote certificate was invalid. This allowed for a particularly effective phishing campaign in which we impersonated the company intranet and had our phishing domain automagically signed by the company CA. I suggest that you check for this vulnerability yourself by trying to visit a site which you know has an invalid (e.g. expired, or incorrect domain) certificate and seeing if the connection succeeds.
  
  – Polynomial
  2 hours ago
  
  
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  
  Amazing! I feel like pen-testing is a missed calling.
  
  – Scuba Steve
  2 hours ago
  

  
  
  
  


• 
  
  
  

  
  1
  

  
  
  
  
  
  

  
  
  FWIW even if 1.3 would allow static-RSA, it changes the key derivation to include the whole handshake (not just premaster+nonces) and MITM couldn't make those equal. This is similar to rfc7627 which fixes 'triple handshake' for 1.2, except that is optional and so MITM can force it off.
  
  – dave_thompson_085
  1 hour ago
  
  
  

  
  
  
  

add a comment | 

5

Yes, they can MitM the traffic this way, using an internal certificate authority. There are two primary ways in which the MitM can work.

The first is to simply turn the edge gateway into a proxy, whereby TLS connections are made from the gateway to the server, and the gateway then generates server certificates on the fly from an internal CA in order to impersonate the remote server. Your system trusts the CA, so it trusts the server certificate.

The second is a slightly different take on the first. The gateway proxies the traffic similarly to the first method, except it only advertises static RSA cipher suites to the remote server. The reason for doing this is performance. With a static RSA key exchange (i.e. not Diffie-Hellman) the gateway can split the handshake as before in order to provide the client with a certificate generated via the internal CA, but instead of decrypting the content on the gateway and then re-encrypting it before proxying, it simply passes the same session key between the client and server. This way the gateway only has to decrypt the traffic once, using the captured session key, and never needs to re-encrypt it in order to proxy the traffic between client and server. This trick no longer works in TLS 1.3 as static RSA key exchange was removed.

Generally speaking this kind of TLS inspection is fairly commonplace in large organisations, particularly financials. Deploying it on BYOD devices is somewhat common, although you should consider the privacy and security implications that might arise from installing your company's internal CA certificate on your device. You need to ask yourself whether you trust that your IT security team is likely to be able to protect the signing keys, because if not then your device is liable to be MitM'ed by an attacker.

share|improve this answer

answered 2 hours ago

PolynomialPolynomial

101k31248341

• 
  
  
  

  
  

  
  
  
  
  
  

  
  
  " You need to ask yourself whether you trust that your IT security team is likely to be able to protect the signing keys." Yes exactly, I had the same thought myself.
  
  – Scuba Steve
  2 hours ago
  

  
  
  
  


• 
  
  
  

  
  2
  

  
  
  
  
  
  

  
  
  As an aside, I once assessed a TLS inspection gateway product which re-signed all HTTPS connections using the internal CA, even if the remote certificate was invalid. This allowed for a particularly effective phishing campaign in which we impersonated the company intranet and had our phishing domain automagically signed by the company CA. I suggest that you check for this vulnerability yourself by trying to visit a site which you know has an invalid (e.g. expired, or incorrect domain) certificate and seeing if the connection succeeds.
  
  – Polynomial
  2 hours ago
  
  
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  
  Amazing! I feel like pen-testing is a missed calling.
  
  – Scuba Steve
  2 hours ago
  

  
  
  
  


• 
  
  
  

  
  1
  

  
  
  
  
  
  

  
  
  FWIW even if 1.3 would allow static-RSA, it changes the key derivation to include the whole handshake (not just premaster+nonces) and MITM couldn't make those equal. This is similar to rfc7627 which fixes 'triple handshake' for 1.2, except that is optional and so MITM can force it off.
  
  – dave_thompson_085
  1 hour ago
  
  
  

  
  
  
  

add a comment | 

Yes, they can MitM the traffic this way, using an internal certificate authority. There are two primary ways in which the MitM can work.

The first is to simply turn the edge gateway into a proxy, whereby TLS connections are made from the gateway to the server, and the gateway then generates server certificates on the fly from an internal CA in order to impersonate the remote server. Your system trusts the CA, so it trusts the server certificate.

The second is a slightly different take on the first. The gateway proxies the traffic similarly to the first method, except it only advertises static RSA cipher suites to the remote server. The reason for doing this is performance. With a static RSA key exchange (i.e. not Diffie-Hellman) the gateway can split the handshake as before in order to provide the client with a certificate generated via the internal CA, but instead of decrypting the content on the gateway and then re-encrypting it before proxying, it simply passes the same session key between the client and server. This way the gateway only has to decrypt the traffic once, using the captured session key, and never needs to re-encrypt it in order to proxy the traffic between client and server. This trick no longer works in TLS 1.3 as static RSA key exchange was removed.

Generally speaking this kind of TLS inspection is fairly commonplace in large organisations, particularly financials. Deploying it on BYOD devices is somewhat common, although you should consider the privacy and security implications that might arise from installing your company's internal CA certificate on your device. You need to ask yourself whether you trust that your IT security team is likely to be able to protect the signing keys, because if not then your device is liable to be MitM'ed by an attacker.

share|improve this answer

answered 2 hours ago

PolynomialPolynomial

101k31248341

share|improve this answer

answered 2 hours ago

PolynomialPolynomial

101k31248341

answered 2 hours ago

PolynomialPolynomial

101k31248341

answered 2 hours ago

PolynomialPolynomial

101k31248341