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The misconception that you're having is that security through obscurity is bad. It's actually not, security only through obscurity is terrible.

Put it this way. You want your system to be complete secure if someone knew the full workings of it, apart from the key secret component that you control. Cryptography is a perfect example of this. If you are relying on them 'not seeing your algorithm' by using something like a ROT13 cipher it's terrible. On the flip side if they can see exactly the algorithm used yet still cannot practically do anything we see the ideal security situation.

The thing to realize is that you never want to count on obscurity but it certainly never hurts. Should I password protect / use keys for my SSH connection? Absolutely. Should I rely on changing the server from 22 to port 2222 to keep my connection safe? Absolutely not. Is it bad to change my SSH server to port 2222 while also using a password? No, if anything this is the best solution. Changing ("Obscuring") the port will simply cut down on a heap of automatic exploit scanners searching normal ports. We gain a security advantage through obscurity which is good, but we are not counting on the obscurity. If they found it they still need to crack the password.

TL;DR - Only counting on obscurity is bad. You want your system to be secure with the attacker knowing it's complete workings apart from specifically controllable secret information (i.e. passwords). Obscurity in itself however isn't bad, and can actually be a good thing.

Edit: To more precisely answer your probability question, yes in a way you could look at it like that, yet do so appreciating the differences. Ports range from 1-65535 and can be quickly checked within 1 minute with a scanner like nmap. "Guessing" a random say 10 digit password of all ascii characters is 1 / 1.8446744e+19 and would take 5.8 million years guessing 100,000 passwords a second.

Edit 2: To address the comment below. Keys can be generated with sufficient entropy to be considered truly random (http://tools.ietf.org/html/rfc4086). If not it's a flaw with the implementation rather than the philosophy. You're correct in saying that everything relies on attackers not knowing information (passwords) and the dictionary definition of obscurity is "The state of being unknown", so you can correctly say that everything is counting on a level of obscurity.

Once more though the worth comes down to the practical security given the information you're able to control remaining unknown. Keys, be it passwords or certificates etc, are (relatively) simple to maintain secret. Algorithms and other easy to check methods are hard to keep secret. "Is it worth while" comes down to determining what is possible to keep unknown, and judging the possibility of compromise based off that unknown information.

The misconception that you're having is that security through obscurity is bad. It's actually not, security only through obscurity is terrible.

Put it this way. You want your system to be complete secure if someone knew the full workings of it, apart from the key secret component that you control. Cryptography is a perfect example of this. If you are relying on them 'not seeing your algorithm' by using something like a ROT13 cipher it's terrible. On the flip side if they can see exactly the algorithm used yet still cannot practically do anything we see the ideal security situation.

The thing to realize is that you never want to count on obscurity but it certainly never hurts. Should I password protect / use keys for my SSH connection? Absolutely. Should I rely on changing the server from 22 to port 2222 to keep my connection safe? Absolutely not. Is it bad to change my SSH server to port 2222 while also using a password? No, if anything this is the best solution. Changing ("Obscuring") the port will simply cut down on a heap of automatic exploit scanners searching normal ports. We gain a security advantage through obscurity which is good, but we are not counting on the obscurity. If they found it they still need to crack the password.

TL;DR - Only counting on obscurity is bad. You want your system to be secure with the attacker knowing it's complete workings apart from specifically controllable secret information (i.e. passwords). Obscurity in itself however isn't bad, and can actually be a good thing.

Edit: To more precisely answer your probability question, yes in a way you could look at it like that, yet do so appreciating the differences. Ports range from 1-65535 and can be quickly checked within 1 minute with a scanner like nmap. "Guessing" a random say 10 digit password of all ascii characters is 1 / 1.8446744e+19 and would take 5.8 million years guessing 100,000 passwords a second.

The misconception that you're having is that security through obscurity is bad. It's actually not, security only through obscurity is terrible.

Put it this way. You want your system to be complete secure if someone knew the full workings of it, apart from the key secret component that you control. Cryptography is a perfect example of this. If you are relying on them 'not seeing your algorithm' by using something like a ROT13 cipher it's terrible. On the flip side if they can see exactly the algorithm used yet still cannot practically do anything we see the ideal security situation.

The thing to realize is that you never want to count on obscurity but it certainly never hurts. Should I password protect / use keys for my SSH connection? Absolutely. Should I rely on changing the server from 22 to port 2222 to keep my connection safe? Absolutely not. Is it bad to change my SSH server to port 2222 while also using a password? No, if anything this is the best solution. Changing ("Obscuring") the port will simply cut down on a heap of automatic exploit scanners searching normal ports. We gain a security advantage through obscurity which is good, but we are not counting on the obscurity. If they found it they still need to crack the password.

TL;DR - Only counting on obscurity is bad. You want your system to be secure with the attacker knowing it's complete workings apart from specifically controllable secret information (i.e. passwords). Obscurity in itself however isn't bad, and can actually be a good thing.

Edit: To more precisely answer your probability question, yes in a way you could look at it like that, yet do so appreciating the differences. Ports range from 1-65535 and can be quickly checked within 1 minute with a scanner like nmap. "Guessing" a random say 10 digit password of all ascii characters is 1 / 1.8446744e+19 and would take 5.8 million years guessing 100,000 passwords a second.

Edit 2: To address the comment below. Keys can be generated with sufficient entropy to be considered truly random (http://tools.ietf.org/html/rfc4086). If not it's a flaw with the implementation rather than the philosophy. You're correct in saying that everything relies on attackers not knowing information (passwords) and the dictionary definition of obscurity is "The state of being unknown", so you can correctly say that everything is counting on a level of obscurity.

Once more though the worth comes down to the practical security given the information you're able to control remaining unknown. Keys, be it passwords or certificates etc, are (relatively) simple to maintain secret. Algorithms and other easy to check methods are hard to keep secret. "Is it worth while" comes down to determining what is possible to keep unknown, and judging the possibility of compromise based off that unknown information.

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The misconception that you're having is that security through obscurity is bad. It's actually not, security only through obscurity is terrible.

Put it this way. You want your system to be complete secure if someone knew the full workings of it, apart from the key secret component that you control. Cryptography is a perfect example of this. If you are relying on them 'not seeing your algorithm' by using something like a ROT13 cipher it's terrible. On the flip side if they can see exactly the algorithm used yet still cannot practically do anything we see the ideal security situation.

The thing to realize is that you never want to count on obscurity but it certainly never hurts. Should I password protect / use keys for my SSH connection? Absolutely. Should I rely on changing the server from 22 to port 2222 to keep my connection safe? Absolutely not. Is it bad to change my SSH server to port 2222 while also using a password? No, if anything this is the best solution. Changing ("Obscuring") the port will simply cut down on a heap of automatic exploit scanners searching normal ports. We gain a security advantage through obscurity which is good, but we are not counting on the obscurity. If they found it they still need to crack the password.

TL;DR - Only counting on obscurity is bad. You want your system to be secure with the attacker knowing it's complete workings apart from specifically controllable secret information (i.e. passwords). Obscurity in itself however isn't bad, and can actually be a good thing.

Edit: To more precisely answer your probability question, yes in a way you could look at it like that, yet do so appreciating the differences. Ports range from 1-65535 and can be quickly checked within 1 minute with a scanner like nmap. "Guessing" a random say 10 digit password of all ascii characters is 1 / 1.8446744e+19 and would take 5.8 million years guessing 100,000 passwords a second.

The misconception that you're having is that security through obscurity is bad. It's actually not, security only through obscurity is terrible.

Put it this way. You want your system to be complete secure if someone knew the full workings of it, apart from the key secret component that you control. Cryptography is a perfect example of this. If you are relying on them 'not seeing your algorithm' by using something like a ROT13 cipher it's terrible. On the flip side if they can see exactly the algorithm used yet still cannot practically do anything we see the ideal security situation.

The thing to realize is that you never want to count on obscurity but it certainly never hurts. Should I password protect / use keys for my SSH connection? Absolutely. Should I rely on changing the server from 22 to port 2222 to keep my connection safe? Absolutely not. Is it bad to change my SSH server to port 2222 while also using a password? No, if anything this is the best solution. Changing ("Obscuring") the port will simply cut down on a heap of automatic exploit scanners searching normal ports. We gain a security advantage through obscurity which is good, but we are not counting on the obscurity. If they found it they still need to crack the password.

TL;DR - Only counting on obscurity is bad. You want your system to be secure with the attacker knowing it's complete workings apart from specifically controllable secret information (i.e. passwords). Obscurity in itself however isn't bad, and can actually be a good thing.

The misconception that you're having is that security through obscurity is bad. It's actually not, security only through obscurity is terrible.

Put it this way. You want your system to be complete secure if someone knew the full workings of it, apart from the key secret component that you control. Cryptography is a perfect example of this. If you are relying on them 'not seeing your algorithm' by using something like a ROT13 cipher it's terrible. On the flip side if they can see exactly the algorithm used yet still cannot practically do anything we see the ideal security situation.

The thing to realize is that you never want to count on obscurity but it certainly never hurts. Should I password protect / use keys for my SSH connection? Absolutely. Should I rely on changing the server from 22 to port 2222 to keep my connection safe? Absolutely not. Is it bad to change my SSH server to port 2222 while also using a password? No, if anything this is the best solution. Changing ("Obscuring") the port will simply cut down on a heap of automatic exploit scanners searching normal ports. We gain a security advantage through obscurity which is good, but we are not counting on the obscurity. If they found it they still need to crack the password.

TL;DR - Only counting on obscurity is bad. You want your system to be secure with the attacker knowing it's complete workings apart from specifically controllable secret information (i.e. passwords). Obscurity in itself however isn't bad, and can actually be a good thing.

Edit: To more precisely answer your probability question, yes in a way you could look at it like that, yet do so appreciating the differences. Ports range from 1-65535 and can be quickly checked within 1 minute with a scanner like nmap. "Guessing" a random say 10 digit password of all ascii characters is 1 / 1.8446744e+19 and would take 5.8 million years guessing 100,000 passwords a second.

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The misconception that you're having is that security through obscurity is bad. It's actually not, security only through obscurity is terrible.

Put it this way. You want your system to be complete secure if someone knew the full workings of it, apart from the key secret component that you control. Cryptography is a perfect example of this. If you are relying on them 'not seeing your algorithm' by using something like a ROT13 cipher it's terrible. On the flip side if they can see exactly the algorithm used yet still cannot practically do anything we see the ideal security situation.

The thing to realize is that you never want to count on obscurity but it certainly never hurts. Should I password protect / use keys for my SSH connection? Absolutely. Should I rely on changing the server from 22 to port 2222 to keep my connection safe? Absolutely not. Is it bad to change my SSH server to port 2222 while also using a password? No, if anything this is the best solution. Changing ("Obscuring") the port will simply cut down on a heap of automatic exploit scanners searching normal ports. We gain a security advantage through obscurity which is good, but we are not counting on the obscurity. If they found it they still need to crack the password.

TL;DR - Only counting on obscurity is bad. You want your system to be secure with the attacker knowing it's complete workings apart from specifically controllable secret information (i.e. passwords). Obscurity in itself however isn't bad, and can actually be a good thing.