Re: [gentoo-user] Re: encrypted email (gentoo-windows)
In linux.gentoo.user, James wrote: What I would really like is to be able to exchange encrypted mail with any MS user What, you've never received an encrypted email from a windows user before? If you think about it, surely you have... I know ms is pretty bad about standards and interoperability, but pgp or gpg encrypted mail is relatively common on win, *nix, and os x. Pretty sure the problem you're trying to solve doesn't exist. -- ...she kept arranging and rearranging the rabbit and kind of waving to it. I decided, this is the person I want to sit next to.
Re: [gentoo-user] Re: encrypted email (gentoo-windows)
On Sunday 27 March 2011 03:03:30 James wrote: Sebastian Beßler sebastian at darkmetatron.de writes: Mail encryption is, as far as I know, something that works on the client-side only. The mail server doesn't see the encryption, encrypted mails contain only text, just like every other mail. OK let's ignore the mail server portion. Your basically implying that encrypted mail handling from the server, does not matter if it's an exchange server, or *nix, like postfix As an example. Look at the situation where a person is using only MS technology and has no access to support(input) on their client software nor the MS exchange server (big corp for example that assumes the world only uses MS software). Maybe they can make a few setting changes only in Outlook to get encryption working between a MS (Outlook) system and my Gentoo system using pgp and thunderbird? Depending on the MSWindows OS and email client versions your MS counterpart can try installing and running: http://www.gpg4win.org/about.html Alternatively, instead of OpenPGP you can use S/MIME certificates - either self-signed or from a aheam! reputable Certification Authority. I prefer the former where possible, although the average MSWindows user would struggle on their own to even click a (single) button, let alone generate public/private keys, configure a password and then negotiate with the MSWindows certificate manager to accept them. gpg4win will also act as the front for managing the MSWindows S/MIME certs, although Outlook can manage these for SSL signing/encryption natively. The SSL certificates offered by different CAs are mostly an expensive racket for big corporate clients. Individual users are limited to a few available CAs (like CACert, Comodo, etc) who issue free certificates for personal (email) use, but only some of the browsers include them in their store of trusted CAs - hence the need for manual import of Root CA keys, etc in the user's browser/certificate store and of course the same with the recipients of their email messages. Before you commit to a CA check which browsers and OS already included these in their trusted Root CA store. If may answer has nothing to do with your problem, please give me more information what you have in mind. I do not have a problem. I have assumed that encrypted mail between a given client software on a gentoo system, will not work with windows. Is this assumption incorrect? Yes, this is an incorrect assumption. OpenPGP will not work with MSWindows natively without a 3rd party application (e.g. gpg4win), because OpenPGP does not satisfy the requirements of Microsoft's monopolistic business model. However, SSL certificates will work natively with MSWindows and its Outlook email client. As I said above you have a choice of obtaining such certificates: self-signed or signed by trusted Root CAs (some of which are free for personal use). Also, in the era of Cloud computing you have the choice of webmail applications (like Horde) which can use both PGP and S/MIME to sign/encrypt/decrypt messages, thus bypassing limitations of given OS or desktop based mail clients. Finally, you have SaaS solutions for secure email, like http://www.hushmail.com/ but if one does not trust Root CAs why would he trust some hushmail company and its employees is beyond me. Or it's just install whatever I want (mail client on gentoo) and it will auto-magically exchange encrypted mail with outlook on a windows machine, behind a MS Exchange server, regardless of what the MS admins do on their side? Yes, as long as you manage encryption/decryption at the dekstop. You need to note though that some corporate IM policies may prohibit the use of encrypted messages. These can be filtered out by the corporate mail server and stopped. I assumed that is not that easy (my default experience with MS), and things have to be coordinated, like most MS issues, to be able to exchange encrypted mail between a gentoo and MS workstation Nothing to it, or massive issues on the MS side? Obviously, making changes on the gentoo workstation client, is easy What I would really like is to be able to exchange encrypted mail with any MS user. That, I'm sure with entail pointing them to documents on how to set up the software on the MS (outlook) side. Links for MS help? They do not need to look at Internet links - just ask them look up digital signing or encryption in their Outlook help pages. Configuring Outlook is the easy part. The more confusing part might be obtaining an S/MIME certificate and importing the Root CA certificate if it is not already included in whatever Microsoft ships with. I think that Comodo Root CA is already included (and the recently hacked Root CA certificate has not been recalled through last week's MSWindows update). ??? A general discussion at this point, not a specific solution. My googling only reveals dated
[gentoo-user] Re: encrypted email (gentoo-windows)
Mick michaelkintzios at gmail.com writes: Google has many examples and step-by-step instructions for configuring Outlook to use SSL Certs (S/MIME), usually by the purveyors of all these expensive certificate services: http://www.globalsign.com/support/personal-certificate/per_outlook07.html Hello Mick, Exactly what I was looking for. Not just the part I included, but your entire answer. Gmane get'[s fussy about including too much previous text in responses. Sure, I've set up numerous email clients, like Thunderbird and such on doze systems before (encryption or not); that's a no-brainer. Outlook in a rigid corporate environment without the admin's help on that side. interesting. If their spam filters are too aggressive, it will most likely quarantine the incoming encrypted files. A program of encryption, but makes files look like text to spam filters, would be keen, but most likely crackable, due to the limited char_set? Never tried this but hey, there is ALWAYS a way to skin the cat... But I have never tried to help an ordinary Outlook user get encryption working, so as to exchange encrypted email, with their linux bretheran without their Admin's involvement. Most admins at corps do not care, but they are understaffed and only support what they support. So you have articulated some options where I can help a generic corporate user setup and use encryption, without their admin's involvement, which I guess is what I did not clearly explain in previous posts, as the goal all along, using Outlook or other MS based applications. THANKS; for sharing your knowledge and view of the landscape. I've got it from here. James
Re: [gentoo-user] Re: encrypted email (gentoo-windows)
On Sunday 27 March 2011 15:48:53 James wrote: Mick michaelkintzios at gmail.com writes: Google has many examples and step-by-step instructions for configuring Outlook to use SSL Certs (S/MIME), usually by the purveyors of all these expensive certificate services: http://www.globalsign.com/support/personal-certificate/per_outlook07.html Hello Mick, Exactly what I was looking for. Not just the part I included, but your entire answer. Gmane get'[s fussy about including too much previous text in responses. Sure, I've set up numerous email clients, like Thunderbird and such on doze systems before (encryption or not); that's a no-brainer. Outlook in a rigid corporate environment without the admin's help on that side. interesting. If their spam filters are too aggressive, it will most likely quarantine the incoming encrypted files. A program of encryption, but makes files look like text to spam filters, would be keen, but most likely crackable, due to the limited char_set? Never tried this but hey, there is ALWAYS a way to skin the cat... But I have never tried to help an ordinary Outlook user get encryption working, so as to exchange encrypted email, with their linux bretheran without their Admin's involvement. Most admins at corps do not care, but they are understaffed and only support what they support. So you have articulated some options where I can help a generic corporate user setup and use encryption, without their admin's involvement, which I guess is what I did not clearly explain in previous posts, as the goal all along, using Outlook or other MS based applications. THANKS; for sharing your knowledge and view of the landscape. I've got it from here. Glad I could help James. :-) Before you start helping remotely MSWindows users I recommend you install MSWindows in a virtual machine (e.g. virtualbox-bin will take only a few minutes) and configure the OS and mail client to send and receive signed/encrypted messages as preferred. Otherwise, you may quickly run aground when the corporate users technical knowledge stops them configuring their machines as necessary. PS. Some corporate set ups will have the MS Windows SSL certificate store settings access blocked for normal users. In that case only MSWindows recognised S/MIME Root CAs will be usable without warnings. As far as I recall Comodo is recognised. -- Regards, Mick signature.asc Description: This is a digitally signed message part.
Re: [gentoo-user] Re: encrypted email (gentoo-windows)
Hi - if you want to be able to send encrypted email from a linux machine that a person using a windows machine can de-crypt and read securely, the simplest way is to use the Gpg4win (for the windows machine) which incorporates Claws Mail (a port of a linux email client which is also available on Gentoo). Claws mail is in Portage. So at the simplest level, if you install the Claws email on your linux box, along with a pgp encryption tool (I think it's called Gpg, not 100% sure what the Portage package is, but any pgp encryption tool will probably work, it may already be built in to Claws), then advise your windows recipients to install Gpg4win (google it) which is a windows package which includes Claws mail, you will be able to exchange encrypted emails securely between linux and windows recipients. On the windows machine, the Gpg4win package will encrypt decrypt email, you will only need to find a gpg related tool for the linux machine in order to encrypt your emails on it before sending them. I'm not really sure what gpg uses, it may well use pgp encryption which is standard and there will be a tool in Portage which can encrypt and decrypt email using pgp (or at least one to encrypt and decrypt any file which can then be forwarded by email). TBH - the encryption side of it is really OS independent, but using Gpg4win on windows and any linux email client which supports pgp encryption / signing should give you what you are looking for (Gpg=Gnu Privacy Guard). You will just need to double check that whatever you use on the linux side, is compatible with Gpg. On 27 March 2011 03:03, James wirel...@tampabay.rr.com wrote: Sebastian Beßler sebastian at darkmetatron.de writes: Mail encryption is, as far as I know, something that works on the client-side only. The mail server doesn't see the encryption, encrypted mails contain only text, just like every other mail. OK let's ignore the mail server portion. Your basically implying that encrypted mail handling from the server, does not matter if it's an exchange server, or *nix, like postfix As an example. Look at the situation where a person is using only MS technology and has no access to support(input) on their client software nor the MS exchange server (big corp for example that assumes the world only uses MS software). Maybe they can make a few setting changes only in Outlook to get encryption working between a MS (Outlook) system and my Gentoo system using pgp and thunderbird? If may answer has nothing to do with your problem, please give me more information what you have in mind. I do not have a problem. I have assumed that encrypted mail between a given client software on a gentoo system, will not work with windows. Is this assumption incorrect? Or it's just install whatever I want (mail client on gentoo) and it will auto-magically exchange encrypted mail with outlook on a windows machine, behind a MS Exchange server, regardless of what the MS admins do on their side? I assumed that is not that easy (my default experience with MS), and things have to be coordinated, like most MS issues, to be able to exchange encrypted mail between a gentoo and MS workstation Nothing to it, or massive issues on the MS side? Obviously, making changes on the gentoo workstation client, is easy What I would really like is to be able to exchange encrypted mail with any MS user. That, I'm sure with entail pointing them to documents on how to set up the software on the MS (outlook) side. Links for MS help? ??? A general discussion at this point, not a specific solution. My googling only reveals dated discussions along these lines or information that is not useful. James
Re: [gentoo-user] Re: encrypted email (gentoo-windows)
On 3/27/11 5:00 AM, Elaine C. Sharpe wrote: In linux.gentoo.user, James wrote: What I would really like is to be able to exchange encrypted mail with any MS user What, you've never received an encrypted email from a windows user before? If you think about it, surely you have... I know ms is pretty bad about standards and interoperability, but pgp or gpg encrypted mail is relatively common on win, *nix, and os x. Pretty sure the problem you're trying to solve doesn't exist. Outlook uses S/MIME rather than PGP. If this user is used to being part of a normal Windows domain infrastructure with PKI and they haven't set up their system properly then it would appear that they cannot exchange encrypted mail with an MS user. signature.asc Description: OpenPGP digital signature
[gentoo-user] Re: encrypted email (gentoo-windows)
Sebastian Beßler sebastian at darkmetatron.de writes: Mail encryption is, as far as I know, something that works on the client-side only. The mail server doesn't see the encryption, encrypted mails contain only text, just like every other mail. OK let's ignore the mail server portion. Your basically implying that encrypted mail handling from the server, does not matter if it's an exchange server, or *nix, like postfix As an example. Look at the situation where a person is using only MS technology and has no access to support(input) on their client software nor the MS exchange server (big corp for example that assumes the world only uses MS software). Maybe they can make a few setting changes only in Outlook to get encryption working between a MS (Outlook) system and my Gentoo system using pgp and thunderbird? If may answer has nothing to do with your problem, please give me more information what you have in mind. I do not have a problem. I have assumed that encrypted mail between a given client software on a gentoo system, will not work with windows. Is this assumption incorrect? Or it's just install whatever I want (mail client on gentoo) and it will auto-magically exchange encrypted mail with outlook on a windows machine, behind a MS Exchange server, regardless of what the MS admins do on their side? I assumed that is not that easy (my default experience with MS), and things have to be coordinated, like most MS issues, to be able to exchange encrypted mail between a gentoo and MS workstation Nothing to it, or massive issues on the MS side? Obviously, making changes on the gentoo workstation client, is easy What I would really like is to be able to exchange encrypted mail with any MS user. That, I'm sure with entail pointing them to documents on how to set up the software on the MS (outlook) side. Links for MS help? ??? A general discussion at this point, not a specific solution. My googling only reveals dated discussions along these lines or information that is not useful. James
