Questions tagged [smime]

S/MIME is a protocol for signing and/or encrypting emails using certificates

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Do expired, revoked, self-signed S/MIME certificates trigger email SPAM filters or affect mail delivery?

For example, I have an expired or revoked S/MIME certificate. Can I sign or can the recipient encrypt a message with it? Will an email client allow it? If it is possible, will the message be rejected ...
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1answer
35 views

Is the private key for S/MIME certificates generated on the CA servers or in the browser?

I heard that some certificate authorities generate your private key for S/MIME certificates on their servers. However, some of them who recommend using Internet Explorer for this purpose, probably, ...
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1answer
44 views

How is outgoing email encrypted by S/MIME certificates?

After several hours of surfing the internet, I failed to find any comprehensive guide on how to encrypt the email between two users using the S/MIME certificate. In parallel with SSL certificates: ...
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How is the signature of an email S/MIME certificate verified?

To my knowledge, the signature of an SSL certificate is verified by the public keys of root certificates that are installed in the browser certificate storage. How are signatures of the S/MIME ...
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S/MIME Certificate has expired and I am unable to Re-Issue

Screenshot of Certificates Snap-in (Local Computer) Screenshot of GPO Hello, I have a Windows Server 2012 R2 machine that is our internal CA server. I have a GPO to push a Secure Email certificate ...
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1answer
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Outlook sMIME certificates location, errors, and background work

We have an situation. Our customer can get sMIME encrypted mails and reply to that email. But when he wants to send it with new email he is getting an error message as if the recipient email does not ...
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1answer
322 views

Cannot recover backup made with `openssl smime`

My (only) database server went down and I am in the process of recovering everything. I created a new server and now I just want to restore the database backup. I have a nightly script that runs this ...
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1answer
230 views

Digital Signature is not valid

I recently received a digital signed email from a friend and the certificate is issued by COMODO RSA Client Authentication and Secure Email. My problem is the thunderbird detect it as a "Not Valid ...
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1answer
426 views

What are the best practices for providing S/MIME-Certificates in Outlook?

I got some questions regarding S/MIME in Outlook and certificates in general. Some questions arrised about the possibility to digitally sign emails in my company. As I'm new to the topic I had to do ...
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1answer
268 views

Scan S/MIME Encrypted Email on Exchange Server

We have a copy of each user's S/MIME encryption (well, decryption) private keys as well as their certificate centrally managed in an HSM. We want to configure Exchange to automatically decrypt any ...
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1answer
785 views

How can I select a certificate from a PEM file with multiple certificates?

Background info: I am working on an OS X server, and I need to use certificates from the key chain with openssl smime in order to encrypt messages in a bash script. In order to do so, I use the ...
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1answer
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Email signing using commercial SSL certificate

I am considering securing my work environment with certificates and thus have a couple of questions. My Active Directory domain is domain.com. If I buy a commercial wildcard SSL certificate from i.e. ...
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1answer
3k views

Verifying S/MIME signed message with OpenSSL without checking the certificate's purpose

The problem: When I sign a message with a certificate which is used for a HTTPS webserver, OpenSSL does not want to verify it back. Signing a message: echo "TestMessage" | openssl smime \ -sign ...
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1answer
2k views

AD Certificate template - Enroll on behalf of

I'm trying to setup S/MIME for a few users, which requires certificates. I'm not using smartcards, and not using autoenrollment for these certificates. Server is running 2012R2. I created a ...
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2answers
309 views

openssl smime message signing: why do I need a -certfile key?

Here is how one should sign a message with openssl smime? according to the docs openssl smime -sign -in in.txt -text -out mail.msg -signer mycert.pem \ -inkey mykey.pem -certfile mycerts.pem But ...
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1answer
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Generating public/private credentials for MS Outlook email encryption

An app running on a CentOS 7 web server needs to receive encrypted emails sent from users of MS Outlook. Can someone please provide explicit instructions as to how I can generate or procure all of ...
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1answer
465 views

Smart Card S/MIME with Exchange 2013

I have an Exchange 2013 environment that I'm trying to implement S/MIME with smart cards. To the best of my knowledge, and the little help I have received on TechNet, I have configured my Exchange ...
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1answer
2k views

Automatic S/MIME certificate distribution/outlook integration for signed/encrypted email

I have a Windows Server 2008 R2 Machine and an Exchange 2010 Server on two seperate machines. The WS2008R2 machine is configured with a certificate authority in which I have configured certificate ...
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1answer
710 views

S/MIME: signed mails with disclaimer from mail filter/mailscanner?

We have a Mailscanner, which scans incoming and outgoing mails and add a small disclaimer (Mail was checked for Viruses... bla bla bla). So far i can add a disclaimer without signing the mail, or ...
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0answers
341 views

Are External LDAP referrals similar to a DNS Recursive or non recursive entry?

I'm very familiar with DNS, but less so with LDAP. In DNS I have the ability to delegate the CPU and IO load of referral chasing a given DNS query... or I can set norecurse and have the client ...
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1answer
433 views

How can I limit the SMIME capabilities from a CA without using FIM?

These instructions describe how to prevent using SMIME with weak ciphers, however it requires an expensive product from Microsoft. How can I prevent a CA from issuing SMIME certificates that permit ...
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1answer
344 views

Possible to make SMIME signatures not appear as an attachment? (e.g. in Gmail)

We are using SMIME across our organisation and are getting complaints that the SMIME signature is appearing as an attachment in various email clients. (gmail) Is there any way to edit the SMTP ...
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2answers
2k views

Is it generally acceptable to expose LDAP in read only mode to the Internet?

I need to support Mac clients who need to access a LDAP server to locate SMIME keys. Since the keys are already in AD, and it's easy for me to create a RODC or read only forest where I push the ...
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1answer
2k views

S/MIME icon missing from OWA

I'm trying to test S/MIME with OWA (Exchange 2010, Outlook 2010). Now my research has told me that the control must be installed first. So as someone with admin rights, open OWA, click on All Option, ...
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1answer
2k views

How do I configure AD CS to support Name Constraints (4.2.1.11 in RFC 2459)?

I am trying to figure out how to do Qualified Subordination with the critical extension set, but I'm unable to figure out how to do this in MSFT AD CS. For a given certificate, how do I make sure ...
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546 views

How to setup an openldap addressbook for thunderbird secure s/mime email ?

I want to setup an ldap server that will hold an addressbook of users their emails their smime certificates. I want to use this ldap server as an addressbook in thunderbird and/or other mail clients ...
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1answer
8k views

Sign outgoing mails automatically with postfix (S/MIME)

I want to sign outgoing mails automatically with postfix. I've found a script and integrated it into postfix. That works mostly like expected, but it has two bugs and I hope you can help me to fix ...
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2answers
445 views

How can I confirm which specific S/MIME public key was used to encrypt an email?

CentOS 5.8 Is there an easy way to tell what specific public key was used to encrypt an email? My email gateway isn't able to decrypt an inbound S/MIME message and I'm suspecting that the remote ...
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0answers
196 views

mutt, smime, decrypt with one of two different keys

This is an odd one. We want to have an encrypted e-mail list. There are a few ways to do this, but in the interim what we've done is created a public/private keypair via openssl for our e-mail list (...
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2answers
156 views

Is there a way to make encryption default per contact in Thunderbird?

I administer several computers that have Thunderbird installed. I know Thunderbird has an option to require all email to be encrypted. However, I would like a way to allow unencrypted email normally,...
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3answers
3k views

Outlook Encrypted Emails boo boo

I just reinstalled my Windows OS 7 and forgot to backup my Email Certificate for Outlook 2010 beforehand. Now I can't read any encrypted emails. When I try, it says "Cannot open this item. Your ...
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2answers
1k views

Can I configure mailman so that it won't break S/MIME digital signatures?

We're currently using Mailman as a mailing list manager. Mailman modifies the content of mail messages. The problem is that some of our users are sending digitally signed messages and the modification ...
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1answer
170 views

Secure e-mail with SMTP Virtual Server in Windows 2008

Is it possible to send encrypted and digitally signed e-mail messages using S/MIME through the SMTP Virtual Server component included in Windows Server 2008 or do I have to use Exchange? If it is, ...
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2answers
2k views

Any web email providers that support sending and receiving S/MIME encrypted email? [closed]

Can anyone suggest a webmail provider (like gmail, Yahoo mail, hotmail, etc.) that supports S/MIME encrypted email well? Both sending and receiving email and obviously keeping track of the encryption ...