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Questions tagged [smime]

S/MIME (Secure/Multipurpose Internet Mail Extensions) is a standard for public key encryption and signing of MIME data. Its role is similar to PGP.

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Exchange 2010 Transport Rule with S/MIME

If we create a transport rule to block all emails sending out with .doc attachment, it seems that the rule won't work on email which is signed with S/MIME cert. The email sending out is just signed, ...
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1answer
93 views

Sending an encrypted and digitally signed email from Outlook to other webmail clients

The company I work for uses Microsoft Exchange 2016 for email and we have S/MIME certificates for email encryption and digital signatures. Encryption and signing works for other exchange users, but is ...
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22 views

Make macOS Mail.app to attach full certificate chain to mail

When I'm sending S/MIME mails from Microsoft Outlook, it attaches the full certificate chain to the out-going mail so that recipients can verify the signing key (similar to how TLS works). However, ...
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102 views

Decrypt CMS (former S/MIME) Mail with OpenSSL including the E-Mail Header

I encrypt mails via a Sophos UTM and on a Linux machine with OpenSSL I want to decrypt these mails. With the command openssl cms -decrypt -in mail.msg -recip mycert.pem -inkey key.pem mail_enc.msg ...
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323 views

Can not decrypt encrypted S/MIME message

After I sent an S/MIME signed eMail to an insurance company, their exchange server picked up my S/MIME certificate and their reply was S/MIME encrypted. Before, they used my PGP public key to encrypt ...
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1answer
723 views

S/MIME signed email loses attachment

We have a small number of users who digitally sign (but don't encrypt) their email. When they send attachments, it usually works fine. However, when the recipient is using Outlook Mobile, all ...
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1answer
47 views

Make OS-X Mail to choose a certain certificate for S/MIME signature

I have been using Apple Mail and S/MIME for quite a while now. While I have been starting with a commercial certificate, I now decided to switch to a certificate from a dedicated CA (recognized by all ...
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1answer
3k views

How to decrypt an S/MIME encrypted email using openssl smime?

For some reason, I seem unable to find an answer to this basic question. I have received an encrypted S/MIME email, and I want to decrypt it using openssl smime. However, I assume I am unable to ...
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1answer
494 views

Outlook 2016 answering a signed (S/MIME) email does not work

I have an outlook with 2 email addresses. One is an exchangeaccount and one is gmail. The exchange one uses a S/MIME certificate to sign outgoing emails. The gmail one doesn't use the certificate. ...
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1answer
413 views

Create Intermediate CA that can issue Certificates?

I'm trying to create a CA and Intermediate CA for use in Office 365 signing/encryption purposes in Outlook. I've been able to follow a bunch of tutorials and with OpenSSL produce a CA and Intermediate ...
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1answer
200 views

how to use / import a Lotus Notes public key into Thunderbird

A colleague from abroad who uses Lotus Notes sent me his "internet certificate" (i.e. public key), so I could import it into my own e-mail client. Unfortunately I do not recognise the format (neither ...
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1answer
633 views

Outlook 2016 freezes when sending SMIME signed messages

I have an Outlook 2016 instance linked to a Microsoft Exchange 2013 server, running on a Windows 2016 Standard Remote Desktop Server. Everything works fine, just when I send a S/MIME signed message, ...
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1answer
483 views

Outlook warns about expired sender certificate that wasn't expired when sending S/MIME mail

When opening an email that was signed with a certificate which is since expired, Outlook 2007 warns that the signature is "invalid or not trusted" (shown in German as "ungültig oder nicht ...
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2answers
2k views

Outlook 2016: Multiple accounts, certificates only for one

This question has ben asked before but yet never answered. I have set up my Outlook 2016 with three different Mail accounts: name@domain1.com (commertial, office365) name@hotmail.com (personal, ...
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1answer
3k views

How to decrypt a broken S/MIME message sent by Outlook?

Recently, I received an encrypted message sent by Outlook which I cannot decrypt. Thunderbird is printing following error message instead: Thunderbird cannot decrypt this message The sender ...
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2answers
767 views

How to encrypt E-Mails with S/MIME

I am considering to encrypt some of my mails using S/MIME v3.1, since my devices should support it. Now I wonder if there is a (command line) tool that could do that for me? I tried to google it, ...
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2answers
431 views

Lotus Notes: issue when import Symantec/Verisign certificate

In order to sign/encrypt Email I have installed Verisign S-Mime Certificate from Verisign and exported it from IE as a .pfx (PKCS #12). My problem is when I tried to import it in Security > My ...
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1answer
566 views

Outlook S/MIME certificate expiration

I am using a certificate in Outlook to encrypt and sign messages. Everything work great. My certificate is going to expire next year. The following is unclear to me: Should I get a new certificate, ...
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1answer
198 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
496 views

S/MIME with GMail in Browser

So I have a S/MIME Certificate at StartSSL now. I can now use it in my Thunderbird on Ubuntu and Windows 7. But how can I configure my Browser(Chrome) to use my certificate(which is already imported ...
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1answer
220 views

Possible to change Outlook SMIME icon from RED to Blue?

Every SMIME clear signed message has a red icon located near the Urgent exclamation point as shown below. This is often confused with high priority, and sends the wrong subtle message. IMHO a red ...
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1answer
1k views

Signing-milter / SMIME - how are this email signed incorrectly?

I have a problem with signing-milter (http://www.signing-milter.org). The problem is that the -b flag is required, and the -b flag is not recommended because it outputs non-RFC compliant email. ...
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1answer
446 views

S/MIME for Mac and iOS

I have been trying to generate S/MIME certificates for my MacOS and iOS devices and it does not seem to work. I have researched on this matter and it seems that keyUsage and extendedKeyUsage are ...
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3answers
5k views

How to get GPG working with Outlook 2013?

My OS is Windows 8.1 Update 1 x64. I have Outlook 2013 and just installed GPG4Win (latest, 2.2.2, full version). When I now launch Outlook 2013, I still don't see any UI/options to setup certificates ...
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1answer
6k views

OS X 10.10 Apple Mail not recognizing S/MIME certificate

After upgrading to Yosemite, Apple Mail no longer recognizes my S/MIME certificate. This was working in Mavericks. I've checked Keychain and the certificate is valid, even evaluated it as S/MIME for ...
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1answer
135 views

How can I add an LDAP directory to all Outlook profiles? (SMIME directory)

I need my Windows based Outlook users to be able to look up an SMIME certificate from this LDAP directory How can I automatically (via scripting or policy) modify an Outlook profile to include this?
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189 views

Emacs Gnus email decrypt smime without openssl

I use gnus for my email. Every once in a while, I receive an encrypted email; when I answer "yes" to Gnus offer to decrypt it, it responds smime-verify-region: No CA configured. Now, my workplace ...
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0answers
436 views

Outlook 2013: Multiple accounts, sign only mails from one account

I have two email accounts (Exchange) configured in Outlook. For one I have a S/MIME certificate configured which always signs the mails I send from this account. Problem now is that Outlook also ...
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1answer
660 views

Is it possible to use self-signed SMIME certs with Mutt?

I'm trying to use a self-signed SMIME key that my company has issued me with Mutt. However, when I try to import it with smime_keys I get the following. Couldn't identify root certificate! No root ...
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1answer
4k views

Can't S/MIME sign using OpenSSL even if “verify” suceeds

I have a client certificate in Chrome, that I used for logging into StartSSL. I exported it using pk12util to certfile.p12. Now I want to use it for signing with S/MIME. I converted the p12 file to ...
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1answer
178 views

Can I sign my emails with both S/MIME and PGP/GPG?

And if it possible, is there any benefit from doing so in one order or the other? signWithSMIME(signWithPGP(message)) versus signWithPGP(signWithSMIME(message)) Also, are there any reason not to ...
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0answers
1k views

S/MIME email Public Certificate?

Is there a way to create a public certificate for a S/MIME email certificate? I would like to share the public key on my website so people can send me encrypted emails. However I can only find "...
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1answer
187 views

How does Outlook deal with temporary data encrypted with S/MIME?

We are using S/MIME to encrypt messages and their attachments and Outlook as email application. All documents sent in attachment are stored on an encrypted folder and should never be copied anywhere ...
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1answer
3k views

Any way to sign mails in Gmail with S/MIME?

i am using S/MIME to sign my mails in Thunderbird and Apple Mail on my iOS devices. But from time to time i also use the Gmail webmailer. Is there any working pluging for Mozilla Firefox to also sign ...
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0answers
54 views

Mailinglists in Thunderbird with S/MIME

I am looking for a solution to send encrypted mails to a (internal) mailinglist. To encrypt the mail to all the recipients, I need some way to tell Thunderbird what the recipients are. I was hoping ...
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1answer
621 views

Does SMIME encrypt the subject matter?

I've recently acquired an SMIME certificate and installed it in Outlook 2013. I set my brother up to do the same. So I used his certificate to send him an encrypted mail. He had an out of office ...
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2answers
6k views

Outlook 2013, multiple email accounts and encrypted email: Only last S/MIME settings used

I have multiple email accounts properly setup in Outlook 2013 (can send/receive fine otherwise). Lets say they are: user1@domain1.com user2@domain2.com user3@domain3.com All belong to me and I have ...