Mail.app: Self-Signed SSL Certificates

How can I make mail trust self signed mail certificates FOREVER? As it is now, I have to tell Mail.app to always trust the cert for each email account, every time I launch mail. Then it remembers to trust it until I quit mail, then I have to re-tell it all over again. This is bearable on my desktop but on my laptop, where I need SSL the most, I'm constantly logging in and out and rebooting, and it drives me crazy.
FYI it's my own server, running Mac OS X Server. And I'm not buying a certificate, it's the encryption I'm after

First, the certificate must match the name Incoming Mail Server that your clients are using. For example 'mail.acme.com'. So, when creating the self-signed certificate, the common name that you enter would be 'mail.acme.com'. If you don't do this, you will always be prompted about the certificate when you relaunch Apple mail.
Just for clarification, here is how you should trust the self-signed certificate on the Macs that are using Apple Mail:
1. When you get the prompt about the certificate, click the show certificate button.
2. Drag the icon of the Certificate on the left in the Show Certificate dialog box to the desktop. This will create a document on your desktop named 'mail.acme.com.cer'.
3. Double click the certificate on the desktop which will open an Add Certificate dialog box.
4. Depending on the version of Mac OS X that you are running, what you do next will vary a little.
Leopard
1. Click the drop down next to keychain and select System
2. Open Keychain Access (Applications/Utilities) if it is not already open
3. Click System on left hand side under Keychains
4. Locate the 'mail.acme.com' certificate on the right and double-click it to open it. (NOTE: I had to quit Keychain Access and reopen it before the certificate showed up under System for me for some odd reason)
5. Click the gray triangle next to Trust to expand the Trust section of the Certificate.
6. Select Always Trust from the drop down next to 'When using this certificate'
7. Close the certificate window and then quit out of Keychain Access
8. Click the continue button back in Apple Mail if the Certificate dialog is still present.
9. Quit out of Apple Mail and the relaunch it again. This time you should not see the certificate dialog alert.
Tiger
1. Click the drop down next to keychain and select X509Anchors
2. Open Keychain Access (Applications/Utilities) if it is not already open
3. Click System on left hand side under Keychains
4. Locate the 'mail.acme.com' certificate on the right and double-click it to open it.
5. Click the gray triangle next to Trust to expand the Trust section of the Certificate.
6. Select Always Trust Settings from the drop down next to 'When using this certificate'
7. Close the certificate window and then quit out of Keychain Access
8. Click the continue button back in Apple Mail if the Certificate dialog is still present.
9. Quit out of Apple Mail and the relaunch it again. This time you should not see the certificate dialog alert.
This worked for me. I hope this works for you too.

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E-Mail Setup fails with self-signed SSL certificat...

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Any one around who can help? Self-Signed certificates are rather common, after all. I would be grateful cave

Abandoning Self-Signed SSL Certificates?

Hello,
I'm working on remediation of some security flaws and have encountered a finding that calls out each of my domain-added workstations as having self signed SSL certificates. I'm not an expert on the subject, but I do know the following things:
1) An earlier finding lead to me disabling all forms of SSL on my servers and workstations
2) Workstations use certificates to identify themselves to other domain assets.
Now my servers all have their own certs signed by an outside authority. However, it would be a huge amount of work to go through the process for each and every workstation. So my questions are these:
1) Can I create a NON-SSL self signed cert for these machines to use?
2) How do I remove these current SSL certs without having to hover over each workstation?
Basically, what's the least effort to remove self-signed SSL certs and replace them with something more secure?
Thanks,
M.

What do you mean when you say that you've disabled all forms of SSL on your servers and workstations? SSL serves to provide secure communications for all of your domain operations, so disabling SSL, in general, would likely break your entire domain. If you're
using certificates on your workstations, then you're using certificate-based security (IPSec) in some manner.
Do you have AD CS or some other certificate signing authority/PKI in your environment? If not, you would have to pay a public provider (i.e. VeriSign) to provide certificates, and I can assure you that gets very expensive.
If you have Microsoft servers in your environment, you can install and use Certificate Services to provide an internal signing mechanism which can be managed through group policy. You can replace all of the workstation certificates with ones signed by your
internal certificate authority (CA,) and those will pass muster with any auditor provided the appropriate safeguards are put into place elsewhere in your environment.
Least effort for you would be to implement an internal CA, which admittedly isn't a low-effort endeavor, and have the CA assign individual certificates to all of your machines, users, and any other assets you need to protect. If your auditors are requiring
the removal of the self-signed certificates, you might find a way to script the removal of the certificates. In my experience, however, most auditors just want IPSec to be done with certificates that terminate somewhere other than the local workstation (i.e.
an internal CA).

IPhone LDAP contacts and Self signed SSL certificates

Hi,
I am using OpenLDAP with self signed SSL certificate, and i am unable to get SSL work with LDAP contacts on the IPhone (4.x). I have tried to add a CA cert with a server certificate for the LDAP server and downloaded it to the IPhone by web, it adds the CA, but even with it, it does not want to connect to the LDAP server with SSL enabled.
Does LDAP contacts should work by adding new CA ? if yes, what is the exact procedure to do it ? (maybe I used a wrong CA export format, or wrong SSL certificate encryption format ...)
can someone tell me how to do it ?
This is really anoying, since we have multiple iphones on the company.
Thanks for the help.

Hello, found your post. I realize it's been 6 months since you posted, but I have a solution for you since I have struggled with the same problem since 2009.
I discovered that when the iPhone is using LDAPS, it tries to bind with LDAPv2. After it binds, it speaks LDAPv3 like it is supposed to. Apparently this is a somewhat common practice since OpenLDAP includes an option for it.
You'll want to set the following option in OpenLDAP:
dn: cn=config
olcAllows: bind_v2
Walla! LDAPS works! (assuming you've correctly done all the certificate stuff). Took some deep reading through the debug logs to figure out this problem. Figured I'd share my answer with others.

Extend self-signed SSL certificate beyond one year

Hi all,
How can I extend SSL Certificate created by Windows 2008 R2's Certificate Service beyond 1 year?
Thanks.

Hi,
For self-signed certificate, you can use IIS Manager to create new one. For more detailed steps, please refer to the below steps.
Create a Self-Signed Server Certificate in IIS 7
http://technet.microsoft.com/library/cc753127(WS.10)
If it’s a certificate issued by a CA, we just need to renew the certificate with the CA to extend the valid date.
Best Regards,
Aiden
Aiden Cao
TechNet Community Support

How do I install this self-signed SSL certificate?

I haven't been able to connect to the jabber server I've been using (phcn.de) for quite some time now, so I filed a bug report with mcabber. The friendly people there told me to install phcn.de's self-signed certificate, but I can't figure out for the life of me how to do that.
I know I can download something resembling a certificate using
$ gnutls-cli --print-cert -p 5223 phcn.de
Which does give me something to work with:
Resolving 'phcn.de'...
Connecting to '88.198.14.54:5223'...
- Ephemeral Diffie-Hellman parameters
- Using prime: 768 bits
- Secret key: 767 bits
- Peer's public key: 767 bits
- PKCS#3 format:
-----BEGIN DH PARAMETERS-----
MIHFAmEA6eZCWZ01XzfJf/01ZxILjiXJzUPpJ7OpZw++xdiQFBki0sOzrSSACTeZ
hp0ehGqrSfqwrSbSzmoiIZ1HC859d31KIfvpwnC1f2BwAvPO+Dk2lM9F7jaIwRqM
VqsSej2vAmAwRwrVoAX7FM4tnc2H44vH0bHF+suuy+lfGQqnox0jxNu8vgYXRURA
GlssAgll2MK9IXHTZoRFdx90ughNICnYPBwVhUfzqfGicVviPVGuTT5aH2pwZPMW
kzo0bT9SklI=
-----END DH PARAMETERS-----
- Certificate type: X.509
- Got a certificate list of 1 certificates.
- Certificate[0] info:
- subject `CN=phcn.de', issuer `CN=phcn.de', RSA key 1024 bits, signed using RSA-SHA, activated `2009-05-04 08:26:21 UTC', expires `2014-04-08 08:26:21 UTC', SHA-1 fingerprint `d01bf1980777823ee7db14f8eac1c353dedb8fb7'
-----BEGIN CERTIFICATE-----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- The hostname in the certificate matches 'phcn.de'.
- Peer's certificate issuer is unknown
- Peer's certificate is NOT trusted
- Version: TLS1.0
- Key Exchange: DHE-RSA
- Cipher: AES-128-CBC
- MAC: SHA1
- Compression: NULL
- Handshake was completed
- Simple Client Mode:
Unfortunately, the above command spits out more than a certificate. Do I need the additional information? If so, what do I need it for? Where do I need to put the certificate file?

Hi,
I recently found out a way how to install test or self-signed certificates and use it with S1SE.
See:
http://www.gtlib.cc.gatech.edu/pub/linux/docs/HOWTO/other-formats/html_single/SSL-Certificates-HOWTO.html
Follow the instructions there
1. Create CA
2. Create root ca certificate
Now install the root-ca-certificate in S1SE -> Security>Certificate Management and Install a "Trusted Certificate Authority".
Paste the contents of the file: cacert.pem into the message-text box.
Then restart the server. Now your CA-Cert should be visible in the Manage Certificates menu.
The next step is to send a certificate-request from S1SE to your e-mail-address.
The contents of the e-mail the server sends to you (certificate request) must be pasted into the file: newreq.pem.
Now just sign the Request:
CA.pl -sign
The last step is that you have to paste the contents of the file newcert.pem into the message-box of the Security>Certificate Management - now under the option Certificate for "This Server".
Then you have to reboot the server/instance again and it should work with your certificate.
Regards,
Dominic

Problem with importing and creating self signed SSL certificate

Mac Pro, 10.7.2 Server. Attempting to import or create a self signed certificate for use as ichat.domain.com to encrypt iChat service. Server is acutally called server.domain.com but has an alias of ichat.domain.com. I understand that this is probably not best practice but I would like to keep things this way since we have one server, run multiple services on it, but want to continue to connect to each service at SERVICE.domain.com. We have been using this type of mismatched certificate with success since 10.4 or so.
I am working through setup of 10.7 Server to replace our 10.6 server.
Tried upgrade of 10.6 to 10.7 installation. The installation made a mess of some services and our Open Directory, but did move the certificate over and allowed iChat service to function properly.
Clean install and setup of 10.7 Server. Exported self signed certificate, private key, and encryption password from 10.6 Server and functioning 10.7 upgraded Server.
On import or manual creation of certificate get the following error:
Error
Check your server's logs for more information. The error (code 5001) was: Expected SecKeychainItemImport to return a SecIdentityRef, but it did not
Log shows:
Dec 29 17:56:55 server servermgrd[498]: -[CertsRequestHandler(HelperAdditions) importP12Data:passphrase:error:]: importedItems = (
"<SecCertificate 0x7fcf6ed43c00 [0x7fff78d96f40]>"
I have tried importing and manually creating other certificates with a variety of names with success. I assume that there is something buried somewhere that is causing this particular one to be a problem. Other than manually removing any remnants of the certificate from /etc/certficates I do not have any ideas what to try. I am essentially ready to move this server to 10.7 except for this problem and would like to avoid a reinstall.
Suggestions?
-Erich

Take a look here.
https://bbs.archlinux.org/viewtopic.php?id=146649
Maybe it's a problem with your network.

Self signed SSL Certificates no longer work after upgrade to 37.0.1

I followed these two articles to create local self signed certificates and they have been working fine since February. Now with the update to 37.0.1 I get "Secure Connection Failed" while trying to access my local website through FireFox. IE and Google Chrome have no problem accessing the local site.
http://www.jayway.com/2014/09/03/creating-self-signed-certificates-with-makecert-exe-for-development/
http://www.jayway.com/2014/10/27/configure-iis-to-use-your-self-signed-certificates-with-your-application/
I have already deleted cert8.db, restarted FF, then re-imported the self signed certificates but get the same error. No other software has changed on this box except the automatic upgrade to FF 37.0.1.
The network setting is already set to use "No Proxy"
How do I fix this?
Windows 8.1 Pro
IIS 8

I have exactly the same problem. All servers and devices that use a self-signed certificate are not reachable anymore via FF37.0.1 after upgrade to FF 37.0.1.
Firefox prints:
"Secure Connection Failed
The connection to the server was reset while the page was loading.
The page you are trying to view cannot be shown because the authenticity of the received data could not be verified.
Please contact the website owners to inform them of this problem."
I'm not getting the chance to add an exception hence no access to the server anymore.
This is a severe problem, because all internally used Glassfish servers in our test environments run with self-signed certificates. As Firefox blocks access to them I cannot maintain my servers anymore.
I have the same problem with Chrome but not with IE - IE is the offers to add an exception but suffers the blank page problem when accessing Glassfish.
I tried to adjust the following values in the FF config:
security.tls.version.min = 0 ;default
deleted cert8.db and restarted FF
I'm really lost, kindly advise.

How to Import Self-signed SSL server certificates in Adobe AIR applications

Hi,
I am using secure AMF endpoints for remote object communication from AIR client.
since i am using a self signed SSL certificate on the server, i am getting a certificate warning message on the AIR client, when ever a remote call is done.
Is there any mechanism to import the server certificate in AIR application..?
Please provide suggestions.
Thanks

I have the same issue along with repeated prompts to accept cert when I am just trying to access the page internally on my network.. Any help here RIM????????

SMTP & Self-Signed SSL

I'm having a strange problem, I can't get SMTP to work using a self-signed SSL certificate. I can get IMAP to work with the cert no problem. And I can submit non-ssl using port 587. But if I try to use SSL, using the self-signed certificate, I get an error in Mail.app saying it can't connect to the server. Any ideas about this?
I did have to edit a few lines in master.cf to make submission on :587 work.

You can see the two lines i uncommented halfway down this thread:
http://discussions.apple.com/thread.jspa?threadID=1433081&tstart=0
SSL is set to USE.
As far as logs go, what do you want to see? SMTP logs after trying to send something via SSL?

Mail for Exchange and SSL certificate

I have a little problem with Mail For Exchange and my Nokia N80. I have self-signed certificate for Exchange mailserver and when I am synchronizing e-mails I got always message: "The site has sent an untrusted certificate. Continue anyway ?". I underestand that my certificate isn't verified by any root authority, but if I have synchronization schedule set at 15 minutes it means I have to confirm this message four times when I am not with my mobile one hour. So question is:
Is possible to import self-signed SSL certificate into Nokia N80 and set it as trusted ? If yes, please describe me how, because I have tried import the certificate as CER (it was opened just as NOTE on Nokia), I tried to convert it via openssl to PEM (the file was not recognized) etc... Thanks for any help in advance.
Reply With Quote

Go to your outlook web access website and click on the lock and then view certificate. The details and then you can save it in DER format to your desktop.
Then go to this site:
http://www.redelijkheid.com/symcaimport/ and insert through the browse button and then copy the link to your phone.
Then you should be able to download it
You can also go to your IIS default site on the exchange server and directory security and export your certificate under edit certificate.
I have tried everything now. I can download my certificate and the valicert from GoDaddy, but the Nokia phone is still saying "do you trust this certificate" every time the phone syncs.
Our firm have taken the E-phones away now and went over to windows mobile and all of them worked within 10 minutes without any errors.
The funny thing is that when you try to call nokia, they wont help you with Mail for Exchange, and it is there program
I know my GoDaddy certificate works on windows mobile phones, so It must be something with Mail for Exchange.
Every guy I talked to about symbian phones have told me they always gives problems with SSL. I am a bit **bleep**, but can conclude that Nokia is for the private consumer.
Best Regards
Morten @ Denmark
Message Edited by asp3200 on 02-May-2008 08:37 AM

Accessing websites running on non-standard ports or with self-signed ssl certs?

I've got some sites running using self-signed ssl's that also run on non-standard ports. Firefox home doesn't seem to open these pages it just sits there with the spinner loading and a blank screen...
Anyone else noticed this?

If the ASA is using a certificate issued by a CA that is in the client's trusted root CA store, then the ASA identity certificate does not need to be imported by the client.
That's why it's generally recommend to go the route of using a well-know public CA as they are alreay included in most modern browsers and thus the client doesn't need to know how to import certificates etc.
If you are using a local CA that is not in the client's trusted root CA store to issue your ASA identity certificate or self-signing certificates on the ASA then you need to take additional steps at the client.
In the first case, you would import the root CA certificate in the trusted root CA store of the client. After that, any certificates it has issued (i.e the ASA's identity certificate) would automatically be trusted by the client.
In the second case, the ASA's identity certificate itself would have be installed on the client since it (the ASA) is essentially acting as it's own root CA. I usually install them in my client's Trusted Root CA store but I guess that's technically not required, as long as the client knows to trust that certificate.

Implementing self-signed SSL on the coldfusion webserver

We've just recently implemented a self-signed SSL on the coldfusion webserver and find that the scheduled tasks are not running.
They don't even appear to "kick off". I'm not receiving an error or notice.
I've attempted pulling-in the cert directly into the Coldfusion JRE folder, and running through the most common answers on the internet regarding use of the cert keytool import - no luck.

I currently have the configureation you are talking about. To allow an iOS device to connect do the following.
1. From the iOS device go to your servers homepage in safari.
2. Login to the profile manager using that individuals userid and password. For some reason I have to login twice the first time I enter the userid and password it will not authenticate the second time it will log the user in.
3. Click the install button next to the "Trust profile" to install it to the iOS device. This will make the iOS device trust the certificate from your personal server.
4. After that you may also install the server profile which will install your vpn and calendar etc... profiles for connecting to the services you have setup on the server onto the iOS device.
5. Once you accomplish this you will be able to access your services via your local lan or vpn.

Create/install self signed ssl cert

I'm evaluating the platform edition server. Is there a quick way to create and install a self signed ssl server certificate (I'm running Windows 2000 pro).
Thanks
Mark

Download the NSS tools from here:
http://wwws.sun.com/software/download/products/3e3afa8e.html
Documentation for NSS tools can be found here (see certutil):
http://www.mozilla.org/projects/security/pki/nss/tools/

Create self signed ssl cert

I'm trying to test the app server. Is there a quick way to install a self signed server certificate (I'm running Windows 2000 pro).
Thanks
Mark

Download the NSS tools from here:
http://wwws.sun.com/software/download/products/3e3afa8e.html
Documentation for NSS tools can be found here (see certutil):
http://www.mozilla.org/projects/security/pki/nss/tools/

Mail.app: Self-Signed SSL Certificates

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