There is a problem with the proxy server's security certificate (internal Outlook 2013 users)

I am receiving the above message for internal Outlook 2013 users when they open Outlook. Despite this message, Outlook is fully functional. External OA users do not see this message. We are using an SRV record for our autodiscover and pointing it to the
name on the single cert we have. I've also already changed the outlookprovider record in Exchange. Any ideas?
TIA!

Hi Alceryes,
According to the error message, Outlook is unable to connect to the proxy server (Error Code 10),
it seems an issue on the Certificate side.
FLAG_CERT_CN_INVALID 0x00000010
More details to see following KB:
http://support.microsoft.com/kb/923575
Would you like to tell me the reason that why you are using SRV record for Autodiscover?
I find a FAQ on Autodisocover for your reference, hope it is helpful:
https://social.technet.microsoft.com/Forums/office/en-US/54bc6b17-9b60-46a4-9dad-584836d15a02/troubleshooting-and-introduction-for-exchange-20072010-autodiscover-details-about-test-email?forum=exchangesvrgeneral
Thanks
If you have feedback for TechNet Subscriber Support, contact
[email protected]
Mavis Huang
TechNet Community Support

Similar Messages

Intermittent proxy error "There is a problem with the proxy server's security certificate. Outlook is unable to connect to the proxy server "

Hi all,
From time to time (at least once a day), the following message pops up on the user's screen:
"There is a problem with the proxy server's security certificate. Outlook is unable to connect to the proxy server . Error Code 80000000)."
If we click "OK" it goes away and everything continues to work although sometimes Outlook disconnects. It is quite annoying...
Any ideas?
Thank you in advance

Hi,
For the security alert issue, I'd like to recommend you check the name in the alert windows, and confirm if the name is in your certificate.
Additionally, to narrow down the cause, when the Outlook client cannot connect again, I recommand you firstly check the connectivity by using Test E-mail AutoConfiguration. For more information, you can refe to the following article:
http://social.technet.microsoft.com/Forums/en-US/54bc6b17-9b60-46a4-9dad-584836d15a02/troubleshooting-and-introduction-for-exchange-20072010-autodiscover-details-about-test-email?forum=exchangesvrgeneral
Thanks,
Angela Shi
TechNet Community Support

There is a problem with the proxy server's security certificate. The name on the security certificate is invalid or does not match the name of the target site "Mailserver"

Good day Guys
First of all I am not an Exchange Expert, and I might be asking a very stupid question, but please bare with me. :)
While I was on leave our Mail server fell over and The company got a Specialist to help out for the time being.
We where\are on Microsoft Exchange 2007 , which Fell over, and the specialist was able to recover as much data as he could.
They then installed Exchange 2013 and tried to migrate everything from 2007 to 2013 and not everything migrated over.
But the problem is, Outlook Anywhere was enable on 2007 and worked a 100% (before the disaster)
With Exchange 2013 I get the following error message when trying to connect With Outlook 2013, using an external connection:
"There is a problem with the proxy server's security certificate. The name on the security certificate is invalid or does not match the name of the target site "Mailserver"
Outlook is unable to connect to the Proxy server. (Error Code 0)"
Has anyone had the Similar when migrating over from 2007 to 2013 or is this an Issue on IIS and nothing to do with Exchange migration?
Your assistance will be greatly appreciated.

Hi,
Firstly, I would suggest we use Exchange 2013 FE as the Outlook Anywhere proxy server.
For the certificate issue, it mostly occurs because the host name that Outlook are trying to access does not match the certificate SAN. Please check with this point. If they do not match, you
can change the host name by referring to the following article:
https://support.microsoft.com/kb/940726/en-us?wa=wsignin1.0
Thanks,
Simon Wu
TechNet Community Support

Outlook 2013: There is a problem with the proxy server's certificate

Hello!
One more question regarding Outlook 2013/Exchange2013SP1:
There are three lab PCs: DC, Exch1, Exchange2. There's a wildcard certificate installed on Exch1 (https://social.technet.microsoft.com/Forums/en-US/6a440c99-47bd-4f48-8cc5-9f92e6b06496/wildcard-certificate-for-exchange-2013?forum=exchangesvrgeneral).
OWA works perfect with this wildcard certificate.
I install Outlook2013 on Exch1 and get the error:
DC.Entreprise.Local is a computer certificate issued for the computer DC.Enterprise.Local.
DC.Enterprise.Local IS NOT (and never was) the proxy for Exch1 or Exchange2:
How Outlook could request DC's certificate if the proxy server = Exch1.Enterprise.Local???
Thank you in advance,
Michael

Hello all,
Thank you for your replies!
Since I'm using a wildcard certificate I changed Outlook providers according to this:
http://blogs.technet.com/b/exchange/archive/2013/08/02/part-2-reverse-proxy-for-exchange-server-2013-using-iis-arr.aspx
If you do choose to use a wildcard certificate, you should also make sure that you
change the EXPR Outlook Provider, so that Outlook Anywhere clients can successfully connect to the Exchange Server (this behavior can be a particular issue
if you have Windows XP clients). If you do not make this change then end users may continue to receive a prompt for a certificate mismatch."
...and EXCH and EXPR are both set to *.Enterprise.Local.
"I install Outlook2013 on Exch1" you mean you install Outlook on top of Exchange?" - on the same server as Exchange, and in this case Outlook must use SCP, not DNS (the server and the client are in the same AD domain).
"Without SCP, Exchange try DNS autodiscover lookup, first site it will try is
https://emaldomain/autodiscover/autodiscover.xml, which happen to be resolve to your domain controller." - I think that's the case... I just don't understand why
an internal client can't find the SCP that does exist and point to exch1.enterprise.local:
Regards,
Michael

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There is a problem with the security certificate of the proxy server. Error code 18 and 38.

Hi All,
After several hours and a short night of sleep I'm out of ideas and hopefully someone here can help me trying to solve this one. First of all the situation:
Exchange 2013 on a remote location with a CA-certificate.
Outlook 2010 and 2013 on different locations, locally installed and on RDS.
When I open Outlook on my laptop all is fine, no errors, good sync, no problem. But when I open Outlook on our Remote Desktop Servers with Outlook 2013 I'm getting errors like "There is a problem with the security certificate of the proxy server. The
name on the security certificate is invalid or does not match the name of the site. Outlook is unable to connect to this server. (Error code 18)". Opening Outlook 2010 the message is the same, but the error code now is 38.
After this Outlook opens and is working, there's one more error though. After a while an security warning pops up with the message: "Information you exchange with this site cannot be viewed or changed by others. However, there is a problem with the
site's security certificate. * The security certificate was issued by a company you have not chosen to trust. View the certificate to determine whether you want to trust the certifying authority. * The security certificate is valid. * The name on the security
certificate is invalid or does not match the name of the site."
Strangest thing is, it is the certificate of my RDS! It isn't my valid en officially bought certificate from my mailserver. What's going on? I'm out of options, what I've tried so far (in random order):
- restarting mailserver and AD;
- restarting switches;
- restarting routers;
- restarting RDS, AD and all other servers;
- bypassed proxyserver for RDS;
- created a new profile;
- checked recently installed updates;
- checked certificate on mailserver;
- checked RDS on a different location, working fine.
Nothing helped, what can I do next? Please advice.
Regards.

Found a thread that solves half my problem (https://social.technet.microsoft.com/Forums/office/en-US/70d18244-889a-4d95-ac3f-e234672a82b2/there-is-a-problem-with-the-proxy-servers-security-certificate-error-when-starting-outlook?forum=exchangesvrclients).
The first message can be suppressed by adding this to the Exchange config:
set-outlookprovider -Identity EXCH -CertprincipalName msstd:webmail.domain.tld
set-outlookprovider -Identity EXPR -CertprincipalName msstd:webmail.domain.tld
Giving the command get-outlookprovider, gives me empty information regarding the certprinipalname. Filled
this and after recreating the profile or deleting the ost-file I still have the second alert with the local certificate of my RDS.
Not completely where I want to be, any help regarding the second alert is greatly appreciated!

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502 - Web server received an invalid response while acting as a gateway or proxy server.
There is a problem with the page you are looking for, and it cannot be displayed. When the Web server (while acting as a gateway or proxy) contacted the upstream content server, it received an invalid response from the content server.
Regards, Ganesh, MCTS, MCP, ITILV2 This posting is provided with no warranties and confers no rights. Please remember to click Mark as Answer and Vote as Helpful on posts that help you. This can be beneficial to other community members reading the thread.

When i try with https://lyncfrontend.domain.local:4443 and https://lyncfrontend.domain.com:4443 both opens but when i open the external domain name i get certificate .
ARR version installed is 3.0
To throw more light on the configuration:
Lync 2013 implemented, internal domain name is : domain.local and external domain name is : domain.com
All servers in VMs are with 4 core processor, 24gb ram, 1TB drive.
Frontend : Windows 2012r2 with Lync 2012 Standard Edition - 1 No (192.168.10.100)
Edge : Windows 2012 with Lync 2012 Std - 1 No
(192.168.11.101 DMZ) in workgroup
ISS ARR Reverse Proxy 3.0 : Windows 2012 with ARR and IIS configured. (192.168.11.102)
Certificate : Internal Domain root CA for internal and External (Digicert).
Internal Network : 192.168.10.x /24
External Network (DMZ) : 192.168.11.x /24
Public Firewall NAT to DMZ ip for firewall and RP server. So having two public IP facing external network.
Edge has : sip.domain.com, webconf.domain.com, av.domain.com
IIS ARR RP server has : lyncdiscover.domain.com, lyncweb.domain.com, meet.domain.com, dialin.domain.com
Have created SRV record in public : _sip.tls.domain.com >5061>sip.domain.com, _sipfederationtls._tcp.domain.com>5061>sip.domain.com, _xmpp-server._tcp.domain.com>5269>sip.domain.com
Installed frontend server using MS Lync server 2013 step by step for anyone by Matt Landis, Lync MVP.
Internal AD Integrated DNS pointing Front-end
Type of Record FQDN
IP Description
A sip.domain.com
192.168.10.100 Address internal Front End or Director for internal network clients
A admin.domain.com
192.168.10.100 URL Administration pool
A DialIn.domain.com
192.168.10.100 URL Access to Dial In
A meet.domain.com
192.168.10.100 URL of Web services meeting
A lyncdiscoverinternal.domain.com
192.168.10.100 Register for Lync AutoDiscover service to internal users
A lyncdiscover.domain.com
192.168.10.100 Register for Lync AutoDiscover service to external users
SRV Service: _sipinternaltls Protocol: _tcp Port: 5061
sip.domain.com Record pointer services to internal customer connections using TLS
External DNS pointing Edge & Proxy
Type of Record FQDN
IP Endpoint
A sip.domain.com
x.x.x.100 Edge
A webconf.domain.com
x.x.x.100 Edge
A av.domain.com
x.x.x.100 Edge
SRV _sip._tls.domain.com
sip.domain.com: 443 Edge
SRV _sipfederationtls._tcp.domain.com
sip.domain.com:5061 Edge
A Meet.domain.com
x.x.x.110 Reverse Proxy
A Dialin.domain.com
x.x.x.110 Reverse Proxy
A lyncdiscover.domain.com
x.x.x.110 Reverse Proxy
A lyncweb.domain.com
x.x.x.110 Reverse Proxy
In IIS ARR proxy server following server farms are added and configured as per link ttp://y0av.me/2013/07/22/lync2013_iisarr/
In proxy server had setup only following server farm : While running remote connectivity web service test : meet, dialin, lyncdiscover and lyncweb.
The client inside works fine internally and through vpn. Login with external client also working fine. But we are getting error in MRCA as follows.
a) While testing remote connectivity for lync getting error : The certificate couldn't be validated because SSL negotiation wasn't successful. This could have occurred as a result of a network error or because of a problem with the certificate installation.
Certificate was installed properly.
b) For remote web test under Lync throws error : A Web exception occurred because an HTTP 502 - BadGateway response was received from IIS7.
HTTP Response Headers:
Content-Length: 1477
Content-Type: text/html
Date: Wed, 14 May 2014 10:03:40 GMT
Server: Microsoft-IIS/8.0
Elapsed Time: 1300 ms.
Regards, Ganesh, MCTS, MCP, ITILV2 This posting is provided with no warranties and confers no rights. Please remember to click Mark as Answer and Vote as Helpful on posts that help you. This can be beneficial to other community members reading the thread.

HT4864 I am getting a triangle with an exclamation point next to my inbox...it says: There may be a problem with the mail server or network. Verify the settings for account "MobileMe" or try again. The server returned the error: Mail was unable to log in

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This is the messege I am gewtting:
There may be a problem with the mail server or network. Verify the settings for account “MobileMe” or try again.
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Why do I get an "unable to connect - There may be a problem with the mail server or network." message from iCloud. I have verified the settings. I can access my iCloud account online but can't send or receive e-mail via the mail account.

Text limits to the "Question" link prevents a full explanation:
This is a long-time problem. I have tried to resolve it with Apple but their "Customer Support" is merely a name.
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"The server returned the error: The server 'p0-imap.mail.me.com' refused to allow a connection on port 143."
Well, I have verified the setting and tried again and again and …
Well, you get the idea …

JungleTaxi Cabbie wrote:
Csound1: iCloud: Configuring Mail with Mac OS X v10.6 or iOS 4
Enter your Incoming Mail Server, User Name, and Password using the following settings:
Incoming Mail Server: mail.me.com
User Name: Your iCloud email address (excluding @me.com)
Password: Your password
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Maybe you should test these things before calling people out, because these settings do function perfectly well.
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The OP has an iCloud account, and that can not be opened without Lion or Mountain Lion (on a Mac), IOS5 or 6 (on an iPhone/iPad)
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Also, if you're not running Lion or Mountain Lion, there is no "Mail, Contacts & Calendars" prefpane.
I never said that there was, perhaps you imagined it.

There is a problem with the server's security certificate. The security certificate is not from a trusted certifying authority. SAP Business One is unable to connect to the server

Hello,
I have an issue with connecting client SB1H on Windows, the scenario is as follows:
1.- Server:
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     NDB and Server are review 69 SP06
2.- Client:
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     SAP HANA Studio version 1.0.60
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Hi,
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SCOM - -500 Internal Server Error - There is a problem with the resource you are looking for, and it cannot be displayed

Hi There,
Need your assistance on the issue that we are facing in prod environment.
We are able to open web console from remote machine and able to view monitoring pane as well as my workplace folders from console . Able to view and access alerts and other folder in the monitoring pane. We are able to view and access My Workplace folder
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http://social.technet.microsoft.com/Forums/en-US/7675113e-49f0-4b3a-932b-4aceb3cfa981/scom-500-internal-server-error-there-is-a-problem-with-the-resource-you-are-looking-for-and-it?forum=operationsmanagerreporting
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I still have problems with getting my website online. I have defined my server. Then I did the test and there was a connection via FTP. I put my files on the external server and there is a connection with the external server. But when I check to see my we

I still have problems with getting my website online. I have defined my server. Then I did the test and there was a connection via FTP. I put my files on the external server and there is a connection with the external server. But when I check to see my website online (with Firefox, Explorer, Chrome browser) I always get the message 'Forbidden, You don't have permission to access / on this server.' Can somebody help me please? I have to get my website online..Thank you!

Hello Els,
it's well known, that in all these cases you describe I'm not a friend of a detailed Troubleshooting (I see Nancy#s smile already).
To be able to be independent in all this things It is one of the reasons why I prefer an external FTP program. The difficulties with which you have to fight encourage me in this opinion, not least because we always search for experts, we don't charge a "jack of all trades".
To manage several websites or to upload my files and sometimes for the opposite way, for a necessary download from my server or to use a "a site-wide synch", I'm using FileZilla. It simply looks easier for me to keep track of all operations precisely and generate or reflect easily the desired tree structure.
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And even if it means you have to install a new program, I am convinced that there is an advantage. Here is the link to get it and where you can read informations about how it works:
http://filezilla-project.org/ and http://wiki.filezilla-project.org/Tutorial#Using_the_site_manager
Mac: Mac OS X (Use: Show additional download options)
http://filezilla-project.org/download.php
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Hans-Günter
P.S.
Since I use two screens, the whole thing became even more comfortable.

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There is a problem with the proxy server's security certificate (internal Outlook 2013 users)

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