Entourage 2008 + Exchange + Certificates

This is regarding the compatibility with Exchange 2008, Entourage 2004/2008, and mainly the proper way to get a security certificate installed. I have done some research and found that you know that your cert is installed correctly if when you visit the HTTPS:// address you no longer get a UNAUTHORIZED warning. So that means I have installed the cert properly but I am still getting this error.
Entourage is unable to access the mail account you are using with the mail server configured for this account (It is telling me to check my account settings, but I know they are all correct, the only thing that changed was the DNS name of my exchange server)
I have also read around that Entourage 2004 is no longer supported, but 2008 is. Also that they are recommending the use of Apples Mail application appose to Entourage, because Apple has taken allot of time setting up back end Exchange side with the Mail application. I am hoping to not have to switch my entire production team to Mail. It would mean they lose all their local messages that they have received over the year. Any help would be awesome.

Since this question is about a Microsoft product, you might have more luck getting suggestions if you ask in Microsoft's own forums.
Good luck.

Similar Messages

Entourage 2008 Exchange to Outlook Web Access

Okay, bear with me: I'm an end-user and not especially technically inclined.
That said, for years I've used Entourage 2008 as my email client (on a MacBook Pro, OSX 10.9), and it successfully works with the web-based Outlook account that my ISP provides, through a POP connection.
Now, I'd like to sync my Entourage calendar with one in Outlook.
Importing the Entourage calendar into Outlook was easy. But when I build an Exchange account in Entourage, I seem to have fallen on my face.
It still imports mail, but can't send mail
It doesn't sync the Outlook calendar (on the web) to Entourage's
I have upgraded Entourage to the EWS version of 12.3.6.
After configuring the Web Services Edition (as best I could), I still can't send email — or sync Entourage to the online Outlook calendar.
Here's the error message: "Unexpected data was encountered" Error: -17997
I'm using the same settings I see in my Nokia N8 mobile's Exchange mailbox settings (which works perfectly with Outlook including syncing its calendar with OWA's calendar).
What puzzles me is that an Exchange account on Entourage and my MacBook won't work using the same settings as Exchange ActiveSync on my Nokia N8, which syncs flawlessly with OWA. Any and all suggestions gratefully received.

An additional point of information. You've posted to an Exchange 2013 forum. Is your Exchange organization running Exchange 2013? If not, the Exchange previous versions forums are here:
http://social.technet.microsoft.com/Forums/en-US/category/exchangeserverlegacy.
You should share the Exchange version, service pack and update level you're running.
If you believe that it's an Exchange configuration problem as opposed to Entourage, then the issue would likely be in the configuration of Exchange Web Services, particularly the EWS virtual directory.
Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

Entourage 2008 does not have certificate???

Hello
I've tried setting a pop account on entourage 2008 for mac.
Error: Unable to establish a secure connection to xxxxxxxxx because the correct root certificate is not installed.
I go to Entourage Tools - Account - Mail Security - Signing Certificate - Select=
Entourage did not find any valid certificates on the Mac OS keychain.
How can I solve this problem?
Thank you

Hi,
1st, Open Keychain Access in Utilities, use Keychain First Aid under the Window Menu item.
Resetting your keychain in Mac OS X...
If Keychain First Aid finds an issue that it cannot repair, or if you do not know your keychain password, you may need to reset your keychain.
http://support.apple.com/kb/TS1544
Then ssee this...
http://www.entourage.mvps.org/smime/index.html

Entourage 2008 EWS Attachment limit on Exchange 2010

Hi Folks,
I'm having a problem allowing my Entourage users to attach files larger than 10MB. I've looked through all of the potential attachment limits on Transport config/Send connectors/Receive connectors/Users mailbox settings, but they all look okay to me.
[PS] C:\Windows\system32>get-mailbox user | fl max*
MaxSafeSenders    :
MaxBlockedSenders :
MaxSendSize       : 150 MB (157,286,400 bytes)
MaxReceiveSize    : 150 MB (157,286,400 bytes)
[PS] C:\Windows\system32>get-sendconnector | fl max*
MaxMessageSize : 150 MB (157,286,400 bytes)
MaxMessageSize : 150 MB (157,286,400 bytes)
[PS] C:\Windows\system32>get-receiveconnector | fl max*
MaxInboundConnection                    : 5000
MaxInboundConnectionPerSource           : unlimited
MaxInboundConnectionPercentagePerSource : 100
MaxHeaderSize                           : 64 KB (65,536 bytes)
MaxHopCount                             : 30
MaxLocalHopCount                        : 8
MaxLogonFailures                        : 3
MaxMessageSize                          : 150 MB (157,286,400 bytes)
MaxProtocolErrors                       : 5
MaxRecipientsPerMessage                 : 5000
MaxAcknowledgementDelay                 : 00:00:30
MaxInboundConnection                    : 5000
MaxInboundConnectionPerSource           : 20
MaxInboundConnectionPercentagePerSource : 2
MaxHeaderSize                           : 64 KB (65,536 bytes)
MaxHopCount                             : 30
MaxLocalHopCount                        : 8
MaxLogonFailures                        : 3
MaxMessageSize                          : 150 MB (157,286,400 bytes)
MaxProtocolErrors                       : 5
MaxRecipientsPerMessage                 : 200
MaxAcknowledgementDelay                 : 00:00:30
[PS] C:\Windows\system32>get-transportconfig | fl max*
MaxDumpsterSizePerDatabase : 100 MB (104,857,600 bytes)
MaxDumpsterTime            : 7.00:00:00
MaxReceiveSize             : 150 MB (157,286,400 bytes)
MaxRecipientEnvelopeLimit : unlimited
MaxSendSize                : 150 MB (157,286,400 bytes)
I'm running Exchange 2010 (with Rollup3 installed), on Server 2008R2.
My clients are running Entourage 2008 EWS, patched up with the latest Office Mac updates.
Apart from their inability to send 10+MB attachments, everything else is fine.
Regards,

Shane
Toutges solution worked for us. Exchange Server 2010 (current patch level as of March 2015), Mac OS Outlook 2011 via EWS.
Key to the solution is this revision:
maxReceivedMessageSize value
to [example value]
51200000 underneath the heading <EWSMessageEncoderSoap11Element />. There are 6 places to make this change (bytes)
I have not seen this noted under the several MS Tech Net articles that pertain to the problem of sending large email attachments via Mac Outlook 2011 via EWS.

Snow Leopard-Exchange Server 2003-Entourage 2008 (12.2.1)

+I have one final question before I upgrade to Snow Leopard.+
I currently run a 2.8 GHz Mac Pro, Leopard 10.5.8, Entourage 2008 (12.2.1) using Exchange server 2003. Everything is happy and works well.
I understand that I won't be able to use the new Snow Leopard built-in Exchange Server support.
*But, if I upgrade to Snow Leopard...will everything stay happy with what I've been running?*

There are connectivity issues between Exchange Server 2003 and Exchange accounts in Entourage 2008 running on Snow Leopard. These connectivity issues are also evident via web-based email (Safari & FireFox) on Snow Leopard and Exchange Serve 2003.
You will eventually loose connection to Exchange Server 2003. Restarting your computer will solve the problem temporarily.
POP accounts appear to work fine in this environment.

How can I share a project specific calendar I created on Entourage 2008 ?

How can I share a project specific calendar I created on Entourage 2008 without showing my personal calendar? I created a project specific calendar using Entourage 2008 for Mac. I want to add someone that uses Outlook from a PC. We are in the same exchange network. I have added this person in under the sharing tab, but don't see a way to invite her to view it, and it does not appear on her Outlook list of shared calendars. I was able to invite her to view my main calendar, but not the project specific one. Any suggestions?

http://www.microsoft.com/mac/support

Checklist for Exchange Certificate issues

Checklist for Exchange Certificate issues
1.
Why certificate is important for Exchange and What are Certificates used for
Exchange is now using certificates for more than just web, POP3, or IMAP. In addition to
securing web services, it has also incorporated Transport Layer Security (TLS) for session based authentication and encryption.
Certificates are used for several things on Exchange Server. Most customers also use certificates
on more than one Exchange server. In general, the fewer certificates you have, the easier certificate management becomes.
IIS (OWA, ECP, EWS, EAS, OA, Autodiscover, OAB, UM)
POP/IMAP
SMTP
2.
Common symptoms for
certificate issue
Here we can see three different types of the certificate warning, mainly from the Outlook
side.
a.
Certificate mismatch issue
b.
Certificate trust issue
c.
Certificate expiration issue
3.
Checklists
In this section, checklists will be provided according to the three different scenarios:
Certificate Mismatch Issue
[Analysis]:
This issue mainly occurs because the URL of the web services Outlook tries
to connect does not match the host name in the certificate.
[Checklist]:
Firstly make sure how many host name in your certificate the certificate. Run “Get-ExchangeCertificate | select certificatedomain”.
Secondly, check the web services URLs which Outlook are trying to connect to. Run “Test Email AutoConfiguration”
In this scenario, you need to check the host name for the following services:
Autodiscover
EWS
OAB
ECP
UM
If any of the urls above does not match the one in the certificate, refer to the following article to change
it via EMS:
http://support.microsoft.com/kb/940726
1.
Do not forget to restart the IIS service after applying the changes above.
2. Make sure a valid certificate is enabled on the IIS service.
Certificate Trust Issue
[Analysis]:
For the self-signed and PKI-based (Enterprise)
certificates, they are not automatically trusted by the client computer or mobile device, you must make sure that you import the certificate into the trusted root certificate store on client computers and devices. On the other hand, Third-party or commercial
certificates do not have this problem. Most commercial CA certificates are already trusted because the certificate already resides in the trusted root certificate store. Because the issuer is trusted, the certificate is also trusted. Using third-party certificates
greatly simplifies deployment.
[Checklist]:
If it’s an Enterprise CA certificate, manually install the root certificate to the “Trusted Root Certification Authorities” folder:
If it is a 3<sup>rd</sup>-party certificate, first remove and reinstall the certificate. Check whether the Windows Certificate Store on the local
client is corrupted. If it still does not work, please contact the third-party CA support to verify the certificate.
Certificate Expiration Issue
[Checklist]:
When a certificate is about to expired, we just need to renew it by referring the following article:
Renew an Exchange Certificate
http://technet.microsoft.com/en-us/library/ee332322(v=exchg.141).aspx
To avoid any conflictions, it’s recommended to remove the expired certificate from the certificate store.
[How to set a reminder to alert the administrator when a certificate is about to expired]:
It’s easy to fix the certificate expire issue. But it should be more important to set a reminder before the
certificate expiration. Or there can be a large user impacts.
Generally, the Event ID “^(24|25)$” will appear in Application log when a certificate is about to expire.
If it’s not quite visible, we can refer to the following solution:
http://blogs.technet.com/b/nexthop/archive/2011/11/18/certificate-expiration-alerting.aspx
OWA certificate revoked issue
[Analysis]:
IE
includes support for server certificate revocation which verifies that an issuing
CA has not revoked a server certificate. This feature checks for CryptoAPI revocation when certificate extensions
are present. If the URL for the revocation information is unresponsive, IE cancels the connection.
[Solution or workaround]:
1. Contact CA provider and check whether the questioned certificate is in the Revoked List.
2. If not, check whether the certificate has a private key.
3. Remove the old certificate and import the new one.
Workaround:
IE Internet Options -> Advanced tab -> Clear the "Check for server certificate revocation"
checkbox.
4.
More References
Digital Certificates and SSL
http://technet.microsoft.com/en-us/library/dd351044(v=exchg.150).aspx
More on Exchange 2007 and certificates - with real world scenario
http://blogs.technet.com/b/exchange/archive/2007/07/02/3403301.aspx

(Reported previous post with link to SIS package to moderator)
This is not the correct SIS package for the N73. The package shown is for S60 3.2 devices, but the N73 is not S60 3.2, I believe it is S60 3.0.
Most features may work with this SIS, but if you experience strange problems, try using the S60 3.0 version.
But there are no significant difference between 2.5.3 and 2.5.5 with regard to attachments. The only changes were with localization (languages).
At this point, try 2.7.0 which is out now:
http://businesssoftware.nokia.com/mail_for_exchange_downloads.php
Make sure to pick the right phone on the drop down list. It does matter! There are 4 different packages. This list makes sure you get the right one.
I have seen some issues with attachments not completing that seem to be carrier dependent. You can test this my using Wifi (if possible).
Message Edited by m4e_team_k on 28-Sep-2008 12:25 AM

Entourage 2008 - Importing from Outlook 2007 ???

Hi guys, just got a MacBook Pro this week and I had reserved a copy of Office 2008 which I got today.
It's great because that's what I was waiting for to put my PC on sale
BUT i was astonished to see that there's not the option to import pst files in Entourage ??
I was using Office 2007 for PC therefore Outlook 2007.
The only way we can export stuff is by creating .PST files, so you can backup all your contacts, your messages with attachements and your calendar (which are my 3 priorities).
Using the equivalent application from Microsoft but for the Mac, that is : Entourage 2008, there's not the option to import .pst ?? What the heck ??
So please guys if you know a way to export my stuff (messages, contacts and calendar) from Outlook 2007 PC to Entourage 2008 MAC, please let me know !!!
THANK YOU !!

Hey guys,
I don't want to be repeting by here's the way I worked this out :
EMAILS
First I installed Thunderbird on my Win computer.
Then I imported from outlook. It took a while since my PST was like 3 Gb.
At first I was crashing it but then I let it work for a try and it imported everything perfectly, but not showing any progress bar during the process.
Second, I searched Thunderbird help for the way to export in MBOX, and it pointed out that I sould get a plug-in, which I did.
Third, having installed the plug-in, I had a tool menu for exporting. Only thing I had to do is select each folder one by one and export them using this plug-in, I only had to add .MBOX extention to every file.
Finally, when you get these files in OS X with entourage, you just drag and drop them in entourage and them import perfectly.
That did the job for me anyways.
CONTACTS
Send yourself emails of contacts !
I sent myself email (with the WORK OFFLINE option so I wouldn't receive them in outlook) in the contacts from outlook.
As you can imagine, I totally got rid of Outlook, and of Windows actually, by now but as I remember it when you right click on a contact you have an item that's called something like "send full information of contact through email".
So to keep my categories I sent one email per categories.
Back in entourage, I had to save attachements, import them, put them in a category.
Then next email, etc. and so on.
CALENDAR
I haven't found a way to do this but what I did was : In outlook you have a way to display your calendar events by a list, so I just made a couple of print screen of that list and I put the future events that I wanted to keep in Entourage.
And the conclusion is :
Well I said byebye to Entourage because I don't need MS Exchange support and I hate Microsoft more and more everyday so I'm using Mail, Address Book and iCal now
But I could easily import from entourage into all of these.
The only microsoft apps I still are the must-have : word, excel and powerpoint 2008.

Entourage 2008 & iCal sync inaccurate free / busy status for events

On a campus using Exchange 2007, I am using Entourage 2008 and sync to iCal 3.0.2 (Leopard) via Sync Services in Entourage's preferences. Both Exchange 2007 and Entourage 2008 have only been installed in the last two months.
I have found that events which I mark as "free" in Entourage 2008 are changed to "busy" after a sync with iCal. The free / busy status is correct when the sync with Exchange takes place, but the status is incorrectly changed to busy every time the iCal sync takes place.
I need to put campus events, co-worker planned absences, and similar things on my calendar, but these items need to remain as "free" so that I can be scheduled during those times. This all worked correctly with Entourage 2004 and the older version of Exchange.
Does anyone know how to correct this behavior so that the free / busy status is not changed with a sync to iCal?

Sue,
Wish I could offer some good advice, but the easy syncing of iCal and Entourage 2008 so far has been impossible if not a nightmare.
When you go to import in Entourage and iCal is NOT listed as "another application", we are in HUGE trouble.
A real shame that in today's world of "New Media" and PDA's like iPhones and Blackberry that the two billionaires from Apple and MS did not provide us with easy and simple export/import/sync tools.
Maybe they should rename Office 2008 to Office 1984

RESOLVED On Premises (intranet use only) Exchange Certificate Help (Please)!

I apologize in advance for what may end up being a very silly issue.
I have racked my brain and read and searched and I still can't seem to find the answer to my question.
I have an in house Exchange server that is only accessible internally. We do not have external clients (laptops/tablets/etc) and all computers stay on premises. Most of our clients use OWA to access email. Everything has been working fine up until about
2 weeks ago when everybody started getting a certificate error. I have tried every thing I can find to fix this issue to no avail. It seems the thumbprint of the certificate is different each time I visit the exchange server (https://exchange/owa). So I can
install the certificate which works for a few minutes and then it prompts me again. When looking at the thumb print of each instance, everything seems to be exactly the same with the exception of the thumbprint.
My first question, is do I still need to go through a CA even though this server is not accessible via external IP?
Where are my clients getting the certificate they are trying to install because they do not match the certificate that is installed on the Exchange Server.
Thank you in advance for anybody that can steer me in the right direction to getting this resolved.
I support this site remotely so any additional info can be provided but there might be a small delay.

First, thank you for taking the time to respond.
"I'm going to assume that you have some sort of PKI infrastructure with in your environment."
I'm not sure I do. This project landed in my lap a few years ago. This particular client is my only client
with exchange. I have limped my way though to this point but I'm afraid I'm just not clear on what it is I actually need.
We are running Exchange 2013 on a Server 2008 box. Everything worked fine up until about 2 weeks ago. I have no idea what changed.
I think my biggest problem is my lack of understanding of where the client is pulling the certificate when I access the intranet site. I don't understand why the certificate (whether valid or not) isn't matching the certificate within IIS/Exchange admin.
Hi,
I think you can check your certificate information and provide the information here for more help. Please run the following command in Exchange Management Shell:
Get-ExchangeCertificate | fl
Additionally, since the certificate issue occurs when accessing Exchange server from OWA, please check the OWA configuration in your Exchange:
Get-OwaVirtualDirectory | FL Identity,*Authentication*,*url*
Generally, the namespace used in the OWA URL should be included in the Exchange certificate which is assigned with IIS service.
Regards,
Please remember to mark the replies as answers if they help, and unmark the answers if they provide no help. If you have feedback for TechNet Support, contact [email protected]
Winnie Liang
TechNet Community Support

Saving archived emails for entourage 2008 on 2 different MacBooks

I use a Entourage 2008 on Macbook Pro at work on an exchange server and archive emails to specific files on my computer section. This allows me to keep the record of the email and keep the mailbox size appropriate for work. At home I have a separate Macpro with Entourage and want to "see" the archived emails.It is difficult to "synch" them if I saved at different locations.
Previously in outlook, I could do this by saving the PST file on the shared folder and pointing to that file when I opened the outlook at home. The file would be always current. IS there a way to do this in Entourage? Is there a specific way to point to the database, so that either work or home opens to a "shared" drive rather then the local C drive?

I use a Entourage 2008 on Macbook Pro at work on an exchange server and archive emails to specific files on my computer section. This allows me to keep the record of the email and keep the mailbox size appropriate for work. At home I have a separate Macpro with Entourage and want to "see" the archived emails.It is difficult to "synch" them if I saved at different locations.
Previously in outlook, I could do this by saving the PST file on the shared folder and pointing to that file when I opened the outlook at home. The file would be always current. IS there a way to do this in Entourage? Is there a specific way to point to the database, so that either work or home opens to a "shared" drive rather then the local C drive?

Entourage 2008 calendar sync with Outlook 2007

For all you Entourage 2008 & Outlook users out there, is it possible to schedule calendar appointments in Outlook and have them appear in Entourage?
The opposite of that, scheduling appointments in Entourage and viewing in Outlook, works w/out issue but still scratching my head on why the reverse doesn't.
(btw, backend is Exchange 2007)

*"is it possible to schedule calendar appointments in Outlook and have them appear in Entourage?"*
Yes.
Since neither are Apple products, you should consider posting your question on Microsoft's own forums for their Mac products, as they would be geared more toward any issue you have then a forum focusing on Apple's own Mail applications:
http://www.officeformac.com/productforums

Entourage 2008 full day events displayed on the wrong day

Hi
I am using Entourage 2008 with an exchange server and a blackberry. As well I have a Windows notebook with MS Outlook.
My problem is: If I setup a full day event it will be displayed correct on my outlook and my blackberry BUT entourage will show this event on the wrong day (24 hours to early!?!)
Does anybody know what I am doing wrong?
My timezone is set correct (in Entourage and on my iMac)?!?!
Thanks for help....

I think I received a reply
Please check
This is an Exchange issue. See this article for details. It also applies to
Exchange 2007 although the article talks about 2003.
http://support.microsoft.com/kb/925376
Thanks
Mu
Thanks to Mu for the help. I will get in contact with my provider if there is a chance to install the hotfix.

Entourage 2008 won't sync to iCal since 10.5.3

Hi,
Since I updated to 10.5.3, Entourage 2008 won't sync to iCal. I've already tried to uncheck the sync option in Entourage preferences and check it again using the "Entourage replaces iCal" option. Contacts seem to sync to address book normally. However, my Exchange calendar in Entourage won't replace iCal items. Both iCal and Exchange calendar in Entourage seem to have merged (which is a big problem for me). After this unfortunate merge, nothing is syncing in one direction or another...
Any help appreciated!

Maybe this could be a better solution. Since the problem is only with Entourage, I did some diggin' and found out that there seems to be a problem with Entourage SyncService-Registration.
The easiest solution is:
1) Switch off syncing in Entourage and quit Entourage, iCal, AddressBook, Mail
2) Kill SyncServer (via ActivityMonitor)
3) Delete contents of Library/Application Support/SyncServices/Local/
4) Start iCal, AddressBook, Mail, Entourage
5) Switch on syncing in Entourage
Best
imdat

Installer could not locate the data it needed... Entourage 2008

Hi, I'm a bit of newbie to Mac's... I am trying to work out why a copy of Entourage 2008 I have wont install... I have posted on the Mactopia forums but with no success, so I thought I would try here, as I am not sure if it is an Entourage/Microsoft issue or a Mac OS issue. Every time I try to install my downloaded e2008.iso (came with my Exchange server rental) I get the following error: "Install Failed. The installer could not locate the data it needed to install the software. Check your install media or internet connection and try again or contact the software manufacturer for assistance". I am assured that the download I have is complete and 'verified'. When I double click the .iso file, it mounts and then opens - i then click through 'Office Installer_mpkg / contents / distribution.dist to begin the install. If anyone has any advice on what I might be doing wrong I would appreciate it! Thanks.

Thanks - it is reputable (should be...) as it is from the company i get my exchange server rental through, part of the 'package' is a download of entourage or outlook. Unfortunately they do not offer very good mac support... Have gone back to them to make it their problem! thanks all the same.

Entourage 2008 + Exchange + Certificates

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