Exchange 2010/Outlook 2011 woes

A cautionary tale for anyone thinking of upgrading to an Exchange 2010 server. I have been working successfully with Mail/iCal/Address Book on an Exchange 2007 for over a year. My hosted exchange provider offered a free upgrade to Exchange 2010, and I decided to purchase Office 2011 to use Outlook. Big mistake. Now I am stuck with the following issues:
1. Mail has an incompatibility with Exchange 2010 - sent messages lack a "From:" field in the raw message source (see http://discussions.apple.com/message.jspa?messageID=12591913)
2. My hosted Exchange provider also has a Blackberry Enterprise server. But when you file sent messages in Outlook 2011, they fail to appear in the corresponding Blackberry subfolders - they disappear from the main message list and then do not appear in the subfolder. Received messages file with no problems - sent ones don't. Very weird, and very annoying. Sent messages filed in subfolders via Outlook Web Access appear properly on the BB handheld.
3. Time zones in Outlook 2011 conflict with the Exchange server. Adding an appointment via the Blackberry, the appointment initially appears in the correct place, then a few seconds later, jumps an hour forward. Quitting Outlook on the desktop machine solves the problem... Outlook has Sydney as GMT+11, which is incorrect. It is GMT+10, but with an extra hour for daylight saving in summer. The server settings, as displayed on Outlook Web Access, correctly show Sydney as GMT+10.
As a result, I am now stuck using Outlook web access as my only reliable mail/calendar application, with all the limitations that that entails (no recall of previously used email addresses for example). And I will now have to wait for either a new version of Outlook, or a new version of Mail...
Any other users experiencing any of these issues?
Thanks in advance.

I'm in the middle of a PC -> Mac migration and have hit a lot of snags with Exchange 2010.
All clients are running 10.6.4. Mail and Contacts seem to be working properly. iCal however is very problematic. When attempting to add shared calendars through the delegation tabs of Account Settings I am able to find the accounts, add them to the delegate list, but the client is not able to grab any calendar data.
I've got another issue which is Outlook 2011 font sizes being way to small for my older users, and the inability to separate shared calendars by color. In the past admin assistants were able to separate all the calendars of the attorneys they support by color and in columns, using Exchange 2007 for PC. Now the only way to distinguish between calendars is by selecting the calendar you want to see from the calendar list on the left, causing the calendar events to highlight with a darker shade of the default gray all shared calendars are assigned.
The fonts are a whole separate issue which I've researched exhaustively and found nothing to indicate that there is any way to fix this currently. The older users have on their own gone about decreasing their screen resolution and increasing the default font size at the system level.
Is there any support avenue within MS to or Apple to help with this? Apple has been useless, I've tapped into the Apple Consultants Network and they too are unaware of how to resolve these issues. Does MS have a support vein for Outlook 2011 users on an Exchange 2010 server?

Similar Messages

Exchange 2010/Outlook 2010 Security Alert (...there is a problem with the site's security certificate.)

I've been looking to resolve this issue for a while now and was hoping someone could help me understand my options.
We have Exchange 2010 & Outlook 2010 in our environment. I've created a SSL cert for our ActiveSync from a reputable CA and unfortunately, as you may not be surprised, we are seeing an alert each time we open Outlook that states:
"Security Alert; 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 name on the security certificate is invalid or does not match the name of the site."
Of course my internal server name does not match my external server name. So the SSL I had created for use with OWA and ActiveSync is rejected by my internal Outlook clients.
After doing some research I believe this is related to the Autodiscover service being configured with my internal server name and not my external name.
I've found some info about adding New-AutodiscoverVirtualDirectory and Set-ClientAccessServer commands and then found this article that might help. (Configure
Outlook Anywhere to Use Multiple SSL Certificates) but nothing is specific to my configuration and I'm concerned about what will happen to my existing configuration if this fails.
What happens when you run Set-ClientAccessServer? Does it retain and keep the old server config in place and add a new one or does it wipe it out? Will all of my devices need to be reconfigured?
Same with New-AutodiscoverVirtualDirectory. Does this simply add another virtual directory or is it going to overwrite my existing config?
Then there is the question of whether or not any of this will actually address my issue at all.
absolutezero273c

Sorry.
"[PS] C:\Windows\system32>Set-ClientAccessServer -Identity MailExt -AutoDiscoverServiceInternalUri "https://MailExt
.contoso.com/autodiscover/autodiscover.xml"
The operation couldn't be performed because object 'MailExt' couldn't be found on 'DomainController2.contoso.local'.
+ CategoryInfo : NotSpecified: (0:Int32) [Set-ClientAccessServer], ManagementObjectNotFoundException
+ FullyQualifiedErrorId : 4D980455,Microsoft.Exchange.Management.SystemConfigurationTasks.SetClientAccessServer"...is the error I get.
I've created the split zones and populated the Forward Lookup Zones as follows:
CONTOSO.COM
MailExt(CNAME)MailInt.contoso.local
_tcp _autodiscover(SRV)MailExt.contoso.com
CONTOSO.LOCAL
MailInt(A)192.168.1.10
MailExt(CNAME)MailInt.contoso.com
One thing I did notice is that there isn't a _tcp _autodiscover entry for MailInt in my Forward Lookup Zones. It was recommended that I make that entry for _tcp _autodiscover(SRV)MailExt.contoso.com in another post I read somewhere.
I believe what I am trying to do is create a new autodiscover object as is shown here:
I see there is a Get-ClientAccessServer & Set-ClientAccessServer command but I need to add a CAS. Does the Set-ClientAccessServer add or simply modify?
Or would that require the New-AutodiscoverVirtualDirectory command? I read
this page that discussed creating new virtual directories but that seemed a little risky without knowing all the ins and outs of how this service functions and to what degree this would affect the existing configuration.
I was able to use the Set-ClientAccessServer command and change the actual internal autodiscoverUri to https://MailExt.contoso.com/autodiscover/autodiscover.xml but the name still says MailInt and I continue to get the SSL cert warnings because it is looking
at MailInt.contoso.local.
absolutezero273c

"Resend" option is not working for specific user. "The Operation Failed" Exchange 2010 Outlook 2013

Hi Everybody. I have a weird one for you.
I have a user that gets an "operation failed" message whenever trying to use the "resend" option on any email (It's the one right under recall). I had tested up and down on her machine. Exchange 2010 Outlook 2013
Ran in safe mode, recreated her profile, disabled virus scanning, repaired office. (weird, the font just changed sizes on me)
After all of this I tested on other computers, other users seem to be able to "resend" just fine. However her account does not work on any computer I try, internal or external to the network.
It looks more like a profile issue.
She's a very active archivist, so she only has 486MB of space used by her mailbox.
It's well under quota.
It's been really puzzling me.
MCSE 2003, Exchange. MCTS Vista, 7. Administrator of awful, neglected website http://timssims.net

Hi Timssims,
Since there is only one user in the org has this issue, it seems an issue on the Outlook client side.
I suggest asking Outlook Forum for help so that we can get more professional suggestions.
For your convenience:
https://social.technet.microsoft.com/Forums/office/en-US/home?forum=outlook
However I also have some suggestions for your reference:
1. If this issue occur on Cached Mode, I suggest turning to Online Mode for testing.
2. Please also paste the detailed error message if "operation failed" is not the
complete information.
3. If still not works after perform operations above (including suggestions from Outlook Forum), I suggest re-creating a new mailbox for the specific user just as Martin suggested.
Thanks
Mavis
Mavis Huang
TechNet Community Support

ISA 2006 publish Exchange 2010 Outlook Anywhere with KCD/NTLM and IPSEC - Problem

Hi
I have setup ISA 2006 to publish Exchange 2010 Outlook Anywhere with Kerberos Constrained Delegation and IPSEC.
The clients have an IPSEC policy pushed to them via GPO. The clients are windows 7 laptops and the ISA server is server 2003, so the IPSEC connection is IKE not AuthIP.
However, it seems that the connection will work for a while, then all of a sudden stop working with zero trace of why. I cant get the Oakley log to work and I cant see any traffic on the ISA.
I am wondering if I need to publish the CRL's externally? Currently we don't, and the Outlook Anywhere uses private certificates (as the whole point of IPSEC is to validate the internal certificate, there is no point in using
public certificates).
I have tried using the StrongCRLCheck=0 registry key in the IPsec Policy Agent on the windows 7 machine but it doesn't seem to make a difference.
Any advice would be appreciated.
Steven

Hi,
Firstly, have you received any related error messages in ISA server or on the clients' side? Besides, as you mentioned IPsec, did you have a VPN connection?
In addition,
While ISA 2006 only includes a Client Access Web Publishing Wizard for both Exchange 2003 and Exchange 2007. Which Exchange version you have chosen when publishing Exchange 2010?
Please also make sure that you have selected the
External interface for the web listener to listen on.
Besides, the link below would be helpful to you:
OWA publishing using Kerberos Constrained Delegation
method for authentication delegation
Best regards,
Susie

Exchange 2010 & Outlook 2010 - Cached Mode "okay" work well for you?

Hi All,
On our Client Laptops/PCs we disabled cache mode a long time due to issues experienced with a combination Delegates and Cached Mode occasionally affecting Calendaring. We'd end up with vanishing appointments, etc.
What I'd like to know from you is if you've had a positive experience with Exchange 2010 & Outlook 2010 32bit. If you could impart any gotchas, etc. Our environment is fairly vanilla with a total of 1500 Users.
Thank you very much for your time,
Mr Mister

Hi,
I am using myself outlook 2007 over than WAN (VPN) connection with Exchange 2010 SP2 with about 3 GB mailbox and i personally have not faced any issues. Also, we have about 600 usres with more than 2 GB mailboxes using Outlook 2010 in online mode and
there are not many issues other than email with rich text format with screen shots attached in the mail body causing outlook hang. if we use the same email in html then no issues.
It all depends on the sizing of your CAS and mailbox servers and also on the NIC speed configured on the server. I personally feel that we should have NIC card set to 1GB on the servers also the backup and replication should be on seperate dedicated LAN.

Hello! How can i setup and what to enable that my secretary has my shared calendar on her Iphone and that she can edit it? We are on Exchange 2010, Outlook 2010, Iphone 4s. Can it be done through some app? Thank you!

Hello! How can i setup and what to enable that my secretary has my shared calendar on her Iphone and that she can edit it? We are on Exchange 2010, Outlook 2010, Iphone 4s. Can it be done through some app? Thank you! I'm trying to avoid creating my exchange activesync account on her Iphone and then sync only my calendar.

Thank you for your time. I'm trying to avoid that because she can then simply turn on mail syncronization and then she could read my mail. Another reason is our password policy, that enforces changing our windows logon password every 90 days. Of course changing windows logon passwords demands changing exchange account logon info (password) on Iphone. I have read somwhere that there was an app but it was removed from app store. Any other suggestions would be appreciated.

Exchange 2010 / Outlook 2010 /Outlook 2013 spam filtering

Hi,
We use Exchange 2010 Mailserver and MS Outlook 2010/2013 mail clients. I'm quite confused about configuring junk mail filtering, so can somebody give me few simple answers.
If i'm not wrong basically it goes like that:
Filtering can be made on server/mailbox level, when it can be configured using Exchange powershell. The other way is MS Outlook Junk filtering and it can be configured using GPO.
My first question is, are those two ways completely separated or not? I have found articles which are conflicting in my opinion. For example this speaks how to configure Outlook junk filtering using powershell which should not be possible. Or does Outlook
mean OWA in this example?
http://beccabits.com/2011/10/07/how-to-bulk-modify-safe-senders-list-in-outlook-with-exchange-management-shell/
Second question is if i configure MS Outlook Safe Senders list i can see changes using Exchange powershell which means that mailbox junk filtering can be configured through MS Outlook. Is this correct?
Third question concerns MS Outlook safe senders list which i try to load from txt-file using GPO. Problem is that it works only some users. Checked the situation using process monitor and looks like Outlook reads only junkmailimportlists reqkey and
not the other keys, for example junkmailsafesendersfile. Reqkeys have been loaded from GPO correct anyway. I have tried to fix this and sometimes the only way looks to be updating junkmail settings through OWA and sometimes update-safelist from powershell.
I have tried to update all users safelist using powershell but it doesn't work. How to fix this? We have thousands of users and fixing one by one is not the solution
Thanks in advance
Tried a little more now. Looks like only updating Junk mail list trough OWA helps the situation, when Outlook SafeSenders list do not update using GPO. After using OWA, Outlook GPO works.
Using OWA is not the solution as i said before but is it possible to do the same thing by for example adding some address to every users mailbox safe senders list using powershell? That updates users safelist like OWA do or am i wrong?
~ Jukka ~

Hi Jukka,
Based on my knowledge, Outlook Junk filter is only working on the Outlook client side.
The emails have passed the Edge/Hub server and delivered into MBX server, if the emails matched the Outlook Junk filter conditions, they moved into Junk E-mail Folder directly.
If we don't want the junk e-mails or spams delivered into our Exchange server, we can enable the Anti-Spam and Antivirus in Exchange 2010.
More details in the following articles:
Understanding Anti-Spam and Antivirus Functionality
http://technet.microsoft.com/en-us/library/aa997658(v=exchg.141).aspx
Overview of the Junk Email Filter
http://office.microsoft.com/en-us/outlook-help/overview-of-the-junk-email-filter-HP010355048.aspx
Change the level of protection in the Junk Email Filter
http://office.microsoft.com/en-us/outlook-help/change-the-level-of-protection-in-the-junk-email-filter-HP010356454.aspx
Thanks
Mavis
Mavis Huang
TechNet Community Support

ISA 2006 publish Exchange 2010 Outlook Anywhere with Kerberos Constrained Delegation

Hi,
I have two Exchange 2010 Sp1 CAS with Windows Network Loadbalancing. I set up an alternate Serviceaccount and mapped the http,ExchangeMDB,PRF and ExchangeAB SPNs.
Then i published the Exchange Services via ISA 2006. OWA is working using Internet -> via NTLM -> ISA(webmail.domain.com) -> via KCD -> CAS-Array(ex2010.domain.com)
I tried the same with Outlook Anywhere (RPC over HTTP) without success.
Authentication to the ISA via NTLM works fine, but i think the isa server cannot delegate the Credentials successfully to the CAS-Server.
The ISA Log looks like:
Allowed Connection ISA 24.11.2011 15:50:40
Log type: Web Proxy (Reverse)
Status: 403 Forbidden
Rule: Exchange 2010 RPC
Source: Internal (172.16.251.33)
Destination: (172.18.10.182:443)
Request: RPC_OUT_DATA
http://webmail.domain.com/rpc/rpcproxy.dll?ex2010.domain.com:6001
Filter information: Req ID: 108b89d8; Compression: client=No, server=No, compress rate=0% decompress rate=0%
Protocol: https
So i always get a 403 Forbidden from the CAS.
I the IIS logfile from the cas server i see this entry:
2011-11-24 15:51:37 172.18.10.182 RPC_OUT_DATA /rpc/rpcproxy.dll ex2010.domain.com:6001 443 - <ISA IP> MSRPC 401 1 2148074254 203
I use the same Listener for OWA and Outlook Anywhere. Authentication Methods are Basic and Integrated. I forward the request to a webfarm which exists of the two physical CAS. Internal Site Name is set to the NLB name ex2010.domain.com, SPN is set to http/ex2010.domain.com
Thanks for your support

Hi, i ran into the same Problem.
the steps above solved mine too (Creating a custom AppPool which runs under LocalSystem).
I wonder why they included only the Script: convertoabtovdir.ps1
http://social.technet.microsoft.com/Forums/en-US/Forefrontedgegeneral/thread/dc24ccd3-378a-47cc-bbbf-48236f8fe5b0
Ist this a supported configuration (changing AppPool of RPC)?

Releasing HDD space after moving exchange 2010 (SBS 2011)to Office 365

Hello, I have completed a cut over install to Office 365(email only) form SBS 2011(Exchange 2010). Everything is working perfectly. The customer would like to recover the disk space used by the on premis exchange 2010.
Normally i would just disable Exchange on the SBS server and leave it at that but is there a way to remove all of the mailboxes and/or the database to recover the disk space used by exchange. I know unisntalling exchange is a bad idea on SBS 2011 so would
like some other options.
Thanks

Hi
If you manually setup an outlook profile and enter in all the settings does it work?
In you local DNS you still have an autodiscover record for your local exchange server? Correct?
Hope this helps. Please remember to click “Mark as Answer” on the post that helps you, and to click “Unmark as Answer” if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.

Exchange 2010, Outlook 2010, some clients receive "server unavailable" when logging into outlook

We have a single exchange 2010 server running hub, cas, and mailbox as a virtual machine in VM 5. Currently on version 14.3 build 123.4 running on Server 2008 R2. Clients connecting to this server are all running Outlook 2010 with a mix of OS between
xp and win 7. Domain controllers are all 2003 sp2. We have a multi-campus environment with most users accessing across a WAN connection (mpls and metro-e). Quota Limits of 1gig imposed on all mailboxes. We do still
have a Exchange 2003 server that we are completing the migration of users off of in our environment. But all mailboxes on exchange 2010 are accessed thru Outlook 2010. Migration from 2003 to 2010 happens only after Office 2010 is installed.
We are a little over 50% migrated - (~750 users, 1100 entities)
I have some 2010 clients complaining that they receive "the server is unavailable" when launching outlook for the first time in the morning. A second time it usually opens. This happens for remote WAN and local LAN users. Also,
during the day as outlook is open, when trying to open an email or navigate between folders in the inbox they will also have outlook stop responding as it tries to contact the server.
Monitoring the server - CPU averages 40-50% thru the day with spikes in the 75-100%. Usually the processes that spike are Store.exe or msftefd.exe.
I have verified that IPV6 is disabled on the exchange server - and it doesn't exist on the 2003 DC's. Searching for answers keeps turning up results for OOF or Outlook 2003 RPC. Neither are the case here.
Would we benefit from adding a 2nd server into our environment? If so - hub? Cas? which would be better to offload off the primary?
or is there a better way to handle this issue?

Hi,
According to your description, the issue happens on every morning. Thus, it’s mostly likely caused by that there are too many sessions bringing the performance issue.
To confirm it, we can use performance monitor to check the following counters when Outlook works slowly:
RPC request, RPC average latency and RPC operation/sec
http://technet.microsoft.com/en-us/library/dd335215(v=exchg.141).aspx
If you have any question, please feel free to let me know.
thanks,
Angela Shi
TechNet Community Support

Configuring Message Clasifications Exchange 2010 - Outlook 2007/2010/2013

Hi
I created Message Classification as described in:
http://technet.microsoft.com/en-us/library/bb123498(v=exchg.141).aspx
New-MessageClassification ....
New MessageClassification is visible in OWA.
I stared deploy Message Classifications for Outlook 2007 using this
http://technet.microsoft.com/en-us/library/aa998271(v=exchg.141).aspx
Of course there is small bug: "AdminClassificationPath"="c:\\Classifications.xml" but is should be
"AdminClassificationPath"="c:\Classifications.xml"
After set up it doesn't work. The same for Outlook 2010 and 2013?
Does anybody deploy Message Classifications for Outlook 2007 or 2010 or 2013 with success?
I use Exchange 2010 SP3 with all RU and Outlook 2007, 2010, 2013 with all updates.
Kind Regards Tomasz

Hi,
How do you know this is an old reoccurring message? Based on the content or time?
Since the MailboxAutoReplyConfiguration is correct, I suspect the issue can occur by certain client machine. At this stage, I suggest you disable OOF and re-enable
OOF on the problematic machine. If the issue persists, please refer to the following article to clean the problematic client’s Outlook rules. (run Outlook.exe /cleanrules in Run console.)
http://www.tech-recipes.com/rx/2161/outlook_2007_clean_up_command_line_switches/
Thanks.
Novak Wu
TechNet Subscriber Support in forum
If you have any feedback on our support, please contact
[email protected]
Please remember to click “Mark as Answer” on the post that helps you, and to click “Unmark as Answer” if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.

Send As Permissions - Exchange 2010 - Outlook 2013

I am currently having an issue with an account. 2 people share an Admin Account inbox, while having their own inbox, Although the Admin mailbox only works in Online
mode or the folders will not update and emails will not come through.
This is not the problem though.
Before today both people were working fine for the last few months. Now User 1 (only user to send as Admin mailbox) can not send as the mailbox, while
in online mode. In cached mode it works fine, however the folders do not work.
When in online mode, i can remove the address from the From: drop down and re-add, however this only works for that email. Sending another email reaches
the same error "you do not have the permission to send as blah blah blah". This is a popup error.
Removing the address and re-adding works every time, however as you can imagine, this is not ideal for the user. In testing I have removed permissions
for send as in EMC but removing the address from the from field and re-adding is still allowing it to send. It seems outlook/exchange is not recognizing the permissions. Does anyone have any ideas on what could be causing this?
Exchange version is 2011
Outlook version is 2013

In testing I have removed permissions for send as in EMC but removing the address from the from field and re-adding is still allowing it to send. It seems outlook/exchange is not recognizing the
permissions. Does anyone have any ideas on what could be causing this?
Hi,
After removing the permissions in EMC, I suspect it still takes some time to take effect. We can verify this by sending as the Admin mailbox on OWA to check the result. Then wait for some time, send the test email in Outlook again.
This issue is actually opposite to these issues I've seen before: Most other issues are that the user is not able to send as another user in Cached mode, but able to send in Online Mode. Your description kind of implies there's something interfering
with the connection between Outlook and Exchange when Outlook is in Online Mode, please disable all suspicious add-ins in Outlook, especially the anti-spam add-ins provided by the anti-virus program. Then disable the anti-virus program and the firewall temporarily
to check the result.
As mentioned in your post, this issue is also related to the Auto-Complete List in Outlook, the list may have been corrupted. We can try clearing the list to check if the problem persists:
In Outlook 2013, click FILE -> Options -> Mail -> Send messages -> Click "Empty Auto-Complete List" button -> Yes -> OK.
Regards,
Melon Chen
TechNet Community Support
It's recommended to download and install
Configuration Analyzer Tool (OffCAT), which is developed by Microsoft Support teams. Once the tool is installed, you can run it at any time to scan for hundreds of known issues in Office
programs. 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]

Exchange 2010\Outlook Mail issues

Hi,
I am having some issues with mail disappearing and outlook not updating. The issues are:
When sending an email from Outlook it appears in the sent items for 30 seconds in Outlook and then disappears. It never shows up in OWA The email does send though. If an email is sent via OWA the email appears and stays in both OWA and Outlook. This is
happening in Outlook 2010\Exchange 2010
Updating issues on random folders in Outlook. This is happening on both Outlook 2013 and Outlook 2010 different users with the same Exchange 2010 back end.
Both users have cached email forced. I have tried rebuilding the mailbox locally.
Cheers,
Zac Avramides

Hi,
Thanks for your detailed information about the symptom.
It seems the issue is more related to the Outlook client since OWA works fine. I suggest we can follow the checkpoints below:
1. Rebuild Outlook profile.
2. Disable any third-party firewall or AV programs.
3. Run Windows in Clean Boot.
4. Run Outlook in safe mode by “Outlook /safe”.
What’s the result now?
Thanks,
Please remember to mark the replies as answers if they help and unmark them if they provide no help. If you have feedback for TechNet Subscriber Support, contact
[email protected]
Simon Wu
TechNet Community Support

Exchange 2010 - Outlook Anywhere trying to connect to internal server name first before connecting to proxy server

Hello,
I have an Exchange 2010 question which I will post in the Exchange 2013 section since the Ask a question button in the legacy Exchange Servers section of technet takes me back to the part of Technet where I can only ask questions regarding Exchange 2013.
If someone can point me to a part where I can place a question in an Exchange 2010 forum please let me know.
We have Exchange 2010 setup with a CAS array listening to outlook.internaldomain.com
We have TMG 2010 setup with a rule for Outlook Anywhere, the rule listens to mail.externaldomain.com and traffic that meets this rule is let through to outlook.internaldomain.com.
When I fire up my laptop, which is connected to the internet, and start Outlook and let it configure my profile through autodiscover it sets it up correct and fills the Outlook profile with a servername stating outlook.internaldomain.com and a proxyserver
to be used stating mail.externaldomain.com. After initial setup when my Outlook starts it almost immediatly prompts me for a username and a password so this is working fine.
At the office we have an internal network segment where DHCP is servicing the connecting clients and giving them our internal DNS servers because they need connection to some other network segments which are not available to the internet. This network segment
does not have access to our internal Exchange environment but has full access to the internet. Clients in this network segment do want to use Outlook so using Outlook Anywhere for them is the logical way to go. When I connect my laptop to this network segment
I get handed an IP address and our internal DNS servers, when I start Outlook it takes about two minutes before a the credential prompt pops up and another 2 to 6 minutes after entering credentials before it says all folders are in sync. This is quite long
and our clients find this unacceptable.
I started testing what might be going on here and I have found that when I manually enter external DNS servers the Outlook password prompt will popup in seconds and all is working as expected so it seems Outlook is trying to connect to the internal servername
when using our internal DNS servers (which can resolve outlook.internalnetwork.com) instead of directly going to the proxy server which is to be used for Outlook Anywhere.
When I start a network monitor trace my thoughts are confirmed because when I am connected to the internal network segment OUTLOOK.EXE first tries to connect to outlook.internaldomain.com, it almost immediately gets a response stating that this route is
inaccessible but OUTLOOK.EXE keeps on trying to connect untill some sort of time out is reached (somewhere around two minutes) after which it connects to mail.externaldomain.com and Outlook shows the credential prompt.
So to round it up, when connected to DNS servers that can resolve the internal servername Outlook tries to connect to the internal servername in stead of the external name, Outlook does not reckognize the answer from the network that the internal route is
not acessible (or it does but does nothing with this information).
Has anybody experienced this behaviour in Outlook?
Does anyone have a solution in where I can force Outlook to connect to it's proxyserver and disregard the internal servername?

Thank you for your reply.
The client computers that are experiencing the issues are not domain joined, the only reason I can think of why this is occurring is because the DNS servers are able to resolve the internal hostname of the server, but I would expect Outlook to always use
the proxy server that has been set in the configuration of the Outlook profile. Or at least acknowledging the answer that the initially tried route is inaccessible and immediately continue to the proxy server.
For setting the same hostname for internal and external use, we use different namespaces internally and externally, do you mean setting the external hostname on the CAS array for internal use ? Wouldn't that push all internal communication to the internet
and to the outside interface of the TMG where the server is published with that hostname ?

Exchange 2010 / Outlook 2010 "client error in synchronization log"

Exchange
2010:
Error
in Synchronization Log
19:28:32 Error synchronizing
folder
19:28:32                               [8004010F-501-8004010F-0]
19:28:32                               The
client operation failed.
19:28:32                               Microsoft
Exchange Information Store
19:28:32                               For
more information on this failure, click the URL below:
19:28:32                               http://www.microsoft.com/support/prodredirect/outlook2000_us.asp?err=8004010f-501-8004010f-0
Please
assist with this error. Is it serious? The URL provided does not offer nor reflect any worthwhile information. Thanks.

The error means that the client hasn’t located the resource it’s looking for
Does the error appear on all outlook clients?
Do you use organizational forms library? (KB
933358)
The error can be caused by incorrect permission on the “EFORMS REGISTRY”, so please run the cmdlet below to check the permission on
the Default group, the permission should be “Reviewer”
Get-PublicFolderClientPermission “\NON_IPM_SUBTREE\EFORMS REGISTRY”
Per my research, you can avoid this error by removing all the subfolders in the “EFORMS REGISTRY” folder, if you don’t use organizational
forms library. But, please use the Get-PublicFolderStatistics cmdlet to verify that no items under the “EFORMS REGISTRY” folder before. And, if the error still appears, please remove the OST file and then recreate the mail profile
Please run ExBPA against the exchange servers for health/permission check
Notes: If forms library replicas are added to Exchange 2010 servers, 80004005-501-4B9-560
will appear in the sync message, yet it can be safely ignored
Resources:
“The Organizational Forms Library has been deleted and re-created after the .ost file has synchronized the library” section
in You receive an error message when you try to synchronize your offline folder file if the Organizational Forms Library on your Exchange computer has
been re-created or cannot be located
James Luo
TechNet Subscriber Support (http://technet.microsoft.com/en-us/subscriptions/ms788697.aspx)
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Exchange 2010/Outlook 2011 woes

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