Exchange 2013 Mail Flow Through VPN

I have 2 Exchange servers in 2 different AD sites. Is it possible to route mail flow between the 2 sites through a VPN tunnel? I want to force mail flow between the 2 servers to route externally through the internet.
Appreciate any feedback.

Hi Chester,
we have a DNS record for mail and this record is pointing to our private IP address of CAS server. Network team has done network configuration for that particular IP to route the traffic through VPN tunnel to the Exchange servers in other site. Another thing
for you to think is Private IP request won't go to internet and will go to DNS server in that site and once the DNS server will resolve that request against IP address the traffic will be routed to that server.
Kindly mark this as answer if found helpful. Thanks.
Regards, Riaz Javed Butt | Consultant Microsoft Professional Services MCITP, MCITP (Exchange), MCSE: Messaging, MCITP Office 365 | msexchgeek.wordpress.com

Similar Messages

Exchange 2010 to Exchange 2013 mail flow?

We are planning to migrate Exchange 2010 to Exchange 2013.
I understand that we need to upgrade the CAS to 2013 for Internet Facing.
What about mail flow. Currently, Internet mail flows to Exchange 2010 (single site). Can I keep it for sometime after introducing 2013 and do the cutover of HUB once all the mailboxes are moved to 2013? Or I have to get the mail flow to 2013 first.
Also, how does HUB 2010 transfer mail or receive mail from 2013? Does it get from the CAS proxy in 2013 or from HUB?
Thanks!!!

Yes, you can. But my preference is to move the mail routing early in the migration, usually even before moving mailboxes, because I believe it reduces the risk of a service interruption.
I believe it goes through the front-end transport on the CAS, since that is the TCP port 25 service.
Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

Exchange 2013 mail flow problem

Hello!
We have problem, could not send mails via Exchange 2013 server.
Symptoms:
-no messages in message queue
-if sending mail to this domain, the message seems sent at Sender.
-if sending mail from this domain, the messages are in the mailboxes' DRAFT folder
Here are some SMTP logs:
2013-04-03T20:52:25.448Z,Inbound Proxy Internal Send Connector,08CFFEB14C28BE2C,10,192.168.3.2:26408,192.168.3.2:2525,<,250-STARTTLS,
2013-04-03T20:52:25.448Z,Inbound Proxy Internal Send Connector,08CFFEB14C28BE2C,11,192.168.3.2:26408,192.168.3.2:2525,<,250-AUTH NTLM,
2013-04-03T20:52:25.448Z,Inbound Proxy Internal Send Connector,08CFFEB14C28BE2C,12,192.168.3.2:26408,192.168.3.2:2525,<,250-8BITMIME,
2013-04-03T20:52:25.448Z,Inbound Proxy Internal Send Connector,08CFFEB14C28BE2C,13,192.168.3.2:26408,192.168.3.2:2525,<,250-BINARYMIME,
2013-04-03T20:52:25.448Z,Inbound Proxy Internal Send Connector,08CFFEB14C28BE2C,14,192.168.3.2:26408,192.168.3.2:2525,<,250 CHUNKING,
2013-04-03T20:52:25.448Z,Inbound Proxy Internal Send Connector,08CFFEB14C28BE2C,15,192.168.3.2:26408,192.168.3.2:2525,*,,"EHLO options between current server and proxy target do not match : Xrdst, . Critical
non matching options : Xrdst, . Failing over."
2013-04-03T20:52:25.448Z,Inbound Proxy Internal Send Connector,08CFFEB14C28BE2C,16,192.168.3.2:26408,192.168.3.2:2525,>,QUIT,
Software Enviroment:
-Windows Server 2012 Server Standard
-Exchange Server 2013
-fully patched system (includes the brand new Exchange 2013 CU1), the error was realized before this update.
Regards.
molni

Hi
Can you run ipconfig/flushdns or create hosts file recorder?
Terence Yu
TechNet Community Support

Exchange 2013 Mail flow rule using RegEx

We're trying to implement a rule on certain mailboxes that it shouldn't accept an email without a subject.
I found documentation from Microsoft on exchange 2010 to Configure
a Transport Rule for Messages That Have a Blank Subject, but I tried using the ^$ RegEx
with Exchange 2013 and it doesn't seem to work.
I also looked at the Transport
Rule Predicates for Exchange 2013 and it clearly says thatSubjectMatchesPatterns
matches messages where text patterns in the Subject field match a specified regular expression.
My workaround was to reject all messages to those specific mailboxes except if subject pattern matches. but
if I want to add now conditions ie. to reject emails with a subject "Sent from my snipping tool" I can't do it.
I found Here that
Exchange 2013 now supports extended RegEx but I didn't find that the syntax for ^$should
be any different in extended RegEx.

If you use any special character in the RegEx you must use
\m Escape m, where m is one of the meta characters described above: ^, ., $, |, (), [], *, +, ?, \, or /.
as decribed in http://technet.microsoft.com/en-us/library/jj674702%28v=exchg.150%29.aspx

Cross-Site Mail Flow Through Internet

Hi,
I have typical Exchange 2013 servers deployed in 2 AD sites. Currently, mail flow between the 2 sites are going through our WAN. Is there a way to force mail flow between the 2 sites to go through the internet?

Hi Chester,
Create send connector pointing to the internet gateway or edge server for each AD site Exchange server separately and on the default receive connector instead of all ip address ..customize to the exchange server specific ip address that are located in the
same site...this will not allow the mail flow across the WAN and it uses the internet route for mail routing across the site..
Exchange Queries

Querying Exchange 2013 Mail server for email items using c# and Exchange Web Services

I am trying to upgrade an existing application that reads Exchange 2003 using WebDAV. The mail server is to be upgraded to Exchange 2013, so I am checking how I can use EWS.
I have a problem in that although I know the inbox has unread items with attachments, the query I am running against the
FindItems object is returning empty (results.totalCount=0)
Here is my code snippet:
private static void GetAttachments(ExchangeService service)
// Return a single item.
ItemView view = new ItemView(100);
ServicePointManager.ServerCertificateValidationCallback = CertificateValidationCallBack;
ExchangeService service = new ExchangeService(ExchangeVersion.Exchange2010_SP2);// .Exchange2007_SP1);
service.UseDefaultCredentials = true;
service.AutodiscoverUrl("[email protected]", RedirectionUrlValidationCallback);
ItemView view = new ItemView(1);
string querystring = "HasAttachments:true Subject:'ATTACHMENT TEST' Kind:email";
// Find the first email message in the Inbox that has attachments.
// This results in a FindItem operation call to EWS.
FindItemsResults<Item> results = service.FindItems(WellKnownFolderName.Inbox, querystring, view);
//FindItemsResults<Item> results = service.FindItems(WellKnownFolderName.Inbox, new ItemView(50));
if (results.TotalCount > 0)
// looping through all the emails
for (Int16 iDx = 0; iDx < results.TotalCount-1; iDx++)
EmailMessage email = results.Items[iDx] as EmailMessage;
if (email.IsRead == false) {
// Request all the attachments on the email message. This results in a GetItem operation call to EWS.
email.Load(new PropertySet(EmailMessageSchema.Attachments));
foreach (Attachment attachment in email.Attachments)
if (attachment is FileAttachment)
FileAttachment fileAttachment = attachment as FileAttachment;
What I am supposed to be doing is reading all the unread emails in the target inbox (only one Exchange server) and taking the attachments on disk so I can then add them as attachments as new cases on SalesForce.
Where am I going wrong?
Also, this line:
ItemView view = new ItemView(100);
was:
ItemView view = new ItemView(1);
Surely that will only look for one email item, right?

thanks, do you know why I would be getting an error message like 'The specified object was not found in the store'
here is my code:
ServicePointManager.ServerCertificateValidationCallback = CertificateValidationCallBack;
ExchangeService service = new ExchangeService(ExchangeVersion.Exchange2010_SP2);// .Exchange2007_SP1);
service.Url = new Uri("https://sgexc.bocuk.local/EWS/Exchange.asmx");
//creates an object that will represent the desired mailbox
Mailbox mb = new Mailbox(@"[email protected]");
//creates a folder object that will point to inbox folder
FolderId fid = new FolderId(WellKnownFolderName.Inbox, mb);
//this will bind the mailbox you're looking for using your service instance
Folder inbox = Folder.Bind(service, fid);
FindItemsResults<Item> findResults = service.FindItems(new FolderId(WellKnownFolderName.Inbox, new Mailbox("[email protected]")),new ItemView(10));
it's happening on this line:
Folder inbox = Folder.Bind(service, fid);
and if I try to use AutoDiscoverURL then I just see my own inbox.

Exchange 2013 Mail Receiving Issues

Hi everybody,
Yesterday I configured a new DC and Exchange on Hyper-V (Server 2012 and Exchange 2013)
All functions and rolls are configured and installed but i am having issues receiving external e-mails.
Almost all of the external mails are being deliverd a half hour to a hour after being sent.
To start of on the first level.
I got a Siemens Fiber modem with an external address connected to the WAN of my Draytek 2995 router.
Alle the needed ports are forwarded to the Draytek (80,443,25,1723).
The Draytek DHCP function is set to off.
192.168.168.2 (DC) -> 80 (HTTP IIS)
192.168.168.2 (DC) -> 1723 (RRAS)
192.168.168.3 (Exchange) -> 25 (SMTP)
192.168.168.3 (Exchange) -> 443 (SSL)
My Draytek router is connected through LAN1 to a HP switch (unmanaged).
The physical server has 3 NIC's, all of these are connected to the HP Switch
I Disabled Hyper-V Queuing on the NIC's because this causes an issue with slow network connections.
The network has been configured as following.
I configured the Server 2012 R2 on the hardware(physical server) with only the Hyper-V roll.
NIC1is setup for the physical server,
IP Address: 192.168.168.1
Subnet: 255.255.255.0
Gateway: 192.168.168.254 (Draytek address)
DNS: 192.168.168.254 (Draytek address)
The Server software firewall has been set to a private network through the local security policy.
I have setup 2 VM's through the Hyper-V roll.
The first VM is the Server 2012 R2 Domain controller.
For this VM I created a virtual switch connected to my second NIC(2).
I unchecked the box where my host can communicate with the NIC(2).
The DC has been configured as following:
Hostname: SERVER
IP Address: 192.168.168.2
Subnet: 255.255.255.0
Gateway: 192.168.168.254
DNS: 127.0.0.1
I can ping to all the adresses from this server (internal and external).
The server has been promoted to domain controller with the following rolls.
ActiveDirectory, Certificate Autohority, DHCP, DNS, RRAS, RDP.
Alle these rolls have been set and working. (all have been tested)
DHCP has all options configured (scope, router-192.168.168.254, dns-192.168.168.2)
A DNS simple and recursive test work fine.
I did no configuration on the DNS after the DC PROMO.
So i created users in the AD.
After that I created a second VM, this one is used for the Exchange.
I setup a second virtual switch connected to NIC3 and installed Server 2012 R2 with the following config.
Hostname: SERVER
IP Address: 192.168.168.3
Subnet: 255.255.255.0
Gateway: 192.168.168.254
DNS: 192.168.168.2 (pointing to the DC)
I joined this server to the domain, everything is working fine.
Both servers have internet and network.
Running portscans on 1723 and 80 all work like a charm.
No its time to install Exchange.
I ran all the prerequisits and PowerShell commands (IAcceptLicense. etc.)
Installed de needed API and filters.
Installed Frameworks 3.5 on both servers.
And the Exchange installation was succesfull.
CU3 is also installed.
I configured the send connector, accepted domains etc.
Created all needed certificates (self signed)
Did a portscan on 433 and 25 and they work.
All the hosting records are set mail.domain.nl etc. and MX records.
I created inboxes for the users and was able to connect them to the users in the Active Directory on the DC without any problems.
Connecting through the internet to OWA works perfect and i can login with users.
Sending e-mail internally works perfect, the messages are being deliverd in an instant.
Sending e-mail externally also works perfect, i receive mails in a few seconds on a person email address.
But when i reply or send e-mail to my new Exchange it can take up to hours to receive the mails!
I did online SMTP checks and e-mail checks, the all come out like it should.
One message from MX TOOLBOX on the SMTP:
SMTP Transaction Time
8.408 seconds - Not good! on Transaction Time
I have nog other receive connectors setup, just the standard connectors.
So i got into the Exchange ECP and under "server" i setup the DNS to listen to 192.168.168.2 (DC).
I've read that when this is set to all ip addresses it can cause mail delay, but no luck.
I ran the best practices analyzer and get about 23 errors and 20 warnings.
A lot of services are unhealt like the "ExchangeTransport).
I have no idea what is causing the issues and read almost every forum.
Does anyone have a clue what is going on?
Did i miss something, is there a misconfiguration?
Best regards,
Tim

The mailserver did not receive any e-mails in this timespan, it was not an issue with the connector to the user mailboxes.
The internal e-mail also works flawless.
The entire Exchange server just not received this mail in time.
I sent an e-mail from my personal accout with the option in my outlook to receive a delivery-reply.
I got the reply as soon as the mail was deliverd, this took about a half hour to a hour.
After you asked me about the firewall, i got a hunch..
It had to be on the incomming connection, so i checked every single firewall on the network and disabled them.
Still the same problem...
But there was still one ethernet device that could have a firewall, the internet modem!
This ATM modem receives multiple external IP's from the ISP, so I figured there was no firewall on this device. (Just like all the cable modems that are deliverd in our area by Ziggo(ISP).
But I was wrong, there was a firewall enabled on the modem!
All the ports in the modem had been forwarded but somehow the modem-firewall filtered the traffic,
creating the issue on the incomming e-mail.
I disabled the firewall and all the external e-mails are being received in an instant!
Re-enabled all the software firewalls on the servers and re-enabled the malware filter through powershell, after these steps I did another test, and everything still works like a charm!
Many thanks for your help Kjartan!

Exchange 2013 Mail Size Limits

I am having an issue with setting the max send and receive size on Exchange 2013. I keep getting the following error when I attempt to send a 20 meg file server to an internal exchange account OR if I attempt to send a 20 meg file from the exchange
server to an external account:
#550 5.3.4
ROUTING.SizeLimit; message size exceeds fixed maximum size for route ##
I have checked the mail sizes and below is the report. I currently have both send and receive set to 100MB. Is there some other setting in 2013 that I am not aware of?
AnonymousSenderToRecipientRatePerHour                       : 1800
ClearCategories
: True
ConvertDisclaimerWrapperToEml                               : False
DSNConversionMode
: UseExchangeDSNs
ExternalDelayDsnEnabled                                     : True
ExternalDsnDefaultLanguage                                  :
ExternalDsnLanguageDetectionEnabled                         : True
ExternalDsnMaxMessageAttachSize                             : 100 MB (104,857,600 bytes)
ExternalDsnReportingAuthority                               :
ExternalDsnSendHtml
: True
ExternalPostmasterAddress                                   :
GenerateCopyOfDSNFor                                        :
HygieneSuite
: Standard
InternalDelayDsnEnabled                                     : True
InternalDsnDefaultLanguage                                  :
InternalDsnLanguageDetectionEnabled                         : True
InternalDsnMaxMessageAttachSize                             : 100 MB (104,857,600 bytes)
InternalDsnReportingAuthority                               :
InternalDsnSendHtml
: True
InternalSMTPServers
JournalingReportNdrTo                                       : <>
LegacyJournalingMigrationEnabled                            : False
LegacyArchiveJournalingEnabled                              : False
LegacyArchiveLiveJournalingEnabled                          : False
RedirectUnprovisionedUserMessagesForLegacyArchiveJournaling : False
RedirectDLMessagesForLegacyArchiveJournaling                : False
MaxDumpsterSizePerDatabase                                  : 18 MB (18,874,368 bytes)
MaxDumpsterTime
: 7.00:00:00
MaxReceiveSize
: 100 MB (104,857,600 bytes)
MaxRecipientEnvelopeLimit                                   : 500
MaxRetriesForLocalSiteShadow                                : 2
MaxRetriesForRemoteSiteShadow                               : 4
MaxSendSize
: 100 MB (104,857,600 bytes)
MigrationEnabled
: False
OpenDomainRoutingEnabled                                    : False
RejectMessageOnShadowFailure                                : False
Rfc2231EncodingEnabled                                      : False
SafetyNetHoldTime
: 2.00:00:00
ShadowHeartbeatFrequency                                    : 00:02:00
ShadowMessageAutoDiscardInterval                            : 2.00:00:00
ShadowMessagePreferenceSetting                              : PreferRemote
ShadowRedundancyEnabled                                     : True
ShadowResubmitTimeSpan                                      : 03:00:00
SupervisionTags
: {Reject, Allow}
TLSReceiveDomainSecureList                                  : {}
TLSSendDomainSecureList                                     : {}
VerifySecureSubmitEnabled                                   : False
VoicemailJournalingEnabled                                  : True
HeaderPromotionModeSetting                                  : NoCreate
Xexch50Enabled
: True

Hello Landfish,
Good Day...
The output gives the information that Size limit set for Receive and Send is 100 mb, but setting could have changed. So you can follow the below steps to resolve the issue.
There are basically three places where you can configure default message size limits on Exchange:
Organization transport settings
Send/receive connector settings
User mailbox settings.
To check your server’s current limit you can open Exchange Management Shell
Try the below commands to check the Message quota size limit
get-transportconfig | ft maxsendsize, maxreceivesize
get-receiveconnector | ft name, maxmessagesize
get-sendconnector | ft name, maxmessagesize
get-mailbox Administrator |ft Name, Maxsendsize, maxreceivesize
To change the above size limits based on your requirement.
Set-TransportConfig -MaxSendSize 200MB -MaxReceiveSize 500MB (Size is based on your requirement)
Attachment size limit
To set up the rule you can use the below PowerShell cmdlet, as the method is quite simple
New-TransportRule -Name LargeAttach -AttachmentSizeOver 20MB -RejectMessageReasonText "Message attachment size over 20MB - email rejected."
For More info
https://technet.microsoft.com/en-us/library/bb124708(v=exchg.150).aspx
Remember to mark as helpful if you find my contribution useful or as an answer if it does answer your question.That will encourage me - and others - to take time out to help you Check out my latest blog posts @ Techrid.com

Exchange 2013 - Mail receive problem -Help!

Exchange 2013 SP1 -fresh install -test environment with one test mailbox setup in addition to the Administrator account. Using default Receive Connectors and it is set for Anonymous. Using OWA and Outlook 2010 for testing.
We can send/receive mail INTERNALLY in both Outlook & OWA between our test user and the Administrator user.
We can send mail externally from both accounts.
We are not receiving mail into the Inbox of either OWA or Outlook.
We are not seeing any authentication issues with Outlook -always shows connected to Exchange. But if we have same problem in OWA then we are just testing with it for now.
We ran the Microsoft Connectivity Analyzer for both Inbound and Outbound SMTP and it passed with no errors/warnings L
We did NSLOOKUP, from a Command prompt at the server wtith this result -not sure why it shows server as unknown?:

Thank you for replying. Yes the mailbox is at Time Warner and I can use their webmail interface and see the messages I sent to the test user are there.
No, our domain name is companyname.com (if you need the actual name..I am not sure if I should send it to you?) and we use
[email protected] for email.
Our external A records and MX records are at Network solutions and that is posted here-- but decided to start another thread with more concise information as I learned of it:
http://social.technet.microsoft.com/Forums/office/en-US/0b18e928-0207-4ab9-bc12-c00a75088bdc/new-deployment-outlook-can-send-but-not-receiving-messages?forum=exchangesvrsecuremessaging
When I do NSLOOKUP of our domain I get just the two MX records at Time Warner. Not anything with our actual domain name for email in it. I just added the A records for mail.companyname.com and autodiscover at Network Solutions yesterday...but though those
were only for use externally for OWA, ActiveSync, etc
Note we do not use Split-DNS on our internal domain either. Our AD name is different than our public domain name - The AD is named with a subdomain: qs.companyname.com
Lastly, I did not create an MX record at network solutions for mail.domainname.com. Should I do that and set it to a higher priority?

Exchange 2013 mail domain rewrite

Hi
In exchange 2013 there is no Edge role. So how i can rewrite domain in email message. Exmaple.
User primary smtp is [email protected] when he is sendin mail to out side of organisation email address should be [email protected]
Thanks

Hello,
1. add your domain to accepted domains (mailflow > accepted domains)
2. create new e-mail address policy and add the suffix you want (mailflow > emailaddreepolicies). Do not forget to apply!
3. Done! Send an e-mail to your external address: hotmail, gmail, etc
Good Luck!

Outlook 2013 with Exchange 2013: Mails stuck in Outbox

Hi everybody,
I am using Outlook 2013 connecting an Exchange 2013 server. After sending a mail, all outgoing mails remain in the outbox. After removing the cache files it works for a while until the problem occurs for the next time (approx. once every two days).
I already re-installed Windows 8 to test it on a completely clean environment...OWA works fine, the problem only exists with Outlook.
Additional note: It might be interesting that after sending a mail, the "Send/Receive progress" window states "sending [email protected] - complete" but the Mail is still in the outbox and was not delivered to the recipient. Safe mode doesn't work
for me. Other users connecting with Outlook 2010 don't have a problem with this exchange server.
Do you have any ideas? If I can provide you with further information, please let me know.
Greets,
Basti

Thanks for your answer. Here are the requested information:
>What addins are you using?
No 3rd party addins, at the moment "Microsoft Exchange Add-In", "Microsoft VBA for Outlook Addin",
"OneNote Notes about Outlook Items" and "Outlook Social Connector 2013" are activated. But the problem also occurs if no addin is active (or even in Safemode).
>Antivirus
scanners can prevent Outlook from moving messages to the sent folder.
I will try to deactivate the virus scanner the next time. (Avira is used)
>Can
any address trigger this behavior or does it happen with certain addresses?
No, it does happen with any address by random. Once the problem occurs, I can try to send as much mails as I want to
any address - nothing leaves the outlook client.
>Is
this your mailbox or a shared/secondary mailbox?
It is a user's mailbox, nothing shared.

Exchange 2013 OWA published through TMG: Unable to preview documents with Office Web App server

We configured our Exchange 2013 servers to use Office Web App for document previews on OWA. Everything works fine internally, and externally also when we access OWA directly. But when from an outside network we open a OWA session through TMG and try to preview
a document, we get the error "Sorry we cannot open this document, an error occured . . ."
Did anyone experience such an issue ?
Thanks,
Antonio

Hello,
Since directing accessing OWA from CAS is fine and the issue only occur when involving TMG, I think the issue is more related to TMG settings. Please find more efficient support
via our TMG forum:
http://social.technet.microsoft.com/Forums/en-US/Forefrontedgegeneral/threads
Thanks,
If you have feedback for TechNet Subscriber Support, contact
[email protected]
Simon Wu
TechNet Community Support

Exchange 2013 Mail Enable Existing Security Groups

Hello,
I can't seem to find how to mail enable an existing Security Group in Exchange 2013. Does anyone know how to do this? I have created them as Universal Security Groups in Active Directory. I see that if you create them from the Exchange
Admin Center, it will work, but I have a ton of groups with very complicated memberships that exist in AD and I would prefer not to delete them, recreate them, and adjust membership.
I looked for a cmdlet that would let me do this, but I can't seem to find one.
Does anyone know how to Mail Enable an Existing Group from Exchange 2013?
Thanks

Hello Stewart,
If these groups are universal security groups, you can just follow Martina's suggestion to do that.
Thanks,
Evan Liu
TechNet Subscriber Support in forum
If you have any feedback on our support, please contact
[email protected]
Evan Liu
TechNet Community Support

Migrating Users from Exchange 2007 to Exchange 2013 Without redirection through exchange 2013.

We have all our users and mailboxes on Exchange 2007 and I have introduced two Exchange 2013 servers in my organization and both have mailbox and CAS server installed on them.
With Exchange 2007 server, I had not modified any of the internal and external url/uri and had stayed with the defaults.
For migration most of the documents are suggesting of changing the default internal URL and Auto Discover Service internal URI values.
In my case, I want to migrate all the users and mailbox (everything that is on Exchange 2007) form 2007 to 2013 and decommission exchange 2007 completely from our organization.
I am in the phase of transferring users from Exchange 2007 to Exchange 2013 and do not want to change any settings on the existing 2007 servers.
I have created new dns entry mailx.abc.com with two IPs of both exchange 2013 and changed the Outlook Anywhere internal URL on both Exchange 2013 server to mailx.abc.com.
So by doing these, I think all existing clients will still connect to exchange 2007 and after moving their mailbox they will be connect to exchange 2013.
In short I am not redirecting or using 2013 as proxy for 2007 clients and clients whose mailbox is on exchange 2013 will directly connect to 2013 server.
Questions are, Is this the right way to migrate all the users to Exchange 2013?
Will it affect the operation of existing Exchange 2007 server?

Read the below blog on Client Connectivity in Exchange co-existence. There can't be better blog than this on this topic.
http://blogs.technet.com/b/exchange/archive/2014/03/12/client-connectivity-in-an-exchange-2013-coexistence-environment.aspx
Clients connect to Exchange from Internal-Outlook, External-Outlook, Web & Active Sync.
For Internal the configuration that you have mentioned should work as clients would get Autodiscover information from Active Directory (SCP) and get connected to right server.
However, for external connectivity it makes sense to use External URL on Exchange 2013 servers (keep the Exchange exposed to Internet), configure legacy URL for exchange 2007 and use Exchange 2013 external URL for mailboxes that are Exchange 2007 and Exchange
2013 for standardization.
Refer article for configuring URLs -
http://silbers.net/blog/2014/01/22/exchange-20072013-coexistence-urls/
- Sarvesh Goel - Enterprise Messaging Administrator

Exchange 2013 - mail hops (Microsoft SMTP Server (TLS))

Hi,
I'm comparing the hops between exchange2013 and exchange2010. I notice Exchange 2013 has an extra hop when sending out emails. Please note that exchange2013 and exchange2010 are not part of the same Active Directory. They are completely separate companies.
The reason why I'm asking about the extra hop is I notice ex2013 first email takes about 1 min to get delivered externally and subsequent email sends are instant. If I haven't emailed for a while (eg. 10mins), the first email takes about 1min to get delivered
again externally and subsequent emails are instant. I don't notice this delay with Exchange 2010.
Exchange 2013 why is there an extra hop (hop #2, Microsoft SMTP Server (TLS))? Could the TLS be the reason of the delay because it is trying to talk to telus smtp via TLS but telus doesn't use TLS and exchange2013 falls back to smtp without TLS for email
send?:
Hop
Delay
from
by
with
time (UTC)
1
ex2013svr.corp.contoso1.com
ex2013svr.corp.contoso1.com
mapi
1/17/2014 5:22:07 PM
2
0 seconds
ex2013svr.corp.contoso1.com
ex2013svr.corp.contoso1.com
Microsoft SMTP Server (TLS)
1/17/2014 5:22:07 PM
3
39 seconds
ex2013svr.corp.contoso1.com 206.x.x.x
cmta1.telus.net
TELUS
1/17/2014 5:22:46 PM
4
1 Second
cmta1.telus.net 209.171.16.74
BAY0-MC2-F44.Bay0.hotmail.com
Microsoft SMTPSVC(6.0.3790.4900)
1/17/2014 5:22:47 PM
Exchange 2010 doesn't have the 'Microsoft SMTP Server (TLS)' hop:
Hop
Delay
from
by
with
time (UTC)
1
ex2010svr.corp.contoso2.com
ex2010svr.corp.contoso2.com
mapi
1/17/2014 5:20:48 PM
2
0 seconds
ex2010svr.corp.contoso2.com 98.x.x.x
skaro.stargate.ca
ESMTP
1/17/2014 5:20:48 PM
3
1 Second
skaro.stargate.ca 98.143.80.200
SNT0-MC2-F53.Snt0.hotmail.com
Microsoft SMTPSVC(6.0.3790.4900)
1/17/2014 5:20:49 PM

Are you using Self Signed Cert? If yes!!!
In Exchange 2013, Setup creates a self-signed certificate. By default, TLS is enabled. This enables any sending system to encrypt the inbound SMTP session to Exchange. By default, Exchange 2013 also attempts TLS for all remote connections.
Cheers,
Gulab Prasad
Technology Consultant
Blog:
http://www.exchangeranger.com    Twitter:
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   Check out CodeTwo’s tools for Exchange admins
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