Can't send mail when connected to vpn

I'm hooked up with a private vpn service using OpenVpn. Everything works beautifully -- except that I can't send mail (receiving is no problem) because the SMTP ports offered through Mail 4.5 (ports 25, 465, 587) are blocked by many VPN providers as an anti-spam measure. I can't use port 993 with SSL because I live in Monaco, which has one ISP -- and it does not provide or support secure email (which is one of the reasons I want the VPN).
Is there another port I can select for SMTP, or some configuration tricks I'm missing? Thanks...:)

Hello Brian,
Basically this is the VPN group:
crypto isakmp client configuration group open
key (something)
dns 192.168.1.1 8.8.8.8
domain something.com
pool SDM_POOL_1
save-password
backup-gateway 192.168.1.1
max-users 5
netmask 255.255.255.0
banner ^Cyou have connected to the vpn-ings!. well done! ^
I see that you are doing tunnel all, and you are not split tunneling on this configuration, what you can do is to use split tunnel, under this configuration as follow:
ip access-list extended SPLIT_TUNNEL
permit ip XXXXX XXXXX 192.168.1.0 0.0.0.255
XXXXX --> are the inside subnets
Then under this:
crypto isakmp client configuration group open
acl SPLIT_TUNNEL
This will allow you to have access to the internal subnets through the tunnel and have access to internet through the internet connection on your computer.
For further details take a look to this document:
- http://www.cisco.com/c/en/us/support/docs/routers/3600-series-multiservice-platforms/91193-rtr-ipsec-internet-connect.html
Don't use Any on your ACL statements for split tunneling purposes.
Let me know how it works out!
Please don't forget to rate and mark as correct the helpful Post!
David Castro,
Regards,

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Can't send mail when using mobile broadband

Hi
I am getting quite frustrated as I can't send mail when using my mobile broadband modem! I can receive mail, and surf the internet etc, but mail just wont send!(i get the usual cannot send try later/resend options). I thought this might be an issue with my mobile broadband but have recently reinstalled it. When at home on a wireless network I have no such issues.
Any help appreciated
Charlie

Cgienke wrote:
I am not using a SMTP it is a Pop3 domain name account from freeparking and uses mail.'NAME'.com for incoming and outgoing mail!
Even though your e-mail service uses the same URL for POP3 and SMTP servers, in the software sense you actually do have separate POP3 and SMTP servers, although they may be hosted on the same machine, or the requests are routed via some "smoke and mirrors" to the right host.
It is not related to my ISP at home, which is Virgin media. My mobile broadband provider is 3. I was thinking it might be that I need to change the port settings in mail when using my mobile modem, but don't know what to change them too(or how to do it!) or configure the modem differently but again not sure what to do there!
Check with the freeparking online help to see if it supports port 587 or some such.
Also try Mail's "Connection Doctor" (under the Window menu) when you're away from home to see if that shows anything useful.
Since you can send e-mail from that SMTP server when you're at home but not when you're using your mobile broadband, I think one of two possibilities is likely: (a) Your mobile broadband provider is blocking your attempts to access the freeparking SMTP server and/or port. (b) The freeparking SMPT server for some reason doesn't like being communicated with via your mobile broadband provider. I'd check with each of them to explore these options.
Does your mobile broadband provider have an SMTP server that you can use instead of the freeparking one?
My modem(Huawei E220) is not particularly Mac friendly as it is, and I believe Mail can be quite sensitive when servers don't respond immediately?
Yes. Mail seems to have a fixed time-out value for server responses.

I can not send mail when at school. Please help

I can not send mail when at school. Please help

What is the email provider? If it is from your home Internet service provider, they usually block sending when not on their network. If this is the case, see if you can log into the smtp server with username and password. If they allow that, you can enter that in the email account settings.

Can't Browse Web when connected to VPN

Hi,
I got interested in networks about a year ago. We had some spare networking kit lying around in our office and I decided to set up a lab.
I've been able to configure NAT w/ PAT on a cisco 3825.
I've got 1 access list, "Overloading" my OUTSIDE int, and a few "ip nat inside source static..." entries to handle my port forwards.
It's a very basic setup.
The router died recently, so I got a cheap replacement form ebay. Setting it all up was WAY easier than last time, so I decided to try something new.... VPN.
I'd previously had a port forward to a computer that was a VPN server, but I was able to use Cisco CCP to help me configure VPN. Yes, technically cheating for all you CLI-heads out there, so sorry-- to make you happy, I did thoroughly inspect and spent extra time appreciating the code it wanted to inject to my router.
Now, I've got VPN working, and I can access all the PC's on the LAN I'm VPN'ing to, but -- I can't access the web when connected to VPN.
I've fiddled with the access list, trying to make it ANY/ANY.
I'm not really sure what to do.
I looked around and most of the stuff out there is for a site-to-site, or PAT running on a tunnel...
My issue is pretty basic, probably. I just cant access outside when on VPN.
I'm more than willing to have another translation method.
I've attached my router config.
Can you have a look and let me know what would need changing...
Really appreciate any insight.
Thanks,
Brian

Hello Brian,
Basically this is the VPN group:
crypto isakmp client configuration group open
key (something)
dns 192.168.1.1 8.8.8.8
domain something.com
pool SDM_POOL_1
save-password
backup-gateway 192.168.1.1
max-users 5
netmask 255.255.255.0
banner ^Cyou have connected to the vpn-ings!. well done! ^
I see that you are doing tunnel all, and you are not split tunneling on this configuration, what you can do is to use split tunnel, under this configuration as follow:
ip access-list extended SPLIT_TUNNEL
permit ip XXXXX XXXXX 192.168.1.0 0.0.0.255
XXXXX --> are the inside subnets
Then under this:
crypto isakmp client configuration group open
acl SPLIT_TUNNEL
This will allow you to have access to the internal subnets through the tunnel and have access to internet through the internet connection on your computer.
For further details take a look to this document:
- http://www.cisco.com/c/en/us/support/docs/routers/3600-series-multiservice-platforms/91193-rtr-ipsec-internet-connect.html
Don't use Any on your ACL statements for split tunneling purposes.
Let me know how it works out!
Please don't forget to rate and mark as correct the helpful Post!
David Castro,
Regards,

Can't send mail when away from home

10.5.2
I can't get my MacBook Pro to send email when I'm away from home but the connection doctor says it is connected to all of the smtp servers in my mail accounts.
Any help will be greatly appreciated.

Most, if not all ISPs, block the use of SMTP servers that are outside of their network (or not provided by the ISP being used for your internet connection) on Port 25. Some ISPs allow the use of an authenticated SMTP server only that is outside of their network, but some block all available ports that can be used with an SMTP server that is outside of their network.
These restrictions are in place as part of an overall effort to prevent spam emanating from the ISP's domain.
Earthlink has an authenticated SMTP server, as does a .Mac account, so you should be able to send messages with your Earthlink and .Mac accounts when connected to different ISPs. If not and you are using 25 for the SMTP server port for these SMTP servers, try using 587 for the SMTP server port instead for each.
You can only use the .Mac authenticated SMTP server to send messages with a .Mac account, but it should be possible to use Earthlink's authenticated SMTP server to send messages with any account.
If the ISP you are using for your internet connection is very restrictive in this regard, there isn't much you can do except for contacting the ISP being used for their requirement when using an SMTP server that is outside of their network, or send via webmail access for the account using a browser.

Can't send mail but connection doctor says server is ok

I changed my MS Exchange username from [email protected] to [email protected] but my email address remains [email protected] So I changed my account settings (I have the exchange account set up as IMAP. I can receive messages but I cannot send. I have checked the settings a thousand times, they are correct. The funny thing is the connection doctor says my outgoing mail server connection is good "Connection and login to server succeeded", but when I try to send send a mail I get "Unable to send mail, check x y z" I don't remember the error exactly because now the send button is just grayed out when I try to send from that account.

I installed Eudora and imported my mail settings from Apple Mail. I did NO entry of the server settings, it came directly from Apple Mail. I can send from Eudora but I cannot send from Apple Mail. Go figure.

Can't send mail when in wi-fi mode

I let my iPhone switch to wi-fi when I'm home because I only get Edge in the location of my house. How come when I try to send an email while in wi-fi mode, the "sending" progress bar just sits there for a while before returning an error saying that it couldn't send? I have to turn wi-fi off and let it use edge in order for the mail to go out. I'm using optonline.net as my mail server and someone at optonline explained to me how to get it to work on wi-fi back when I got my iPhone, but I have since forgotten. The mail settings for this account are as follows:
*_Incoming Mail Serve_r*
*Host Name*: mail.optonline.net
*_Outgoing Mail Server_*
SMTP
Primary Server: cwmx.com
*Ohter SMTP Servers*
mail.optonline.net (On)
cwmx.com (On)
AT&T SMTP Server (Off)
Advanced
Use SSL: OFF
Authentication: password
Server Port: 110
Thanks in advance guys.

My Last Confession wrote:
I think I figured this out. When I'm on wi-fi, I have to switch to using mail.optonline.net. But when using Edge or 3G, I have to switch to cwmx.com For some reason when on wi-fi cwmx.com doesn't work.
For some GOOD reason. If it did work when not on AT&T's network every spammer in the world would use it, because it doesn't require authentication.
You would think that setting the primary outgoing to mail.optonline.net and the secondary to cwmx.com would fix this, but it doesn't; I still have to manually turn off cwmx.com if I want to send successful emails from the iphone over wi-fi
This works for me, so something else is going on here. Have you entered your user id and password for optonline server correctly?

I can´t send mails- the connection to my server "times out"

The app. tries to connect to the server but keeps on timing out. i have tried 2 servers to no avail

https://support.mozilla.org/en-US/kb/cannot-send-messages

Mail can't send mail on home network

I am trying to help a friend who wants to move from Entourage to Mail. He has a MacBook Pro with 10.6.4 installed and his company uses Exchange 2003. He is moving to Mail due to serious calendar and contact syncing issues through Entourage and his iPhone/iCal/Address Book.
I have setup his Mail account to use IMAP with the Exchange Server. He can receive mail this way, but he cannot send it. Actually he can only send mail when he is at work on his company's network. I have turned off SSL and authentication is through Username and Password.
Funny thing is that Entourage can send and receive mail anywhere he has a connection, but Mail cannot. His company's IT department says that the settings I have in place should work.
How can I further troubleshoot this problem? Is it a server problem? I know 10.6's Mail doesn't support Exchange 2003, but I am not looking for full integration of exchange services.

You may be SOL as you need an SMTP server to send mail and the IT folks may not have it set up. You need a proper SMTP relay to send the mail, period. It doesn't matter what it's called, though convention usually has it set to smtp.example.com. mail.example.com would more often be the address for IMAP or POP connections.
Regarding the inability to send mail from an external network, this is the same problem: You still need an SMTP server to send emails. It's just that the SMTP server on the external network is likely different than the corporate SMTP server. What external network is it, and what is the SMTP server they have set up for machines within their network? Note that many networks don't enable outbound SMTP for random clients due to SPAM reasons.

I've set up email on my iPad (talk mails when connected to my home router and ISP. When connected to a router at another location with a different ISP I can receive mail but not send it. Is there any way round this

I've set up email on my iPad (talktalk.net) and can send and receive mails when connected to my home router and ISP. When connected to a router at another location with a different ISP I can receive mail but not send it. Is there any way round this?

I've set up email on my iPad (talktalk.net) and can send and receive mails when connected to my home router and ISP. When connected to a router at another location with a different ISP I can receive mail but not send it. Is there any way round this?

Mail only sends messages when connected to WiFi? Hmmmm.

Hi. I've got a POP3 email account that I have to set up manually. For some reason, emails can only be sent when connected to WiFi but not over a cellular data network. Anyone got any ideas? I can receive mail fine through either WiFi or Cellular Data Network.
Many thanks,
Max

Do you have a wireless network at home and Is the email account provided by your internet service provider associated with your wireless network?
Most, if not all internet service providers block the use of SMTP servers that are outside of their network or not provided by the ISP being used for your internet connection at the time unless the SMTP server is authenticated. The same applies when connected to the internet via the cellular network. Recieving is not a problem regardless the ISP being used for your internet connection at the time.
If the email account is provided by your ISP, most ISPs do not have an authenticated SMTP sever for the email account they provide.
Both my email accounts have an authenticated SMTP server and I've never had a problem sending with either account regardless the ISP associated with a wi-fi network I'm connected to at the time or when connected to AT&T's cellular network - for 2+ years aporoaching 3 years this July.

Can't access non-VPN resources when connected to VPN

I need to access web based resources over a VPN for work. My admin gave me the connection parameters, and I can connect to the VPN and access what I need, no problem. But when connected to VPN, I can't access websites, Subversion repositories, Skype, etc. that are not on the VPN.
On Windows, there's a connection property on VPN connections called "Use default gateway". With that option cleared on my Windows machine, I can access both VPN and non-VPN resources simultaneously. I can't spot anything equivalent in the VPN connection in Network Preferences.
So I guess the question is: what network settings on Mac (Snow Leopard) will enable me to access both VPN and normal resources simultaneously?

I have found a workaround. It isn't optimal, and it's disappointing that VPN is so poorly supported on Mac. Though the specific IPs are probably applicable only to the particular VPN I connect to, maybe the general idea can be of help to others and your network admins can supply the particular IPs you need.
1. My Admin had me open Network Preferences, select the VPN connection, click the Tools icon at the bottom, and select Set Service Order. In that dialog, move the VPN connection to the bottom of the list (my EVDO modem that gets me my internet connection is fist in the list). Apply this change.
2. Next, my admin asked me to run the following in Terminal, once when VPN was not connected (but internet was connected), and again with VPN connected, and send him the output:
*netstat -nr*
3. After looking at the terminal output, admin told me to run the following in Terminal with the VPN connected:
*sudo route add -net 10.123 -netmask 255.255.0.0 10.123.50.1*
After disconnecting both VPN and Internet connection and reactivating each in turn (internet, then VPN), I was able to access both VPN and non-VPN resources simultaneously.
The bad news is that every time I need to connect I have to run route add in Terminal and enter my password. I will probably make a shell script to at least run the command so I don't have to remember it.
Here's hoping this helps if others bump into this pernicious little problem.

TS1702 cannot send Mail   The connection to the outgoing server failed. Additional Outgoing Mail Servers can be configured in Settings Mail, COntacts, Calendars

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See here for troubleshooting the SMTP settings (outgoing mail server on your carrier's servers)
http://www.apple.com/uk/support/iphone/mail/
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Cant send emails from gmail or yahoo when connected to vpn

I use a vpn to mask my IP address. When I am connected through my VPN I cannot send emails from my gmail or yahoo accounts through thunderbird
If i disconect vpn they go through fine

Just a guess, but if you change the outgoing server name to an IP address such as 74.125.136.108 for Gmail, does it work?
https://support.hidemyass.com/entries/24893686-SMTP-Sending-emails-while-connected-to-VPN#thunderbird

Users can only connect to RD farm website and cannot remote into terminal server , when connected via VPN

Hello,
I have a RD farm using 3 Win 2012 servers (1 broker and 2 session host), for internal use only, have not
configured gateway for internet access.
Users are able to connect to RD farm website and remote into terminal server, within office
but can only connect to RD farm website and cannot remote into terminal server , when connected via VPN
Its takes long time at securing connection and fails.
Thanks

Hi,
Thank you for your posting in Windows Server Forum.
First of all I would suggest you to configure RD gateway role on your server and pass all the connection through it because it’s a best practice to use RD Gateway in RDS Farm.
Apart from this, if you are not using RD Gateway then you must check that you have successfully forwarded port 3389 for RDS to access via VPN. Also check that you have made configuration under IIS Manager to enable Forms Authentication. Please check
this link.
In addition, please refer beneath article for additional details.
1. How to Access Windows Remote Desktop Over the Internet
2. Remote Desktop Services in Windows 2008 R2 – Part 3 – RD Web Access & RemoteApp
(For reference)
Hope it helps!
Thanks,
Dharmesh

Can't send mail when connected to vpn

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