Cannot send email via ActiveSync when user connect from Internet (Exchange 2010 SP3 RU5)

Hi All. 
This is the first time I encounter this kind of issue, whenever user connect from the internet they cannot send email from their Phone or Windows Mail App, but they can retrieve email 
But when they connect from Internal Network they can send email. I already test ActiveSync from internet using www.testexchangeconnectivity.com and it pass all tests. 
I also check the Firewall and all the necessary ports already opened (we even open all ports) , the default TTL on the firewall 3600 second. 
From what I read ActiveSync use some kind of HTTP POST or in MS terminology "PING" command, but still have no idea what kind of configuration that should be made to the Firewall so it can pass this "PING" command. Because from what I
see in Android Logcat the problem always related to this PING command 
10-07 08:12:38.714 I/Exchange(31971): Interrupt with reason 1
10-07 08:12:38.714 I/Exchange(31971): Ping task ending with status: -1
10-07 08:12:38.904 D/Exchange(31971): created outputstream
10-07 08:12:39.204 W/Exchange(31971): IOException sending mail
10-07 08:12:39.204 E/Exchange(31971): Generic error for operation SendMail: status 200, result -100
10-07 08:12:39.204 W/Exchange(31971): Aborting outbox sync for error -99
10-07 08:12:39.274 I/Exchange(31971): Ping task starting for 3
10-07 08:12:39.304 D/SyncManager(644): failed sync operation [email protected] u0 (com.android.exchange), com.android.email.provider, USER, latestRunTime 71219435, EXPEDITED, reason: 10040, SyncResult: stats [ numIoExceptions: 1]
10-07 08:12:39.304 D/SyncManager(644): not retrying sync operation because SYNC_EXTRAS_DO_NOT_RETRY was specified [email protected]  u0 (com.android.exchange), com.android.email.provider, USER, latestRunTime 71220078, EXPEDITED, reason: 10040

Hi ronaldosy,
How about the work flow of Outlook or OWA on PC internally/externally?
If only phone has this issue, I suggest ask ActiveSync Forum for help so that you can get more professional suggestions. For your convenience:
http://social.technet.microsoft.com/Forums/exchange/en-US/home?forum=exchangesvrmobility
Best Regards,
Allen Wang

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    name 172.23.0.0 LI-NET
    name 172.22.0.0 TX-NET
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    name 12.127.16.69 web-dns-2
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    name 64.208.123.130 TX-PIX
    name 24.38.31.80 CT-PIX
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    network-object 24.38.35.192 255.255.255.248
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    network-object web-dns-2 255.255.255.255
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    static (inside,outside) 24.38.31.69 172.20.8.2 netmask 255.255.255.255 0 0
    static (DMZ,outside) 24.38.31.94 192.168.10.141 netmask 255.255.255.255 0 0
    static (inside,outside) 24.38.31.71 172.20.1.11 dns netmask 255.255.255.255 0 0
    static (DMZ,outside) 24.38.31.93 192.168.10.140 netmask 255.255.255.255 0 0
    static (DMZ,inside) 24.38.31.93 access-list static-dmz-to-ct-1 0 0
    static (DMZ,inside) 24.38.31.94 access-list static-dmz-to-ct-2 0 0
    static (inside,outside) 24.38.31.92 172.20.1.56 netmask 255.255.255.255 0 0
    static (DMZ,outside) 24.38.31.91 192.168.10.138 netmask 255.255.255.255 0 0
    static (DMZ,outside) 24.38.31.90 192.168.10.139 netmask 255.255.255.255 0 0
    static (inside,outside) 24.38.31.72 172.20.1.20 netmask 255.255.255.255 0 0
    static (inside,outside) 24.38.31.73 172.20.1.21 netmask 255.255.255.255 0 0
    static (inside,outside) 24.38.31.70 172.20.1.91 netmask 255.255.255.255 0 0
    static (DMZ,outside) 24.38.31.88 192.168.10.136 netmask 255.255.255.255 0 0
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    aaa-server RADIUS deadtime 10
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    aaa authentication http console LOCAL
    aaa authentication serial console LOCAL
    aaa authentication telnet console LOCAL
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    http 65.51.181.80 255.255.255.248 outside
    http 208.65.108.176 255.255.255.240 outside
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    no snmp-server location
    no snmp-server contact
    snmp-server community m0rroW(0
    no snmp-server enable traps
    floodguard enable
    sysopt connection permit-ipsec
    sysopt connection permit-pptp
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    crypto ipsec transform-set 3des-md5 esp-3des esp-md5-hmac
    crypto dynamic-map dyn_map 20 match address vpn-dyn-match
    crypto dynamic-map dyn_map 20 set transform-set 3des-sha
    crypto map ct-crypto 10 ipsec-isakmp
    crypto map ct-crypto 10 match address vpn-ct-li-gre
    crypto map ct-crypto 10 set peer LI-PIX
    crypto map ct-crypto 10 set transform-set 3des-sha
    crypto map ct-crypto 15 ipsec-isakmp
    crypto map ct-crypto 15 match address vpn-ct-li
    crypto map ct-crypto 15 set peer LI-PIX
    crypto map ct-crypto 15 set transform-set 3des-sha
    crypto map ct-crypto 20 ipsec-isakmp
    crypto map ct-crypto 20 match address vpn-ct-ny
    crypto map ct-crypto 20 set peer NY-PIX
    crypto map ct-crypto 20 set transform-set 3des-sha
    crypto map ct-crypto 30 ipsec-isakmp
    crypto map ct-crypto 30 match address vpn-ct-tx
    crypto map ct-crypto 30 set peer TX-PIX
    crypto map ct-crypto 30 set transform-set 3des-sha
    crypto map ct-crypto 65535 ipsec-isakmp dynamic dyn_map
    crypto map ct-crypto client authentication ct-rad
    crypto map ct-crypto interface outside
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    isakmp key ******** address 216.138.83.138 netmask 255.255.255.255 no-xauth no-c
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    isakmp key ******** address NY-PIX netmask 255.255.255.255 no-xauth no-config-mo
    de
    isakmp key ******** address TX-PIX netmask 255.255.255.255 no-xauth no-config-mo
    de
    isakmp identity address
    isakmp nat-traversal 20
    isakmp policy 10 authentication pre-share
    isakmp policy 10 encryption 3des
    isakmp policy 10 hash sha
    isakmp policy 10 group 2
    isakmp policy 10 lifetime 86400
    isakmp policy 20 authentication pre-share
    isakmp policy 20 encryption 3des
    isakmp policy 20 hash md5
    isakmp policy 20 group 2
    isakmp policy 20 lifetime 86400
    isakmp policy 30 authentication pre-share
    isakmp policy 30 encryption 3des
    isakmp policy 30 hash md5
    isakmp policy 30 group 1
    isakmp policy 30 lifetime 86400
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    vpngroup remotectusers dns-server 172.20.1.5
    vpngroup remotectusers wins-server 172.20.1.5
    vpngroup remotectusers default-domain morrowny.com

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    I think the path of least resistance would be to get a new user account added to the MySQL database that you can access remotely with your Java program. This account can be locked down for read only access and be locked down to the specific IP or IP range that your Java program will be connecting from.
    Again I applaud your creativity but truly this seems like a hack because of the complexity and security concerns you are introducing and I think is a path to the land of trouble. Hopefully you will be able to get a remote account set up.

  • HELP! HELP! Please.... Cannot send email via SMTP....

    Hi,
    Not posted here before but this really is a last ditch attempt to get my email working. I'm at my wits end with this.
    I reported a problem that I could not send mail via SMTP (with Outlook) last December (2014). I kept getting a message from the mail server stating "421 Too many messages". They guys on live chat tried for an hour to get it working, finally gave up and told me to use WebMail instead. Ok, that worked but... in January that went off completely and I found that BT had removed my mailbox from the system!
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    421 is a SERVER message which is telling me that the BT Mail server is not configured for enough connections. Either that or it's severely overloaded. This is BT's problem - not mine but all BT have done is fob me off with excuses for 3 months and now I'm back to square one. the support guys have no idea what this message means.
    Today I was told that if I wanted it sorted I had to pay for BT Expert help.
    What???  I don't need an "expert". I just want them to configure their server properly!
    Can ANYONE - anyone from BT please, please help me to get this sorted. I'm tearing my hair out and as you may have guessed by now I'm also very angry about this.
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    Solved!
    Go to Solution.

    Yes of course I've contacted the Premium Mail help number. I've called them many, many times without any success at all and since I've been calling from abroad it's cost me a fortune to get nowhere.
    These forums are for the BT Community. I'm part of the community since I still have BT services. This isn't a Broadband forum. As I've indicated though, I've been with BT for over 35 years so I think that entitles me to some sort of service - even from here if possible.
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