Multiple Exchange 2013 SSL Certificates & Web Services URLs

I have two Exchange 2013 CU5 Standard servers in a DAG.  Both servers have both the CAS and Mailboxes roles installed.  
The servers are running Server 2012 Standard.  The DAG uses a file share witness server.  
The witness server and one Exchange server, which is usually the active server, are on the same subnet in our primary data centre. 
The second Exchange server is on a different subnet in our backup data centre across town.
The domain that these servers are in is part of a forest with another domain. 
That domain is, physically, in another jurisdiction.  The domains share a namespace. 
All users in both domains have username at name.com as their e-mail address.
The other domain has two Exchange 2013 servers in a DAG.  It also has one Exchange 2007 server, that is being phased out. 
All messages that my domain users send to external recipients pass though the Exchange servers in my domain, a firewall for my domain, an Internet connection, a firewall in the other domain, the Exchange servers in the other domain, the firewall for
the other domain, and then out to the external recipients.  The reverse path is followed for inbound mail from external senders. 
All ActiveSync traffic for my users passes through the Exchange servers and a proxy server in the other domain. 
I have a self-signed SAN certificate on the Exchange servers in my domain. 
That certificate is also deployed on all of the mobile devices that my users have.
I have been asked to see if I can set things up so that a test user can send and receive e-mail with their mobile device, and have that traffic go from my Exchange servers, through the firewall for my domain, and out to external recipients. 
Due to a lack of test systems, I have been asked to develop this on my production servers, without disrupting the existing mail flow. 
Is that possible?  What would need to be done to accomplish this? 
If the test is possible, and successful, my Exchange servers, and all other relevant systems, would be changed so that all mail traffic from my domain no longer goes through the other domain.

You could set a test send connector for @outsidedomain.com to use your Exchange servers as source servers, and make sure you have at least one reverse DNS entry (PTR) in place for whatever IP your external firewall presents to the world for the Exchange
servers. This is critical in order not to have the rest of the world discard your emails (spammers usually fail the reverse DNS name).
For incoming traffic, you could use a DNS domain that you own and that's not in use currently (eg oldcompany.com belonging to someone your current employer purchased) and have an MX record for this pointing to the public IP address(es) of the published Exchange
servers.
However mail routing cannot be done to work one way with mobile devices and another way with Outlook. In this case both ActiveSync and Outlook are simply interfaces to send/receive emails using your common SMTP infrastructure. So once configured for the
test as above, both ActiveSync, Outlook, OWA, EWS clients will send/receive emails in the same way. In the example above - anyone sending to @outsidedomain.com, regardless it's the users hosted on your Exchange servers or the ones in the other domain, will
be sent using the new route.

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    3.dlh☻E6465040334343305252F4365727450726F762F4365727450726F766973696F6E696E67536
    572766963652E737663] (010C4D532D55432D436C69656E7402056874747073030F6C796E633230
    31332E646C6802453634363530343033333433343333303532353246343336353732373435303732
    36463736324634333635373237343530373236463736363937333639364636453639364536373533
    36353732373636393633363532453733373636335D)
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    Sender:57.20.120.85:67, Size:408
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    3.dlh☻E6465040334343305252F4365727450726F762F4365727450726F766973696F6E696E67536
    572766963652E737663] (010C4D532D55432D436C69656E7402056874747073030F6C796E633230
    31332E646C6802453634363530343033333433343333303532353246343336353732373435303732
    36463736324634333635373237343530373236463736363937333639364636453639364536373533
    36353732373636393633363532453733373636335D)
        DHCP: End of this option field
    --End Packet--
    Received Packet
    Sender:57.20.120.100:67, Size:408
    --Begin Packet--
    DHCP: ACK                (xid=5C1E8177)
    DHCP: Op Code           (op)      = 1
    DHCP: Hardware Type     (htype)   = 6
    DHCP: Hops              (hops)    = 0
    DHCP: Transaction ID    (xid)     = 1545503095
    DHCP: Seconds           (secs)    = 0
    DHCP: Flags             (flags)   = 0000
    DHCP: Client IP Address (ciaddr)  = 57.56.69.138
    DHCP: Your IP Address   (yiaddr)  = 0.0.0.0
    DHCP: Server IP Address (siaddr)  = 0.0.0.0
    DHCP: Relay IP Address  (giaddr)  = 0.0.0.0
    DHCP: Client HW Address (chaddr)  = E0DB55DE8993
    DHCP: Server Host Name  (sname)   =
    DHCP: Boot File Name    (file)    =
    DHCP: Magic Cookie                = 99.130.83.99
    DHCP: Option Field
        DHCP: DHCP MESSAGE TYPE(  53) = (Length: 1) DHCP ACK
        DHCP: Server Identifier(  54) = (Length: 4) 57.20.120.100
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        DHCP: SIP Server( 120)        = (Length: 18) enc:0 lync2013.dlh.de (00086C79
    6E633230313303646C6802646500)
        DHCP: Host Name(  12)         = (Length: 0)
        DHCP: Vendor Identifier(  60) = (Length: 0)
        DHCP: Param Req List(  55)    = (Length: 0) 0 0
        DHCP: Vendor Info(  43)       = (Length: 130) ☺♀MS-UC-Client☻♣https♥☼lync201
    3.dlh☻E6465040334343305252F4365727450726F762F4365727450726F766973696F6E696E67536
    572766963652E737663] (010C4D532D55432D436C69656E7402056874747073030F6C796E633230
    31332E646C6802453634363530343033333433343333303532353246343336353732373435303732
    36463736324634333635373237343530373236463736363937333639364636453639364536373533
    36353732373636393633363532453733373636335D)
        DHCP: End of this option field
    --End Packet--
    Received Packet
    Sender:57.20.120.100:67, Size:408
    --Begin Packet--
    DHCP: ACK                (xid=5C1E8177)
    DHCP: Op Code           (op)      = 1
    DHCP: Hardware Type     (htype)   = 6
    DHCP: Hops              (hops)    = 0
    DHCP: Transaction ID    (xid)     = 1545503095
    DHCP: Seconds           (secs)    = 0
    DHCP: Flags             (flags)   = 0000
    DHCP: Client IP Address (ciaddr)  = 57.56.69.138
    DHCP: Your IP Address   (yiaddr)  = 0.0.0.0
    DHCP: Server IP Address (siaddr)  = 0.0.0.0
    DHCP: Relay IP Address  (giaddr)  = 57.56.69.131
    DHCP: Client HW Address (chaddr)  = E0DB55DE8993
    DHCP: Server Host Name  (sname)   =
    DHCP: Boot File Name    (file)    =
    DHCP: Magic Cookie                = 99.130.83.99
    DHCP: Option Field
        DHCP: DHCP MESSAGE TYPE(  53) = (Length: 1) DHCP ACK
        DHCP: Server Identifier(  54) = (Length: 4) 57.20.120.100
        DHCP: Client Identifier(  61) = (Length: 0)  ()
        DHCP: SIP Server( 120)        = (Length: 18) enc:0 lync2013.dlh.de (00086C79
    6E633230313303646C6802646500)
        DHCP: Host Name(  12)         = (Length: 0)
        DHCP: Vendor Identifier(  60) = (Length: 0)
        DHCP: Param Req List(  55)    = (Length: 0) 0 0
        DHCP: Vendor Info(  43)       = (Length: 130) ☺♀MS-UC-Client☻♣https♥☼lync201
    3.dlh☻E6465040334343305252F4365727450726F762F4365727450726F766973696F6E696E67536
    572766963652E737663] (010C4D532D55432D436C69656E7402056874747073030F6C796E633230
    31332E646C6802453634363530343033333433343333303532353246343336353732373435303732
    36463736324634333635373237343530373236463736363937333639364636453639364536373533
    36353732373636393633363532453733373636335D)
        DHCP: End of this option field
    --End Packet--
    Received Packet
    Sender:57.20.120.100:67, Size:408
    --Begin Packet--
    DHCP: ACK                (xid=5C1E8177)
    DHCP: Op Code           (op)      = 1
    DHCP: Hardware Type     (htype)   = 6
    DHCP: Hops              (hops)    = 0
    DHCP: Transaction ID    (xid)     = 1545503095
    DHCP: Seconds           (secs)    = 0
    DHCP: Flags             (flags)   = 0000
    DHCP: Client IP Address (ciaddr)  = 57.56.69.138
    DHCP: Your IP Address   (yiaddr)  = 0.0.0.0
    DHCP: Server IP Address (siaddr)  = 0.0.0.0
    DHCP: Relay IP Address  (giaddr)  = 57.56.69.130
    DHCP: Client HW Address (chaddr)  = E0DB55DE8993
    DHCP: Server Host Name  (sname)   =
    DHCP: Boot File Name    (file)    =
    DHCP: Magic Cookie                = 99.130.83.99
    DHCP: Option Field
        DHCP: DHCP MESSAGE TYPE(  53) = (Length: 1) DHCP ACK
        DHCP: Server Identifier(  54) = (Length: 4) 57.20.120.100
        DHCP: Client Identifier(  61) = (Length: 0)  ()
        DHCP: SIP Server( 120)        = (Length: 18) enc:0 lync2013.dlh.de (00086C79
    6E633230313303646C6802646500)
        DHCP: Host Name(  12)         = (Length: 0)
        DHCP: Vendor Identifier(  60) = (Length: 0)
        DHCP: Param Req List(  55)    = (Length: 0) 0 0
        DHCP: Vendor Info(  43)       = (Length: 130) ☺♀MS-UC-Client☻♣https♥☼lync201
    3.dlh☻E6465040334343305252F4365727450726F762F4365727450726F766973696F6E696E67536
    572766963652E737663] (010C4D532D55432D436C69656E7402056874747073030F6C796E633230
    31332E646C6802453634363530343033333433343333303532353246343336353732373435303732
    36463736324634333635373237343530373236463736363937333639364636453639364536373533
    36353732373636393633363532453733373636335D)
        DHCP: End of this option field
    --End Packet--
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