ASA Configuration Woes

USMCGrunt

2[H]4U
Joined
Mar 19, 2010
Messages
3,103
This is basically a copy and paste from the Cisco forums, hopefully another group of eyes can help me here.

Issue 1:
I have an internal Spiceworks webserver sitting behind a 5512. I can't seem to figure out how to configure hairpin NAT using ASDM. I'm not familiar enough with the CLI anymore to tackle it that way. Additionally, initial requests are made on port 80 and then changed by the webserver to port 9675. The webserver is on a domain controller that sits on the same network and utilizes the same interface as the rest of the LAN subnet.

Issue 2:
External users are able to access the webserver and use it but files do not load. I have a page with JPGs that do not load and every link to PDF files does not load. They worked just fine prior to adding the ASA so I'm assuming the ASA is filtering it out somehow but I'm not sure where.

Issue 3:
Internal traffic is being filtered oddly. Prior to adding the ASA, users on the same network as the domain controllers had drive maps applied to them through group policies. Since adding the ASA, those drive mappings are no longer being done.

e0/0: Outside interface - Public IP --->ISP Fiber switch
e0/5: Inside interface - LAN Network --> LAN Switch --->Domain Controllers & user workstations.

Bonus Problem:
I have a /28 network provided by my ISP. Internally, we have a phone system and two data networks that I'd like to distribute our public IPs to. Unfortunately, I see that it's not as simple as assigning an individual public IP to each hardware interface. So here's what I'd like to do....how do I do it:

e 0/0 - Public IP 71.0.0.1/28 physical connection to ISP
e 0/1 - Public IP 71.0.0.2/28 physical connection to Internal Phone System
e 0/2 - Public IP 71.0.0.3/28 physical connection to LAN2 (192.168.0.0/24)
e 0/5 - Internal LAN1 10.0.0.0/24 physical connection to LAN1 switches
 
Update:
I've reconfigured our internal DNS to house the zone for our public listings and instead of resolving to the public IP for the webserver's URL it resolves to the internal IP (Temporary, would still prefer to have hairpin NAT configured). In this manner, internal hosts are able to see the JPEGs and load the PDF files. This further verifies that the ASA is filtering those files.
 
Current Config:

: Saved
:
: Serial Number: FCH200678GP
: Hardware: ASA5512, 4096 MB RAM, CPU Clarkdale 2792 MHz, 1 CPU (2 cores)
:
ASA Version 9.2(2)4
!
hostname
domain-name
enable password
names
!
interface GigabitEthernet0/0
nameif Inside
security-level 100
ip address 10.0.5.1 255.255.255.0
!
interface GigabitEthernet0/1
shutdown
no nameif
no security-level
no ip address
!
interface GigabitEthernet0/2
shutdown
no nameif
no security-level
no ip address
!
interface GigabitEthernet0/3
shutdown
no nameif
no security-level
no ip address
!
interface GigabitEthernet0/4
shutdown
no nameif
no security-level
no ip address
!
interface GigabitEthernet0/5
nameif Outside
security-level 0
ip address 71.14.0.1 255.255.255.240
!
interface Management0/0
management-only
nameif management
security-level 100
ip address 192.168.1.1 255.255.255.0
!
ftp mode passive
clock timezone CST -6
clock summer-time CDT recurring
dns server-group DefaultDNS
domain-name lbdnh.local
same-security-traffic permit inter-interface
same-security-traffic permit intra-interface
object network CONT
subnet 10.0.1.0 255.255.255.0
object network FAM
subnet 10.0.2.0 255.255.255.0
object network MAR
subnet 10.0.3.0 255.255.255.0
object network SRV1-->Spiceworks
host 10.0.5.5
object network FS1
host 10.0.5.3
description File Server
object network Computer
host 10.0.5.40
object network NETWORK_OBJ_10.0.4.0_24
subnet 10.0.4.0 255.255.255.0
object network NETWORK_OBJ_10.0.5.0_24
subnet 10.0.5.0 255.255.255.0
object network NETWORK_OBJ_10.0.2.0_24
subnet 10.0.2.0 255.255.255.0
object network NETWORK_OBJ_10.0.3.0_24
subnet 10.0.3.0 255.255.255.0
object service Computer
service tcp source eq 00 destination eq 3389
object network SpiceworksHTTP
host 10.0.5.5
object network SRV1
host 10.0.5.5
object network PublicIP
host 71.14.0.1
object-group service IT
service-object object Computer
object-group protocol TCPUDP
protocol-object udp
protocol-object tcp
object-group service rdp tcp-udp
port-object eq 3389
object-group network DM_INLINE_NETWORK_2
network-object object SRV1-->Spiceworks
network-object object SpiceworksHTTP
object-group network DM_INLINE_NETWORK_1
network-object object NETWORK_OBJ_10.0.2.0_24
network-object object NETWORK_OBJ_10.0.3.0_24
network-object object NETWORK_OBJ_10.0.4.0_24
network-object object NETWORK_OBJ_10.0.5.0_24
access-list Inside_access_in extended deny tcp 10.0.5.0 255.255.255.0 any eq smtp log critical
access-list Inside_access_in extended permit ip any any
access-list Outside_access_in extended deny tcp any 10.0.5.0 255.255.255.0 eq smtp log critical
access-list Outside_access_in extended permit object-group TCPUDP any object Computer object-group rdp
access-list Outside_access_in extended permit object-group TCPUDP any object SRV1 object-group rdp
access-list Outside_access_in extended permit ip any object-group DM_INLINE_NETWORK_2
access-list Outside_cryptomap extended permit ip 10.0.5.0 255.255.255.0 10.0.4.0 255.255.255.0
access-list Outside_cryptomap_1 extended permit ip 10.0.5.0 255.255.255.0 10.0.2.0 255.255.255.0
access-list Outside_cryptomap_2 extended permit ip 10.0.5.0 255.255.255.0 10.0.3.0 255.255.255.0
access-list global_access extended permit icmp any any
access-list global_access extended permit ip object-group DM_INLINE_NETWORK_1 10.0.5.0 255.255.255.0 log
access-list global_mpc extended permit ip interface Outside interface Inside
pager lines 24
logging enable
logging asdm warnings
mtu Inside 1500
mtu Outside 1500
mtu management 1500
no failover
icmp unreachable rate-limit 1 burst-size 1
icmp permit 10.0.5.0 255.255.255.0 Inside
icmp permit 192.168.1.0 255.255.255.0 management
asdm history enable
arp timeout 14400
no arp permit-nonconnected
nat (Inside,Outside) source static NETWORK_OBJ_10.0.5.0_24 NETWORK_OBJ_10.0.5.0_24 destination static NETWORK_OBJ_10.0.4.0_24 NETWORK_OBJ_10.0.4.0_24 no-proxy-arp route-lookup
nat (Inside,Outside) source static NETWORK_OBJ_10.0.5.0_24 NETWORK_OBJ_10.0.5.0_24 destination static NETWORK_OBJ_10.0.2.0_24 NETWORK_OBJ_10.0.2.0_24 no-proxy-arp route-lookup
nat (Inside,Outside) source static NETWORK_OBJ_10.0.5.0_24 NETWORK_OBJ_10.0.5.0_24 destination static NETWORK_OBJ_10.0.3.0_24 NETWORK_OBJ_10.0.3.0_24 no-proxy-arp route-lookup
nat (Inside,Inside) source static NETWORK_OBJ_10.0.5.0_24 NETWORK_OBJ_10.0.5.0_24 destination static PublicIP PublicIP no-proxy-arp
!
object network SRV1-->Spiceworks
nat (Inside,Outside) static interface service tcp 9675 www
object network Computer
nat (Inside,Outside) static interface service tcp 3389 00
object network SpiceworksHTTP
nat (Inside,Outside) static interface service tcp 9675 9675
object network SRV1
nat (Inside,Outside) static interface service tcp 3389 0000
!
nat (Inside,Outside) after-auto source dynamic any interface
access-group Inside_access_in in interface Inside
access-group Outside_access_in in interface Outside
access-group global_access global
route Outside 0.0.0.0 0.0.0.0 71.14.0.1 1
timeout xlate 3:00:00
timeout pat-xlate 0:00:30
timeout conn 1:00:00 half-closed 0:10:00 udp 0:02:00 icmp 0:00:02
timeout sunrpc 0:10:00 h323 0:05:00 h225 1:00:00 mgcp 0:05:00 mgcp-pat 0:05:00
timeout sip 0:30:00 sip_media 0:02:00 sip-invite 0:03:00 sip-disconnect 0:02:00
timeout sip-provisional-media 0:02:00 uauth 0:05:00 absolute
timeout tcp-proxy-reassembly 0:01:00
timeout floating-conn 0:00:00
dynamic-access-policy-record DfltAccessPolicy
user-identity default-domain LOCAL
http server enable
http 192.168.1.0 255.255.255.0 management
http 10.0.5.0 255.255.255.0 Inside
http redirect management 80
no snmp-server location
no snmp-server contact
crypto ipsec ikev1 transform-set ESP-AES-128-SHA esp-aes esp-sha-hmac
crypto ipsec ikev1 transform-set ESP-AES-128-MD5 esp-aes esp-md5-hmac
crypto ipsec ikev1 transform-set ESP-AES-192-SHA esp-aes-192 esp-sha-hmac
crypto ipsec ikev1 transform-set ESP-AES-192-MD5 esp-aes-192 esp-md5-hmac
crypto ipsec ikev1 transform-set ESP-AES-256-SHA esp-aes-256 esp-sha-hmac
crypto ipsec ikev1 transform-set ESP-AES-256-MD5 esp-aes-256 esp-md5-hmac
crypto ipsec ikev1 transform-set ESP-AES-128-SHA-TRANS esp-aes esp-sha-hmac
crypto ipsec ikev1 transform-set ESP-AES-128-SHA-TRANS mode transport
crypto ipsec ikev1 transform-set ESP-AES-128-MD5-TRANS esp-aes esp-md5-hmac
crypto ipsec ikev1 transform-set ESP-AES-128-MD5-TRANS mode transport
crypto ipsec ikev1 transform-set ESP-AES-192-SHA-TRANS esp-aes-192 esp-sha-hmac
crypto ipsec ikev1 transform-set ESP-AES-192-SHA-TRANS mode transport
crypto ipsec ikev1 transform-set ESP-AES-192-MD5-TRANS esp-aes-192 esp-md5-hmac
crypto ipsec ikev1 transform-set ESP-AES-192-MD5-TRANS mode transport
crypto ipsec ikev1 transform-set ESP-AES-256-SHA-TRANS esp-aes-256 esp-sha-hmac
crypto ipsec ikev1 transform-set ESP-AES-256-SHA-TRANS mode transport
crypto ipsec ikev1 transform-set ESP-AES-256-MD5-TRANS esp-aes-256 esp-md5-hmac
crypto ipsec ikev1 transform-set ESP-AES-256-MD5-TRANS mode transport
crypto ipsec ikev1 transform-set ESP-3DES-SHA esp-3des esp-sha-hmac
crypto ipsec ikev1 transform-set ESP-3DES-MD5 esp-3des esp-md5-hmac
crypto ipsec ikev1 transform-set ESP-3DES-SHA-TRANS esp-3des esp-sha-hmac
crypto ipsec ikev1 transform-set ESP-3DES-SHA-TRANS mode transport
crypto ipsec ikev1 transform-set ESP-3DES-MD5-TRANS esp-3des esp-md5-hmac
crypto ipsec ikev1 transform-set ESP-3DES-MD5-TRANS mode transport
crypto ipsec ikev1 transform-set ESP-DES-SHA esp-des esp-sha-hmac
crypto ipsec ikev1 transform-set ESP-DES-MD5 esp-des esp-md5-hmac
crypto ipsec ikev1 transform-set ESP-DES-SHA-TRANS esp-des esp-sha-hmac
crypto ipsec ikev1 transform-set ESP-DES-SHA-TRANS mode transport
crypto ipsec ikev1 transform-set ESP-DES-MD5-TRANS esp-des esp-md5-hmac
crypto ipsec ikev1 transform-set ESP-DES-MD5-TRANS mode transport
crypto ipsec ikev2 ipsec-proposal AES256
protocol esp encryption aes-256
protocol esp integrity sha-1 md5
crypto ipsec ikev2 ipsec-proposal AES192
protocol esp encryption aes-192
protocol esp integrity sha-1 md5
crypto ipsec ikev2 ipsec-proposal AES
protocol esp encryption aes
protocol esp integrity sha-1 md5
crypto ipsec ikev2 ipsec-proposal 3DES
protocol esp encryption 3des
protocol esp integrity sha-1 md5
crypto ipsec ikev2 ipsec-proposal DES
protocol esp encryption des
protocol esp integrity sha-1 md5
crypto ipsec security-association pmtu-aging infinite
crypto map Outside_map 1 match address Outside_cryptomap
crypto map Outside_map 1 set pfs group5
crypto map Outside_map 1 set peer 8.8.4.8
crypto map Outside_map 1 set ikev1 transform-set ESP-AES-256-SHA-TRANS ESP-AES-256-SHA
crypto map Outside_map 1 set security-association lifetime kilobytes unlimited
crypto map Outside_map 1 set nat-t-disable
crypto map Outside_map 2 match address Outside_cryptomap_1
crypto map Outside_map 2 set pfs group5
crypto map Outside_map 2 set peer 4.2.4.8
crypto map Outside_map 2 set ikev1 transform-set ESP-AES-256-SHA ESP-AES-256-SHA-TRANS
crypto map Outside_map 2 set security-association lifetime kilobytes unlimited
crypto map Outside_map 2 set nat-t-disable
crypto map Outside_map 3 match address Outside_cryptomap_2
crypto map Outside_map 3 set pfs group5
crypto map Outside_map 3 set peer 6.5.7.0
crypto map Outside_map 3 set ikev1 transform-set ESP-AES-256-SHA ESP-AES-256-SHA-TRANS
crypto map Outside_map 3 set security-association lifetime kilobytes unlimited
crypto map Outside_map 3 set nat-t-disable
crypto map Outside_map interface Outside
crypto ca trustpoint _SmartCallHome_ServerCA
no validation-usage
crl configure
crypto ca trustpool policy
crypto ca certificate chain _SmartCallHome_ServerCA
certificate ca 6ecc7aa5a7032009b8cebcf4e952d491
308205ec 308204d4 a0030201 0202106e cc7aa5a7 032009b8 cebcf4e9 52d49130
0d06092a 864886f7 0d010105 05003081 ca310b30 09060355 04061302 55533117
30150603 55040a13 0e566572 69536967 6e2c2049 6e632e31 1f301d06 0355040b
13165665 72695369 676e2054 72757374 204e6574 776f726b 313a3038 06035504
0b133128 63292032 30303620 56657269 5369676e 2c20496e 632e202d 20466f72
20617574 686f7269 7a656420 75736520 6f6e6c79 31453043 06035504 03133c56
65726953 69676e20 436c6173 73203320 5075626c 69632050 72696d61 72792043
65727469 66696361 74696f6e 20417574 686f7269 7479202d 20473530 1e170d31
30303230 38303030 3030305a 170d3230 30323037 32333539 35395a30 81b5310b
30090603 55040613 02555331 17301506 0355040a 130e5665 72695369 676e2c20
496e632e 311f301d 06035504 0b131656 65726953 69676e20 54727573 74204e65
74776f72 6b313b30 39060355 040b1332 5465726d 73206f66 20757365 20617420
68747470 733a2f2f 7777772e 76657269 7369676e 2e636f6d 2f727061 20286329
3130312f 302d0603 55040313 26566572 69536967 6e20436c 61737320 33205365
63757265 20536572 76657220 4341202d 20473330 82012230 0d06092a 864886f7
0d010101 05000382 010f0030 82010a02 82010100 b187841f c20c45f5 bcab2597
a7ada23e 9cbaf6c1 39b88bca c2ac56c6 e5bb658e 444f4dce 6fed094a d4af4e10
9c688b2e 957b899b 13cae234 34c1f35b f3497b62 83488174 d188786c 0253f9bc
7f432657 5833833b 330a17b0 d04e9124 ad867d64 12dc744a 34a11d0a ea961d0b
15fca34b 3bce6388 d0f82d0c 948610ca b69a3dca eb379c00 48358629 5078e845
63cd1941 4ff595ec 7b98d4c4 71b350be 28b38fa0 b9539cf5 ca2c23a9 fd1406e8
18b49ae8 3c6e81fd e4cd3536 b351d369 ec12ba56 6e6f9b57 c58b14e7 0ec79ced
4a546ac9 4dc5bf11 b1ae1c67 81cb4455 33997f24 9b3f5345 7f861af3 3cfa6d7f
81f5b84a d3f58537 1cb5a6d0 09e4187b 384efa0f 02030100 01a38201 df308201
db303406 082b0601 05050701 01042830 26302406 082b0601 05050730 01861868
7474703a 2f2f6f63 73702e76 65726973 69676e2e 636f6d30 12060355 1d130101
ff040830 060101ff 02010030 70060355 1d200469 30673065 060b6086 480186f8
45010717 03305630 2806082b 06010505 07020116 1c687474 70733a2f 2f777777
2e766572 69736967 6e2e636f 6d2f6370 73302a06 082b0601 05050702 02301e1a
1c687474 70733a2f 2f777777 2e766572 69736967 6e2e636f 6d2f7270 61303406
03551d1f 042d302b 3029a027 a0258623 68747470 3a2f2f63 726c2e76 65726973
69676e2e 636f6d2f 70636133 2d67352e 63726c30 0e060355 1d0f0101 ff040403
02010630 6d06082b 06010505 07010c04 61305fa1 5da05b30 59305730 55160969
6d616765 2f676966 3021301f 30070605 2b0e0302 1a04148f e5d31a86 ac8d8e6b
c3cf806a d448182c 7b192e30 25162368 7474703a 2f2f6c6f 676f2e76 65726973
69676e2e 636f6d2f 76736c6f 676f2e67 69663028 0603551d 11042130 1fa41d30
1b311930 17060355 04031310 56657269 5369676e 4d504b49 2d322d36 301d0603
551d0e04 1604140d 445c1653 44c1827e 1d20ab25 f40163d8 be79a530 1f060355
1d230418 30168014 7fd365a7 c2ddecbb f03009f3 4339fa02 af333133 300d0609
2a864886 f70d0101 05050003 82010100 0c8324ef ddc30cd9 589cfe36 b6eb8a80
4bd1a3f7 9df3cc53 ef829ea3 a1e697c1 589d756c e01d1b4c fad1c12d 05c0ea6e
b2227055 d9203340 3307c265 83fa8f43 379bea0e 9a6c70ee f69c803b d937f47a
6decd018 7d494aca 99c71928 a2bed877 24f78526 866d8705 404167d1 273aeddc
481d22cd 0b0b8bbc f4b17bfd b499a8e9 762ae11a 2d876e74 d388dd1e 22c6df16
b62b8214 0a945cf2 50ecafce ff62370d ad65d306 4153ed02 14c8b558 28a1ace0
5becb37f 954afb03 c8ad26db e6667812 4ad99f42 fbe198e6 42839b8f 8f6724e8
6119b5dd cdb50b26 058ec36e c4c875b8 46cfe218 065ea9ae a8819a47 16de0c28
6c2527b9 deb78458 c61f381e a4c4cb66
quit
crypto ikev2 policy 1
encryption aes-256
integrity sha
group 5 2
prf sha
lifetime seconds 86400
crypto ikev2 policy 10
encryption aes-192
integrity sha
group 5 2
prf sha
lifetime seconds 86400
crypto ikev2 policy 20
encryption aes
integrity sha
group 5 2
prf sha
lifetime seconds 86400
crypto ikev2 policy 30
encryption 3des
integrity sha
group 5 2
prf sha
lifetime seconds 86400
crypto ikev2 policy 40
encryption des
integrity sha
group 5 2
prf sha
lifetime seconds 86400
crypto ikev1 enable Inside
crypto ikev1 enable Outside
crypto ikev1 policy 1
authentication pre-share
encryption aes-256
hash sha
group 5
lifetime 28800
crypto ikev1 policy 2
authentication pre-share
encryption aes-256
hash md5
group 5
lifetime 28800
telnet 10.0.5.0 255.255.255.0 Inside
telnet timeout 5
no ssh stricthostkeycheck
ssh timeout 5
ssh key-exchange group dh-group1-sha1
console timeout 0
threat-detection basic-threat
threat-detection scanning-threat
threat-detection statistics
threat-detection statistics tcp-intercept rate-interval 30 burst-rate 400 average-rate 200
group-policy DfltGrpPolicy attributes
vpn-idle-timeout none
vpn-tunnel-protocol ikev1 ikev2 l2tp-ipsec
group-policy GroupPolicy_8.8.4.8 internal
group-policy GroupPolicy_8.8.4.8 attributes
vpn-tunnel-protocol ikev1
group-policy GroupPolicy_4.2.4.8 internal
group-policy GroupPolicy_4.2.4.8 attributes
vpn-tunnel-protocol ikev1
group-policy GroupPolicy_6.5.7.0 internal
group-policy GroupPolicy_6.5.7.0 attributes
vpn-tunnel-protocol ikev1
password-policy minimum-length 6
password-policy minimum-lowercase 1
password-policy minimum-uppercase 1
password-policy minimum-numeric 1
password-policy minimum-special 1
tunnel-group 8.8.4.8 type ipsec-l2l
tunnel-group 8.8.4.8 general-attributes
default-group-policy GroupPolicy_8.8.4.8
tunnel-group 8.8.4.8 ipsec-attributes
ikev1 pre-shared-key *****
ikev2 remote-authentication pre-shared-key *****
ikev2 local-authentication pre-shared-key *****
tunnel-group 4.2.4.8 type ipsec-l2l
tunnel-group 4.2.4.8 general-attributes
default-group-policy GroupPolicy_4.2.4.8
tunnel-group 4.2.4.8 ipsec-attributes
ikev1 pre-shared-key *****
ikev2 remote-authentication pre-shared-key *****
ikev2 local-authentication pre-shared-key *****
tunnel-group 6.5.7.0 type ipsec-l2l
tunnel-group 6.5.7.0 general-attributes
default-group-policy GroupPolicy_6.5.7.0
tunnel-group 6.5.7.0 ipsec-attributes
ikev1 pre-shared-key *****
ikev2 remote-authentication pre-shared-key *****
ikev2 local-authentication pre-shared-key *****
!
class-map inspection_default
match default-inspection-traffic
!
!
policy-map type inspect dns preset_dns_map
parameters
message-length maximum client auto
message-length maximum 512
policy-map global_policy
class inspection_default
inspect esmtp
inspect ctiqbe
inspect dcerpc
inspect dns
inspect ftp
inspect h323 h225
inspect h323 ras
inspect http
inspect icmp
inspect ip-options
inspect mgcp
inspect netbios
inspect pptp
inspect rsh
inspect rtsp
inspect sip
inspect skinny
inspect snmp
inspect sqlnet
inspect sunrpc
inspect tftp
inspect waas
inspect xdmcp
class class-default
user-statistics accounting
!
service-policy global_policy global
prompt hostname context
call-home reporting anonymous
hpm topN enable
Cryptochecksum:
: end
asdm history enable
 
I'm not an ASA guru but get my hands dirty now and then. That said, take these 2 things with a grain of salt...

1) Have you tried running packet-tracer for something like the hair-pin NAT you're trying to implement and see what happens? This will show you how it is currently NAT'ing and might help you figure it out.

2) If your workstations and servers are on the same LAN - how is the ASA intercepting the traffic? I would expect this to all be layer two via the switch(es) and normal traffic shouldn't hit the ASA. EDIT: I'm thinking in regards to issue 3 with the mapped drives. I suppose the hair-pin NAT you refer to was internal hosts hitting the web server via the public IP (retrieved via DNS)?
 
I'm not an ASA guru but get my hands dirty now and then. That said, take these 2 things with a grain of salt...

1) Have you tried running packet-tracer for something like the hair-pin NAT you're trying to implement and see what happens? This will show you how it is currently NAT'ing and might help you figure it out.

2) If your workstations and servers are on the same LAN - how is the ASA intercepting the traffic? I would expect this to all be layer two via the switch(es) and normal traffic shouldn't hit the ASA. EDIT: I'm thinking in regards to issue 3 with the mapped drives. I suppose the hair-pin NAT you refer to was internal hosts hitting the web server via the public IP (retrieved via DNS)?
Forgot I posted this here...

Issue 1: Still present, haven't put much work into getting it right though.

Issue 2: I've spent a few hours on this looking for an answer but still can't find it. I've put wireshark on the requestor and looked at the packet flow, the only thing coming and going are on ports 80 and 9675, both of which are opened up on the ASA. Additionally, ASDM has a real-time log viewer built-in that I used to look for dropped packets. After setting it up to log any packets implicitly dropped, I ran through and it doesn't show any packets being dropped in the data stream either.

Issue 3: This was a coincidental issue that cropped up at the same time as the ASA installation. This is actually the result of a Windows update that changes how GPOs are processed. I've implemented and verified the fix for this.
 
Keep the split brain DNS, forget the hairpin NAT, it will work out better for you.

If you are doing Acitve Directory anyways you want to use your internal DNS for your sites anyways. To give you an idea, I maintain our DNS, and there are times when I need to enter a DNS entry that the outside world doesn't need to know about even though it has our FQDN, and not our local AD DNS.

Hairpin NATs can be done, but I find that often times the firewall wants to think those are attacks and blocks them.

Depending on the size of the network, I have also gotten a switch capable of routing and set it up as my primary router for the network, so I can control routing inside the network if I have multiple VLANs.
 
does your ISP route that /28 to you via a /30 or /31?

If so you can variably subnet it inside your network (two /29 or four /30, not but sure why you'd want to do this)

My guess is you will have to NAT your internal traffic out to specific IP on the outside interface.

Like, if the ISP just presents you the gateway of the /28 (gateway on their end, layer two handoff) then you'll have to assign the next useable IP on your outside interface and use NAT statements to route your internal traffic to specific IP on the outside.
 
Oh boy, so I got everything sorted....

Issue 1: Left split-DNS in...this week was actually my last at the job so I just ran out of time to get hairpin NAT working.

Issue 2: This was a misconfiguration on the webserver by myself. So the ASA was translating port 80 requests to port 9675 which was then processed by Spiceworks' Apache webserver application. When I put the files not related to Spiceworks on the webserver, IIS was handling requests for them on port 80. So when someone requested a Spiceworks asset from the outside, it was on port 80 and translated to 9675. When a non-Spiceworks file was requested by an external user, it was done on port 80....but the ASA was still translating it to 9675 and Spiceworks didn't know where those files were. So I did some digging around, learned about virtual directories (IIS) and aliases (Apache) and relocated the files into the Apache assets folder, reconfigured my web code to point to the new location and everything started working as it should.
 
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