A new IP Office won't allow trunk to trunk transfers (including forwards) to start with. You need to enable 'Allow Trunk to Trunk' transfer.

Anything you can add about the calls which forward and those that don't would help. For example, can internal calls be forwarded.

Stuck in a never ending cycle of file copying.

Perhaps you send the wrong caller ID with the outbound call and the provider drops the call.

IP Office remote service
IP Office certificate check
CLI based call blocking
SCN fallback over PSTN

run a monitor trace with SIP options enabled and post back, we can tell from there. But as Sizbut said check the allow forwarding option for both system and user.
Mike

Inhibit off-switch forward/transfer turned off? found in system>Telephony tab, tick box.

here is some monitor info.

********* SysMonitor v11.0.4.3.0 build 3 [connected to 192.168.43.1 (DMofAustin)] **********
08:54:26 601286607mS PRN: Monitor Status IP 500 V2 11.0.0.0.0 build 849
08:54:26 601286607mS PRN: LAW=U PRI=0, BRI=0, ALOG=4, VCOMP=10, MDM=0, WAN=0, MODU=0 LANM=0 CkSRC=0 VMAIL=1(VER=2 TYP=3) 1-X=0 CALLS=1(TOT=1752)
08:54:27 601287516mS CMExtnRx: v=222, p1=0
CMReleaseComp
Line: type=AnalogueExtn 4 Call: lid=0 id=6 in=0
08:54:27 601287516mS CMCallEvt: c0a82cfa00004e84 0.20100.0 1752 Extn222.0: StateChange: END=A CMCSConnected->CMCSCompleted
08:54:27 601287517mS CMExtnEvt: v=6 State, new=PortRecoverDelay old=Connected,0,0,Extn222
08:54:27 601287518mS CMLOGGING: CALL:2020/08/2608:54,00:00:04,006,222,O,214,214,Extn222,,,1,,"",0,n/a
08:54:27 601287518mS CMExtnEvt: Extn222: CALL LOST (CMCauseNormal)
08:54:27 601287518mS CMExtnEvt: Extn222: Extn(222) Calling Party Number(222) Type(CMNTypeInternal)
08:54:27 601287518mS CMExtnEvt: Extn222: CMExtnHandler::SetCurrent( id: 20100->0 )
08:54:27 601287519mS CMCallEvt: c0a82cfa00004e84 0.20100.0 -1 Extn222.-1: StateChange: END=X CMCSCompleted->CMCSDelete
08:54:27 601287519mS CMExtnEvt: RAS: CALL LOST (CMCauseNormal)
08:54:27 601287519mS CMCallEvt: c0a82cfa00004e86 0.20102.0 -1 RAS.0: StateChange: END=X CMCSConnected->CMCSCompleted
08:54:27 601287519mS CMExtnEvt: v=1011 State, new=PortRecoverDelay old=Connected,0,0,RAS
08:54:27 601287519mS CMExtnTx: v=RAS, p1=0
CMReleaseComp
Line: type=RAS 1 Call: lid=0 id=1011 in=0
Called[#Extn214] Type=Voicemail (102) Reason=107 Calling[222] Type=Internal Plan=Default
BChan: slot=21 chan=42
Cause=16, Normal call clearing
08:54:27 601287520mS CMMap: a=21.42 b=0.0 T0
08:54:27 601287521mS CMExtnEvt: RAS: CMExtnHandler::SetCurrent( id: 20102->0 )
08:54:27 601287521mS CMCallEvt: c0a82cfa00004e86 0.20102.0 -1 RAS.-1: StateChange: END=X CMCSCompleted->CMCSDelete
08:54:27 601287521mS CMExtnEvt: v=1011 State, new=Idle old=PortRecoverDelay,0,0,RAS
08:54:27 601287522mS CMExtnTx: v=RAS, p1=0
CMReleaseComp
Line: type=RAS 1 Call: lid=0 id=1011 in=0
BChan: slot=21 chan=42
Cause=16, Normal call clearing
08:54:27 601287522mS CMCallEvt: c0a82cfa00004e86 0.20102.0 -1 BaseEP: DELETE CMEndpoint f1720efc TOTAL NOW=1 CALL_LIST=0
08:54:27 601287522mS CMCallEvt: END CALL:1752 (f1783b3c)
08:54:27 601287523mS CMCallEvt: c0a82cfa00004e84 0.20100.0 -1 BaseEP: DELETE CMEndpoint f174e4d4 TOTAL NOW=0 CALL_LIST=0
08:54:27 601287523mS CMExtnTx: v=214, p1=0
CMVoiceMailStatus
Line: type=DigitalExtn 3 Call: lid=0 id=-1 in=0
Called[Extn214 Msgs=1 Old=0 Sav=0] Type=Default (100) Reason=CMDRdirect Calling[00000001] Type=Default Plan=Default
Display [Extn214 Msgs=1]
Timed: 26/08/20 08:54
08:54:27 601287526mS CMMap: a=4.22 b=21.42 CheckSpeechPathMonitor (pcp[22]b1r0) unregister
08:54:27 601287526mS PRN: Confer DSP: channel 0 disabled DTMF detector 0(0)
08:54:27 601287526mS PRN: Confer DSP: channel 0: freed DTMF detector 0, 24 free
08:54:27 601287526mS CMMap: PCG::UnmapBChan pcp[22]b1r0 cp_b f566fda0 other_cp_b f562bd04
08:54:27 601287526mS CMMap: a=4.22 b=21.42 M02
08:54:27 601287526mS CMMap: PCG::UnmapBChan pcp[79]b1r0 cp_b f562bd04 other_cp_b 0
08:54:27 601287543mS PRN: FlashA: popen: A:\system\dynamic\lvmail\.c11 Open Failed
08:54:27 601287543mS PRN: FlashA: CloseFlashItem: File Open Failed (2)
08:54:27 601287543mS PRN: FlashMan: ServiceAppendQueue: Failed to Add Item to FlashManagement List ----
---- User Name: ꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪꪪ￿￿￿￿￿￿￿￿ۿ￿&岼滿￿ Recorded at: 2060/09/25 04:18:50
08:54:27 601287544mS PRN: FlashA: DiscardFlashItem: File 0 Delete Fai 08:54:29 601289519mS CMExtnEvt: Extn222: Recover Timer reason=CMTRWrapUp
08:54:29 601289519mS CMExtnEvt: v=6 State, new=Idle old=PortRecoverDelay,0,0,Extn222
08:54:30 601290065mS RES: Wed 26/8/2020 08:54:30 FreeMem=57339744 Heap=56758632(3) Cache=581112 MemObjs=9390(Max 11325) CMMsg=5(6) ASN=0 Buff=5200 1363 1000 7444 5 Links=52697(53025) BTree=491(1348) CB=6072 MCT=0 CPU=20.63% CPUStats=12.05%/1/4/2811/1555
5/19347/00.11%/1/02.54% MCR=0 MCW=0 DEV=0
08:54:30 601290066mS RES2: IP 500 V2 11.0.0.0.0 build 849 Tasks=52 RTEngine=0 CMRTEngine=0 ExRTEngine=0 Timer=11+51 Poll=0 Ready=0 CMReady=0 CMQueue=0 VPNNQueue=0 Monitor=1 SSA=1 TCP=20(TLS=5 OFF=0) TAPI=0 Partner=0 ASC=1 SYS=MNTD OPT=UMNT SDSPD=2034
08:54:30 601290066mS RES4: XML MemObjs=8 PoolMem=4748404(2) FreeMem=4736284(0) HeapUsed=0
08:54:30 601290066mS RES5: CLog MemObjs=389 FreePoolMem(Objs)=5772(111) TotalMem=26000 StringsTotalMem=80150

Here is the SIP info

********** SysMonitor v11.0.4.3.0 build 3 [connected to 192.168.43.1 (DMofAustin)] **********
08:58:38 601538621mS PRN: Monitor Status IP 500 V2 11.0.0.0.0 build 849
08:58:38 601538621mS PRN: LAW=U PRI=0, BRI=0, ALOG=4, VCOMP=10, MDM=0, WAN=0, MODU=0 LANM=0 CkSRC=0 VMAIL=1(VER=2 TYP=3) 1-X=0 CALLS=0(TOT=1752)
08:58:49 601549354mS CMCallEvt: 0000000000000000 0.20107.0 -1 BaseEP: NEW CMEndpoint f4fb82f8 TOTAL NOW=1 CALL_LIST=0
08:58:49 601549354mS NAT: Info: Line 17: Not using STUN for media in this case.
08:58:49 601549356mS SIP Tx: UDP 192.168.44.250:5060 -> 204.11.192.39:5080
REGISTER sip:callcentric.com SIP/2.0
Via: SIP/2.0/UDP 192.168.44.250:5060;rport;branch=z9hG4bK130b699526e486c842e78ba4398ba88e
From: <sip:17778585078@callcentric.com>;tag=7f8232bf4635d234
To: <sip:17778585078@callcentric.com>
Call-ID: 9993cda30ee58662cf0bee0eea5286e9
CSeq: 1173740853 REGISTER
Contact: <sip:17778585078@192.168.44.250:5060;transport=udp>
Expires: 3600
Proxy-Authorization: Digest username="17778585078",realm="callcentric.com",nonce="91b2472561211d44299f8d8989d803da",response="b61a6c1d38cfdfbe9dede3d4d5853642",uri="sip:callcentric.com"
Max-Forwards: 70
User-Agent: IP Office 11.0.0.0.0 build 849
Supported: timer
Content-Length: 0

08:58:49 601549426mS SIP Rx: UDP 204.11.192.39:5080 -> 192.168.44.250:5060
SIP/2.0 200 Ok
v: SIP/2.0/UDP 192.168.44.250:5060;rport=5060;branch=z9hG4bK130b699526e486c842e78ba4398ba88e;received=70.123.10.154
f: <sip:17778585078@callcentric.com>;tag=7f8232bf4635d234
t: <sip:17778585078@callcentric.com>
i: 9993cda30ee58662cf0bee0eea5286e9
CSeq: 1173740853 REGISTER
m: <sip:17778585078@192.168.44.250:5060;transport=udp>;expires=121
l: 0

It contains no information.

IP Office remote service
IP Office certificate check
CLI based call blocking
SCN fallback over PSTN

As derfloh said, these traces have no info. Have you check what other guys mentioned? Is this ONLY failing for analog extension? please provide another complete trace!