BUMP I just realised that terminal #2 uses a Cisco SPA112 converter. Since I am the admin of this device too, I turned off T.38 there, and now the scenario looks more promising, but there is still an error at the end of the transmission.
-- Attempting call on PJSIP/mytrunk/sip:<TOPHONENR>@my.sip-provider.com for faxout@fax_outgoing:1 (Retry 1)
-- Called mytrunk/sip:<TOPHONENR>@my.sip-provider.com
-- PJSIP/mytrunk-00000001 is ringing
> 0x7f1ac801d020 -- Strict RTP learning after remote address set to: 91.xxx.xxx.xxx:10270
-- PJSIP/mytrunk-00000001 answered
-- Executing [faxout@fax_outgoing:1] NoOp("PJSIP/mytrunk-00000001", "**** SENDING FAX ****") in new stack
-- Executing [faxout@fax_outgoing:2] Wait("PJSIP/mytrunk-00000001", "2") in new stack
-- Executing [faxout@fax_outgoing:3] Set("PJSIP/mytrunk-00000001", "FAXFILE=Asterisk_SendFax_res_fax.tif") in new stack
-- Executing [faxout@fax_outgoing:4] SendFAX("PJSIP/mytrunk-00000001", "/var/spool/asterisk/tmp/Asterisk_SendFax_res_fax.tif,dfsz") in new stack
-- Channel 'PJSIP/mytrunk-00000001' sending FAX:
-- /var/spool/asterisk/tmp/Asterisk_SendFax_res_fax.tif
> 0x7f1ac801d020 -- Strict RTP switching to RTP target address 91.xxx.xxx.xxx:10270 as source
> 0x7f1ac801d020 -- Strict RTP learning complete - Locking on source address 91.xxx.xxx.xxx:10270
[May 29 17:46:21] WARNING[13209][C-00000002]: res_fax.c:2412 sendfax_t38_init: channel 'PJSIP/mytrunk-00000001' refused to negotiate T.38
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 000.520115 ], stack sent 25 frames (500 ms) of energy.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 002.378527 ], channel sent 118 frames (2360 ms) of silence.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 004.698080 ], channel sent 116 frames (2320 ms) of energy.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 004.760102 ], stack sent 212 frames (4240 ms) of silence.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 006.740078 ], stack sent 99 frames (1980 ms) of energy.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 006.800081 ], stack sent 3 frames (60 ms) of silence.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 007.858076 ], channel sent 158 frames (3160 ms) of silence.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 009.720097 ], stack sent 146 frames (2920 ms) of energy.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 010.178572 ], channel sent 116 frames (2320 ms) of energy.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 013.260088 ], stack sent 177 frames (3540 ms) of silence.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 013.358695 ], channel sent 159 frames (3180 ms) of silence.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 015.260092 ], stack sent 100 frames (2000 ms) of energy.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 015.320163 ], stack sent 3 frames (60 ms) of silence.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 015.657857 ], channel sent 115 frames (2300 ms) of energy.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 018.240127 ], stack sent 146 frames (2920 ms) of energy.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 018.838800 ], channel sent 159 frames (3180 ms) of silence.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 021.158374 ], channel sent 116 frames (2320 ms) of energy.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 021.220118 ], stack sent 149 frames (2980 ms) of silence.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 023.220095 ], stack sent 100 frames (2000 ms) of energy.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 023.280089 ], stack sent 3 frames (60 ms) of silence.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 024.318631 ], channel sent 158 frames (3160 ms) of silence.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 026.200088 ], stack sent 146 frames (2920 ms) of energy.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 026.638164 ], channel sent 116 frames (2320 ms) of energy.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 029.718265 ], channel sent 154 frames (3080 ms) of silence.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 029.740124 ], stack sent 177 frames (3540 ms) of silence.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 030.860086 ], stack sent 56 frames (1120 ms) of energy.
Channel 'PJSIP/mytrunk-00000001' fax session '1', [ 030.978659 ], channel sent 63 frames (1260 ms) of energy.
-- Auto fallthrough, channel 'PJSIP/mytrunk-00000001' status is 'UNKNOWN'
-- Executing [h@fax_outgoing:1] NoOp("PJSIP/mytrunk-00000001", "** Hung up **") in new stack
-- Executing [h@fax_outgoing:2] GotoIf("PJSIP/mytrunk-00000001", "0?FaxDLR:hFail") in new stack
-- Goto (fax_outgoing,h,9)
-- Executing [h@fax_outgoing:9] NoOp("PJSIP/mytrunk-00000001", "Failed") in new stack
-- Executing [h@fax_outgoing:10] Set("PJSIP/mytrunk-00000001", "pages=0") in new stack
-- Executing [h@fax_outgoing:11] Set("PJSIP/mytrunk-00000001", "status=failed") in new stack
-- Executing [h@fax_outgoing:12] Set("PJSIP/mytrunk-00000001", "statusstr=failed") in new stack
-- Executing [h@fax_outgoing:13] Set("PJSIP/mytrunk-00000001", "error=Received no response to DCS or TCF") in new stack
-- Executing [h@fax_outgoing:14] NoOp("PJSIP/mytrunk-00000001", "** Sending Delivery Notification **") in new stack
-- Executing [h@fax_outgoing:15] NoOp("PJSIP/mytrunk-00000001", "** READY **") in new stack
[May 29 17:46:56] NOTICE[13209][C-00000002]: pbx_spool.c:463 attempt_thread: Call completed to PJSIP/mytrunk/sip:<TOPHONENR>@my.sip-provider.com