David, you should put an unfiltered reproducer on the internet.
> I can't connect to that host from where I am, obviously it does some
> sort of port 25 filtering or I would look at the certificate myself.
> instead of grepping strings it might be helpful to show the entire
> certificate.
>
> On Fri, Apr 10, 2020 at 12:13:24PM -0400, da...@goerger.info wrote:
> > I'm running OpenBSD-current on amd64 (dmesg below). I can test patches
> > but admit I got a bit lost this morning stepping through the certificate
> > verification code in usr.sbin/smtpd/{cert,mta_session,ssl_verify}.c
> > trying to debug this myself. I'll keep poking at it but would
> > appreciate any assistance or pointers in the right direction. Thanks!
> >
> > >Synopsis: ssl wildcard certificate verification failure
> > >Category: opensmtpd
> > >Environment:
> > System : OpenBSD 6.6
> > Details : OpenBSD 6.6-current (GENERIC) #105: Sun Apr 5 03:03:30
> > MDT 2020
> >
> > dera...@amd64.openbsd.org:/usr/src/sys/arch/amd64/compile/GENERIC
> >
> > Architecture: OpenBSD.amd64
> > Machine : amd64
> > >Description:
> >
> > Problem statement
> > -----------------
> > OpenSMTPD doesn't appear to recognise wildcard certificates as valid
> > when validating other relays' certificates.
> >
> >
> > Observation
> > -----------
> >
> > When sending a message to a contact with mail hosted by
> > e.g. "mx.hostedemail.com" (say postmas...@hostedemail.com),
> >
> > ===
> > # per /var/log/maillog
> >
> > Apr 9 14:23:08 ersa smtpd[18389]: 7516fbee48439810 mta connecting
> > address=smtp+tls://216.40.42.4:25 host=mx.hostedemail.com
> > Apr 9 14:23:08 ersa smtpd[18389]: 7516fbee48439810 mta connected
> > Apr 9 14:23:09 ersa smtpd[18389]: 7516fbee48439810 mta tls
> > ciphers=TLSv1.2:ECDHE-RSA-AES128-GCM-SHA256:128
> > Apr 9 14:23:09 ersa smtpd[18389]: 7516fbee48439810 mta error reason=SSL
> > certificate check failed
> > Apr 9 14:23:09 ersa smtpd[18389]: smtp-out: Disabling route [] <->
> > 216.40.42.4 (mx.hostedemail.com) for 15s
> >
> > # openssl certificate query
> > $ echo Q | openssl s_client -starttls smtp -connect mx.hostedemail.com:25
> > 2>/dev/null | openssl x509 -text | grep DNS
> > DNS:*.hostedemail.com, DNS:hostedemail.com
> > ===
> >
> >
> > Expected behaviour
> > ------------------
> >
> > The certificate SAN "*.hostedemail.com" should match for
> > "mx.hostedemail.com".
> >
> >
> > Relevant lines from smtpd.conf
> > ------------------------------
> >
> > I think the only relevant bit is that I set "relay tls" and not "relay
> > tls no-verify" - the latter config would pass mail outbound despite
> > the remote certificate validation failure.
> >
> > ===
> > pki ersa.daemonic.life cert "/etc/ssl/ersa.daemonic.life.fullchain.pem"
> > pki ersa.daemonic.life key "/etc/ssl/private/ersa.daemonic.life.key"
> > action "outbound" relay tls pki ersa.daemonic.life
> > match from local for any action outbound
> > ===
> >
> >
> >
> > dmesg:
> > OpenBSD 6.6-current (GENERIC) #105: Sun Apr 5 03:03:30 MDT 2020
> > dera...@amd64.openbsd.org:/usr/src/sys/arch/amd64/compile/GENERIC
> > real mem = 2130575360 (2031MB)
> > avail mem = 2053550080 (1958MB)
> > mpath0 at root
> > scsibus0 at mpath0: 256 targets
> > mainbus0 at root
> > bios0 at mainbus0: SMBIOS rev. 2.8 @ 0xf5720 (9 entries)
> > bios0: vendor SeaBIOS version "rel-1.12.0-0-ga698c8995f-prebuilt.qemu.org"
> > date 04/01/2014
> > bios0: QEMU Standard PC (i440FX + PIIX, 1996)
> > acpi0 at bios0: ACPI 1.0
> > acpi0: sleep states S3 S4 S5
> > acpi0: tables DSDT FACP APIC HPET
> > acpi0: wakeup devices
> > acpitimer0 at acpi0: 3579545 Hz, 24 bits
> > acpimadt0 at acpi0 addr 0xfee00000: PC-AT compat
> > cpu0 at mainbus0: apid 0 (boot processor)
> > cpu0: Intel(R) Xeon(R) CPU E5-2680 v3 @ 2.50GHz, 174.27 MHz, 06-3f-02
> > cpu0:
> > FPU,VME,DE,PSE,TSC,MSR,PAE,MCE,CX8,APIC,SEP,MTRR,PGE,MCA,CMOV,PAT,PSE36,CFLUSH,MMX,FXSR,SSE,SSE2,SS,SSE3,PCLMUL,SSSE3,FMA3,CX16,PCID,SSE4.1,SSE4.2,x2APIC,MOVBE,POPCNT,DEADLINE,AES,XSAVE,AVX,F16C,RDRAND,HV,NXE,PAGE1GB,RDTSCP,LONG,LAHF,ABM,PERF,FSGSBASE,TSC_ADJUST,BMI1,AVX2,SMEP,BMI2,ERMS,INVPCID,IBRS,IBPB,SSBD,ARAT,XSAVEOPT,MELTDOWN
> > cpu0: 64KB 64b/line 2-way I-cache, 64KB 64b/line 2-way D-cache, 512KB
> > 64b/line 16-way L2 cache
> > cpu0: ITLB 255 4KB entries direct-mapped, 255 4MB entries direct-mapped
> > cpu0: DTLB 255 4KB entries direct-mapped, 255 4MB entries direct-mapped
> > cpu0: smt 0, core 0, package 0
> > mtrr: Pentium Pro MTRR support, 8 var ranges, 88 fixed ranges
> > cpu0: apic clock running at 1000MHz
> > ioapic0 at mainbus0: apid 0 pa 0xfec00000, version 11, 24 pins
> > acpihpet0 at acpi0: 100000000 Hz
> > acpiprt0 at acpi0: bus 0 (PCI0)
> > acpicpu0 at acpi0: C1(@1 halt!)
> > "ACPI0006" at acpi0 not configured
> > acpipci0 at acpi0 PCI0: _OSC failed
> > acpicmos0 at acpi0
> > "PNP0A06" at acpi0 not configured
> > "PNP0A06" at acpi0 not configured
> > "PNP0A06" at acpi0 not configured
> > "QEMU0002" at acpi0 not configured
> > "ACPI0010" at acpi0 not configured
> > cpu0: using Broadwell MDS workaround
> > pvbus0 at mainbus0: KVM
> > pvclock0 at pvbus0
> > pci0 at mainbus0 bus 0
> > pchb0 at pci0 dev 0 function 0 "Intel 82441FX" rev 0x02
> > pcib0 at pci0 dev 1 function 0 "Intel 82371SB ISA" rev 0x00
> > pciide0 at pci0 dev 1 function 1 "Intel 82371SB IDE" rev 0x00: DMA, channel
> > 0 wired to compatibility, channel 1 wired to compatibility
> > wd0 at pciide0 channel 0 drive 0: <QEMU HARDDISK>
> > wd0: 16-sector PIO, LBA48, 50804MB, 104046592 sectors
> > wd0(pciide0:0:0): using PIO mode 4, DMA mode 2
> > pciide0: channel 1 disabled (no drives)
> > piixpm0 at pci0 dev 1 function 3 "Intel 82371AB Power" rev 0x03: apic 0 int
> > 9
> > iic0 at piixpm0
> > vga1 at pci0 dev 2 function 0 "Cirrus Logic CL-GD5446" rev 0x00
> > wsdisplay0 at vga1 mux 1: console (80x25, vt100 emulation)
> > wsdisplay0: screen 1-5 added (80x25, vt100 emulation)
> > em0 at pci0 dev 3 function 0 "Intel 82540EM" rev 0x03: apic 0 int 11,
> > address f2:3c:91:5a:d4:61
> > isa0 at pcib0
> > isadma0 at isa0
> > fdc0 at isa0 port 0x3f0/6 irq 6 drq 2
> > com0 at isa0 port 0x3f8/8 irq 4: ns16550a, 16 byte fifo
> > com0: console
> > pckbc0 at isa0 port 0x60/5 irq 1 irq 12
> > pckbd0 at pckbc0 (kbd slot)
> > wskbd0 at pckbd0: console keyboard, using wsdisplay0
> > pms0 at pckbc0 (aux slot)
> > wsmouse0 at pms0 mux 0
> > pcppi0 at isa0 port 0x61
> > spkr0 at pcppi0
> > vscsi0 at root
> > scsibus1 at vscsi0: 256 targets
> > softraid0 at root
> > scsibus2 at softraid0: 256 targets
> > root on wd0a (f628cab05ab35b0b.a) swap on wd0b dump on wd0b
> > fd0 at fdc0 drive 1: density unknown
> >
> > usbdevs:
> > usbdevs: no USB controllers found
> >
>
