I had a request for more information about how to replicate this. Here's a stripped back example that demonstrates the problem.

paul@tiger:~/workspace/push/cm: cat ./distfile
./hosts/aspireone/etc/doas.conf -> ${HOST}
        install staging/etc ;


paul@tiger:~/workspace/push/cm: cat ./hosts/aspireone/etc/doas.conf
# This is a dummy file.


First attempt fails to create a file if two new directories have been created:

paul@tiger:~/workspace/push/cm: /usr/bin/rdist -L syslog=all -d HOST=aspireone
aspireone: updating host aspireone
aspireone: ./hosts/aspireone/etc/doas.conf: installing
aspireone: staging: mkdir
aspireone: staging/etc: mkdir
aspireone: REMOTE ERROR: staging/etc/rdist9lu2tvqg: create failed: Invalid argument
aspireone: updating of aspireone finished


Second pass succeeds:

paul@tiger:~/workspace/push/cm: /usr/bin/rdist -L syslog=all -d HOST=aspireone
aspireone: updating host aspireone
aspireone: ./hosts/aspireone/etc/doas.conf: installing
aspireone: updating of aspireone finished



dmesg from the remote machine:

OpenBSD 5.8-stable (GENERIC.MP) #1: Thu Nov 12 09:27:53 CET 2015
    paul@buildbox:/usr/src/sys/arch/i386/compile/GENERIC.MP
RTC BIOS diagnostic error 80<clock_battery>
cpu0: Intel(R) Atom(TM) CPU N270 @ 1.60GHz ("GenuineIntel" 686-class) 1.60 GHz cpu0: FPU,V86,DE,PSE,TSC,MSR,PAE,MCE,CX8,APIC,SEP,MTRR,PGE,MCA,CMOV,PAT,CFLUSH,DS,ACPI,MMX,FXSR,SSE,SSE2,SS,HTT,TM,PBE,SSE3,DTES64,MWAIT,DS-CPL,EST,TM2,SSSE3,xTPR,PDCM,MO
VBE,LAHF,PERF,SENSOR
real mem  = 1596956672 (1522MB)
avail mem = 1552547840 (1480MB)
mpath0 at root
scsibus0 at mpath0: 256 targets
mainbus0 at root
bios0 at mainbus0: date 10/06/08, SMBIOS rev. 2.4 @ 0xe9180 (32 entries)
bios0: vendor Acer version "v0.3309" date 10/06/2008
bios0: Acer AOA150
acpi0 at bios0: rev 2
acpi0: sleep states S0 S3 S4 S5
acpi0: tables DSDT FACP SSDT HPET APIC MCFG ASF! SLIC BOOT
acpi0: wakeup devices P32_(S4) UHC1(S3) UHC2(S3) UHC3(S3) UHC4(S3) ECHI(S3) EXP1(S4) EXP2(S4) EXP3(S4) EXP4(S4) AZAL(S0) MODM(S0)
acpitimer0 at acpi0: 3579545 Hz, 24 bits
acpihpet0 at acpi0: 14318179 Hz
acpimadt0 at acpi0 addr 0xfee00000: PC-AT compat
cpu0 at mainbus0: apid 0 (boot processor)
mtrr: Pentium Pro MTRR support, 8 var ranges, 88 fixed ranges
cpu0: apic clock running at 132MHz
cpu0: mwait min=64, max=64, C-substates=0.2.2.0.2, IBE
cpu1 at mainbus0: apid 1 (application processor)
cpu1: Intel(R) Atom(TM) CPU N270 @ 1.60GHz ("GenuineIntel" 686-class) 1.60 GHz cpu1: FPU,V86,DE,PSE,TSC,MSR,PAE,MCE,CX8,APIC,SEP,MTRR,PGE,MCA,CMOV,PAT,CFLUSH,DS,ACPI,MMX,FXSR,SSE,SSE2,SS,HTT,TM,PBE,SSE3,DTES64,MWAIT,DS-CPL,EST,TM2,SSSE3,xTPR,PDCM,MO
VBE,LAHF,PERF,SENSOR
ioapic0 at mainbus0: apid 4 pa 0xfec00000, version 20, 24 pins
ioapic0: misconfigured as apic 0, remapped to apid 4
acpimcfg0 at acpi0 addr 0xe0000000, bus 0-255
acpiprt0 at acpi0: bus 0 (PCI0)
acpiprt1 at acpi0: bus 5 (P32_)
acpiprt2 at acpi0: bus 1 (EXP1)
acpiprt3 at acpi0: bus 2 (EXP2)
acpiprt4 at acpi0: bus 3 (EXP3)
acpiprt5 at acpi0: bus 4 (EXP4)
acpiec0 at acpi0
acpicpu0 at acpi0: !C3(100@57 io@0x416), !C2(500@1 io@0x414), C1(1000@1 halt), PSS acpicpu1 at acpi0: !C3(100@57 io@0x416), !C2(500@1 io@0x414), C1(1000@1 halt), PSS
acpibtn0 at acpi0: PWRB
acpibtn1 at acpi0: LID0
acpibtn2 at acpi0: SLPB
acpibat0 at acpi0: BAT1 not present
acpiac0 at acpi0: AC unit online
acpivideo0 at acpi0: OVGA
bios0: ROM list: 0xc0000/0xec00!
cpu0: Enhanced SpeedStep 1596 MHz: speeds: 1600, 1333, 1066, 800 MHz
pci0 at mainbus0 bus 0: configuration mode 1 (bios)
pchb0 at pci0 dev 0 function 0 "Intel 82945GME Host" rev 0x03
vga1 at pci0 dev 2 function 0 "Intel 82945GME Video" rev 0x03
intagp0 at vga1
agp0 at intagp0: aperture at 0x60000000, size 0x10000000
inteldrm0 at vga1
drm0 at inteldrm0
inteldrm0: 1024x600
wsdisplay0 at vga1 mux 1: console (std, vt100 emulation)
wsdisplay0: screen 1-5 added (std, vt100 emulation)
"Intel 82945GM Video" rev 0x03 at pci0 dev 2 function 1 not configured
azalia0 at pci0 dev 27 function 0 "Intel 82801GB HD Audio" rev 0x02: msi
azalia0: codecs: Realtek ALC268
audio0 at azalia0
ppb0 at pci0 dev 28 function 0 "Intel 82801GB PCIE" rev 0x02: apic 4 int 16
pci1 at ppb0 bus 1
ppb1 at pci0 dev 28 function 1 "Intel 82801GB PCIE" rev 0x02: apic 4 int 17
pci2 at ppb1 bus 2
2:0:0: mem address conflict 0xfffe0000/0x20000
re0 at pci2 dev 0 function 0 "Realtek 8101E" rev 0x02: RTL8102EL (0x2480), msi, address 00:1e:68:cc:c0:06
rlphy0 at re0 phy 7: RTL8201L 10/100 PHY, rev. 1
ppb2 at pci0 dev 28 function 2 "Intel 82801GB PCIE" rev 0x02: apic 4 int 18
pci3 at ppb2 bus 3
wpi0 at pci3 dev 0 function 0 "Intel PRO/Wireless 3945ABG" rev 0x02: msi, MoW1, address 00:1c:bf:a9:21:f8
ppb3 at pci0 dev 28 function 3 "Intel 82801GB PCIE" rev 0x02: apic 4 int 19
pci4 at ppb3 bus 4
uhci0 at pci0 dev 29 function 0 "Intel 82801GB USB" rev 0x02: apic 4 int 16
uhci1 at pci0 dev 29 function 1 "Intel 82801GB USB" rev 0x02: apic 4 int 17
uhci2 at pci0 dev 29 function 2 "Intel 82801GB USB" rev 0x02: apic 4 int 18
uhci3 at pci0 dev 29 function 3 "Intel 82801GB USB" rev 0x02: apic 4 int 19
ehci0 at pci0 dev 29 function 7 "Intel 82801GB USB" rev 0x02: apic 4 int 16
usb0 at ehci0: USB revision 2.0
uhub0 at usb0 "Intel EHCI root hub" rev 2.00/1.00 addr 1
ppb4 at pci0 dev 30 function 0 "Intel 82801BAM Hub-to-PCI" rev 0xe2
pci5 at ppb4 bus 5
ichpcib0 at pci0 dev 31 function 0 "Intel 82801GBM LPC" rev 0x02: PM disabled pciide0 at pci0 dev 31 function 2 "Intel 82801GBM SATA" rev 0x02: DMA, channel 0 wired to compatibility, channel 1 wired to compatibility
wd0 at pciide0 channel 0 drive 0: <WDC WD1200BEVS-22UST0>
wd0: 16-sector PIO, LBA48, 114473MB, 234441648 sectors
wd0(pciide0:0:0): using PIO mode 4, Ultra-DMA mode 6
ichiic0 at pci0 dev 31 function 3 "Intel 82801GB SMBus" rev 0x02: apic 4 int 17
iic0 at ichiic0
spdmem0 at iic0 addr 0x51: 1GB DDR2 SDRAM non-parity PC2-5300CL5 SO-DIMM
usb1 at uhci0: USB revision 1.0
uhub1 at usb1 "Intel UHCI root hub" rev 1.00/1.00 addr 1
usb2 at uhci1: USB revision 1.0
uhub2 at usb2 "Intel UHCI root hub" rev 1.00/1.00 addr 1
usb3 at uhci2: USB revision 1.0
uhub3 at usb3 "Intel UHCI root hub" rev 1.00/1.00 addr 1
usb4 at uhci3: USB revision 1.0
uhub4 at usb4 "Intel UHCI root hub" rev 1.00/1.00 addr 1
isa0 at ichpcib0
isadma0 at isa0
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
npx0 at isa0 port 0xf0/16: reported by CPUID; using exception 16
uvideo0 at uhub0 port 5 configuration 1 interface 0 "SuYin Acer Crystal Eye webcam" rev 2.00/0.01 addr 2
video0 at uvideo0
uplcom0 at uhub1 port 1 "Prolific Technology Inc. USB-Serial Controller" rev 1.10/3.00 addr 2
ucom0 at uplcom0
uhidev0 at uhub1 port 2 configuration 1 interface 0 "Primax HP USB Keyboard" rev 1.10/1.11 addr 3
uhidev0: iclass 3/1
ukbd0 at uhidev0: 8 variable keys, 6 key codes
wskbd1 at ukbd0 mux 1
wskbd1: connecting to wsdisplay0
uhidev1 at uhub1 port 2 configuration 1 interface 1 "Primax HP USB Keyboard" rev 1.10/1.11 addr 3
uhidev1: iclass 3/0, 2 report ids
uhid0 at uhidev1 reportid 1: input=1, output=0, feature=0
uhid1 at uhidev1 reportid 2: input=2, output=0, feature=0
vscsi0 at root
scsibus1 at vscsi0: 256 targets
softraid0 at root
scsibus2 at softraid0: 256 targets
root on wd0a (0cf48e5840658f4b.a) swap on wd0b dump on wd0b

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