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Perfect, that was the hunch I was working with, but didn't realize it was an OS limitation. Makes more sense now that I think about it. Appreciate your insight, it's extremely helpful!

I've tested your batch file. It does not work at all on Windows 10 for me.
It seems that cmd.exe cannot even handle a command-line that long. When I run the batch file, it does not pass whole command-line to WinSCP. And last line passed [not the last line in the batch file] indeed misses one character.

You can see that on console output, when it prints the command being executed. So it's clear that it's not problem on WinSPC side. The rest of the command-line is then executed separately (obviously failing, as it's not valid Windows command):

B:\lws\1005>"C:\Program Files (x86)\WinSCP\"   /log="outfiles_20181009_.log" /ini=nul   /command     "open FTPINFO"     "put c:\outfiles\001152.out 001152.out"    "put c:\outfiles\002152.out 002152.out"     "put c:\outfiles\003152.out 003152.out"     "put c:\outfiles\004152.out 004152.out"     "put c:\outfiles\007152.out 007152.out"    "open FTPINFO"    "put c:\outfiles\196101.out 196101.OUT"    "open FTPINFO"    "put c:\outfiles\101235.out 101235.out"    "put c:\outfiles\108199.out 108199.out"    "open FTPINFO"     "put c:\outfiles\011057.out 011057.OUT"    "put c:\outfiles\012057.out 012057.OUT"    "put c:\outfiles\021057.out 021057.OUT"    "put c:\outfiles\022057.out 022057.OUT"    "put c:\outfiles\031057.out 031057.OUT"    "put c:\outfiles\032057.out 032057.OUT"    "put c:\outfiles\033057.out 033057.OUT"    "put c:\outfiles\041057.out 041057.OUT"    "put c:\outfiles\042057.out 042057.OUT"    "put c:\outfiles\051057.out 051057.OUT"    "put c:\outfiles\052057.out 052057.OUT"    "open FTPINFO"     "put c:\outfiles\116061.out 116061.out"    "open FTPINFO"    "cd out"    "put c:\outfiles\103137.out 103137.out"    "open FTPINFO"     "put c:\outfiles\101227.out 101227.out"    "open FTPINFO"     "put c:\outfiles\109220.out 109220.out"    "open FTPINFO"     "put c:\outfiles\101105.out 101105.out"    "open FTPINFO"     "put c:\outfiles\102165.out 102165.out"    "open FTPINFO"     "put c:\outfiles\001191.out 001191.out"    "put c:\outfiles\004191.out 004191.out"    "put c:\outfiles\007191.out 007191.out"    "put c:\outfiles\009191.out 009191.out"    "put c:\outfiles\090108.out 090108.out"    "open FTPINFO"     "put c:\outfiles\001023.out 001023.out"    "open FTPINFO"     "put c:\outfiles\102021.out 102021.out"    "open FTPINFO"     "put c:\outfiles\002144.out 002144.out"     "put c:\outfiles\009144.out 009144.out"    "put c:\outfiles\009057.out 009057.out"    "open FTPINFO"     "put c:\outfiles\000064.out 000064.out"    "put c:\outfiles\001175.out 001175.out"    "put c:\outfiles\002064.out 002064.out"    "put c:\outfiles\002175.out 002175.out"    "put c:\outfiles\003064.out 003064.out"    "put c:\outfiles\003175.out 003175.out"    "put c:\outfiles\004064.out 004064.out"    "put c:\outfiles\004175.out 004175.out"    "open FTPINFO"     "put c:\outfiles\011101.out 011101.out"    "put c:\outfiles\012101.out 012101.out"    "put c:\outfiles\013101.out 013101.out"    "put c:\outfiles\014101.out 014101.out"    "put c:\outfiles\015101.out 015101.out"    "put c:\outfiles\016101.out 016101.out"    "put c:\outfiles\017101.out 017101.out"    "put c:\outfiles\018101.out 018101.out"    "put c:\outfiles\021101.out 021101.out"    "put c:\outfiles\022101.out 022101.out"    "put c:\outfiles\023101.out 023101.out"    "put c:\outfiles\024101.out 024101.out"    "put c:\outfiles\025101.out 025101.out"    "put c:\outfiles\026101.out 026101.out"    "put c:\outfiles\027101.out 027101.out"    "put c:\outfiles\028101.out 028101.out"    "open FTPINFO"     "cd OUT"    "put c:\outfiles\102071.out 102071.out"    "open FTPINFO"     "put c:\outfiles\011014.out 011014.out"    "put c:\outfiles\021014.out 021014.out"    "put c:\outfiles\031014.out 031014.out"    "put c:\outfiles\032014.out 032014.out"    "put c:\outfiles\041014.out 041014.out"    "put c:\outfiles\042014.out 042014.out"    "open FTPINFO"     "put c:\outfiles\002123.out 002123.out"    "put c:\outfiles\004123.out 004123.out"    "put c:\outfiles\006123.out 006123.out"    "put c:\outfiles\007123.out 007123.out"    "put c:\outfiles\008123.out 008123.out"    "put c:\outfiles\011123.out 011123.out"    "put c:\outfiles\012123.out 012123.out"    "open FTPINFO"     "put c:\outfiles\110031.out 110031.out"    "put c:\outfiles\110109.out 110109.out"     "open FTPINFO"     "put c:\outfiles\003015.out 003015.out"    "put c:\outfiles\004015.out 004015.out"    "put c:\outfiles\011015.out 011015.out"    "put c:\outfiles\013015.out 013015.out"    "put c:\outfiles\022015.out 022015.out"    "open FTPINFO"     "put c:\outfiles\000047.out 000047.OUT"    "put c:\outfiles\000061.out 000061.OUT"    "put c:\outfiles\000080.out 000080.OUT"    "put c:\outfiles\000122.out 000122.OUT"    "put c:\outfiles\000134.out 000134.OUT"    "put c:\outfiles\000151.out 000151.OUT"    "put c:\outfiles\000157.out 000157.OUT"    "put c:\outfiles\000167.out 000167.OUT"    "put c:\outfiles\000168.out 000168.OUT"    "put c:\outfiles\000194.out 000194.OUT"    "put c:\outfiles\000196.out 000196.OUT"    "put c:\outfiles\000221.out 000221.OUT"    "put c:\outfiles\001001.out 001001.OUT"    "put c:\outfiles\001012.out 001012.OUT"    "put c:\outfiles\001013.out 001013.OUT"    "put c:\outfiles\001016.out 001016.OUT"    "put c:\outfiles\001018.out 001018.OUT"    "put c:\outfiles\001025.out 001025.OUT"    "put c:\outfiles\001028.out 001028.OUT"    "put c:\outfiles\001034.out 001034.OUT"    "put c:\outfiles\001036.out 001036.OUT"    "put c:\outfiles\001040.out 001040.OUT"    "put c:\outfiles\001041.out 001041.OUT"    "put c:\outfiles\001045.out 001045.OUT"    "put c:\outfiles\001055.out 001055.OUT"    "put c:\outfiles\001067.out 001067.OUT"    "put c:\outfiles\001069.out 001069.OUT"    "put c:\outfiles\001072.out 001072.OUT"    "put c:\outfiles\001073.out 001073.OUT"    "put c:\outfiles\001088.out 001088.OUT"    "put c:\outfiles\001107.out 001107.OUT"    "put c:\outfiles\001111.out 001111.OUT"    "put c:\outfiles\001112.out 001112.OUT"    "put c:\outfiles\001126.out 001126.OUT"    "put c:\outfiles\001146.out 001146.OUT"    "put c:\outfiles\001149.out 001149.OUT"    "put c:\outfiles\001150.out 001150.OUT"    "put c:\outfiles\001158.out 001158.OUT"    "put c:\outfiles\001168.out 001168.OUT"    "put c:\outfiles\001170.out 001170.OUT"    "put c:\outfiles\001174.out 001174.OUT"    "put c:\outfiles\001176.out 001176.OUT"    "put c:\outfiles\001179.out 001179.OUT"    "put c:\outfiles\001181.out 001181.OUT"    "put c:\outfiles\001183.out 001183.OUT"    "put c:\outfiles\001185.out 001185.OUT"    "put c:\outfiles\001202.out 001202.OUT"    "put c:\outfiles\001203.out 001203.OUT"    "put c:\outfiles\001225.out 001225.OUT"    "put c:\outfiles\001229.out 001229.OUT"    "put c:\outfiles\001234.out 001234.OUT"    "put c:\outfiles\001241.out 001241.OUT"    "put c:\outfiles\001244.out 001244.OUT"    "put c:\outfiles\001247.out 001247.OUT"    "put c:\outfiles\002001.out 002001.OUT"    "put c:\outfiles\002012.out 002012.OUT"    "put c:\outfiles\002013.out 002013.OUT"    "put c:\outfiles\002018.out 002018.OUT"    "put c:\outfiles\002025.out 002025.OUT"    "put c:\outfiles\002028.out 002028.OUT"    "put c:\outfiles\002036.out 002036.OUT"    "put c:\outfiles\002041.out 002041.OUT"    "put c:\outfiles\002045.out 002045.OUT"    "put c:\outfiles\002067.out 002067.OUT"    "put c:\outfiles\002072.out 002072.OUT"    "put c:\outfiles\002073.out 002073.OUT"    "put c:\outfiles\002088.out 002088.OUT"    "put c:\outfiles\002111.out 002111.OUT"    "put c:\outfiles\002112.out 002112.OUT"    "put c:\outfiles\002116.out 002116.OUT"    "put c:\outfiles\002146.out 002146.OUT"    "put c:\outfiles\002149.out 002149.OUT"    "put c:\outfiles\002150.out 002150.OUT"    "put c:\outfiles\002157.out 002157.OUT"    "put c:\outfiles\002158.out 002158.OUT"    "put c:\outfiles\002170.out 002170.OUT"    "put c:\outfiles\002174.out 002174.OUT"    "put c:\outfiles\002176.out 002176.OUT"    "put c:\outfiles\002181.out 002181.OUT"    "put c:\outfiles\002182.out 002182.OUT"    "put c:\outfiles\002183.out 002183.OUT"    "put c:\outfiles\002185.out 002185.OUT"    "put c:\outfiles\002196.out 002196.OUT"    "put c:\outfiles\002202.out 002202.OUT"    "put c:\outfiles\002203.out 002203.OUT"    "put c:\outfiles\002225.out 002225.OUT"    "put c:\outfiles\002234.out 002234.OUT"    "put c:\outfiles\002241.out 002241.OUT"    "put c:\outfiles\002244.out 002244.OUT"    "put c:\outfiles\002245.out 002245.OUT"    "put c:\outfiles\002247.out 002247.OUT"    "put c:\outfiles\003001.out 003001.OUT"    "put c:\outfiles\003013.out 003013.OUT"    "put c:\outfiles\003025.out 003025.OUT"    "put c:\outfiles\003028.out 003028.OUT"    "put c:\outfiles\003034.out 003034.OUT"    "put c:\outfiles\003045.out 003045.OUT"    "put c:\outfiles\003055.out 003055.OUT"    "put c:\outfiles\003073.out 003073.OUT"    "put c:\outfiles\003097.out 003097.OUT"    "put c:\outfiles\003116.out 003116.OUT"    "put c:\outfiles\003126.out 003126.OUT"    "put c:\outfiles\003146.out 003146.OUT"    "put c:\outfiles\003149.out 003149.OUT"    "put c:\outfiles\003150.out 003150.OUT"    "put c:\outfiles\003174.out 003174.OUT"    "put c:\outfiles\003176.out 003176.OUT"    "put c:\outfiles\003181

Searching for host...
Host "FTPINFO" does not exist.

B:\lws\1005>"put c:\outfiles\003182.out 003182.OUT"    "put c:\outfiles\003185.out 003185.OUT"    "put c:\outfiles\003203.out 003203.OUT"    "put c:\outfiles\003234.out 003234.OUT"    "put c:\outfiles\003241.out 003241.OUT"    "put c:\outfiles\003245.out 003245.OUT"    "put c:\outfiles\003247.out 003247.OUT"    "put c:\outfiles\003252.out 003252.OUT"    "put c:\outfiles\004001.out 004001.OUT"    "put c:\outfiles\004013.out 004013.OUT"    "put c:\outfiles\004016.out 004016.OUT"    "put c:\outfiles\004025.out 004025.OUT"    "put c:\outfiles\004028.out 004028.OUT"    "put c:\outfiles\004034.out 004034.OUT"    "put c:\outfiles\004036.out 004036.OUT"    "put c:\outfiles\004045.out 004045.OUT"    "put c:\outfiles\004067.out 004067.OUT"    "put c:\outfiles\004073.out 004073.OUT"    "put c:\outfiles\004111.out 004111.OUT"    "put c:\outfiles\004116.out 004116.OUT"    "put c:\outfiles\004126.out 004126.OUT"    "put c:\outfiles\004146.out 004146.OUT"    "put c:\outfiles\004149.out 004149.OUT"    "put c:\outfiles\004150.out 004150.OUT"    "put c:\outfiles\004170.out 004170.OUT"    "put c:\outfiles\004174.out 004174.OUT"    "put c:\outfiles\004176.out 004176.OUT"    "put c:\outfiles\004181.out 004181.OUT"    "put c:\outfiles\004182.out 004182.OUT"    "put c:\outfiles\004203.out 004203.OUT"    "put c:\outfiles\004229.out 004229.OUT"    "put c:\outfiles\004234.out 004234.OUT"    "put c:\outfiles\004241.out 004241.OUT"    "put c:\outfiles\004245.out 004245.OUT"    "put c:\outfiles\004247.out 004247.OUT"    "put c:\outfiles\005036.out 005036.OUT"    "put c:\outfiles\005100.out 005100.OUT"    "put c:\outfiles\005107.out 005107.OUT"    "put c:\outfiles\005146.out 005146.OUT"    "put c:\outfiles\005170.out 005170.OUT"    "put c:\outfiles\005182.out 005182.OUT"    "put c:\outfiles\005201.out 005201.OUT"    "put c:\outfiles\005245.out 005245.OUT"    "put c:\outfiles\006036.out 006036.OUT"    "put c:\outfiles\006146.out 006146.OUT"    "put c:\outfiles\011116.out 011116.OUT"    "put c:\outfiles\021116.out 021116.OUT"    "put c:\outfiles\034111.out 034111.OUT"    "put c:\outfiles\101018.out 101018.OUT"    "put c:\outfiles\101082.out 101082.OUT"    "put c:\outfiles\101134.out 101134.OUT"    "put c:\outfiles\101168.out 101168.OUT"    "put c:\outfiles\102072.out 102072.OUT"    "put c:\outfiles\102097.out 102097.OUT"    "put c:\outfiles\102112.out 102112.OUT"    "put c:\outfiles\102202.out 102202.OUT"    "put c:\outfiles\103034.out 103034.OUT"    "put c:\outfiles\103125.out 103125.OUT"    "put c:\outfiles\103181.out 103181.OUT"    "put c:\outfiles\103241.out 103241.OUT"    "put c:\outfiles\103247.out 103247.OUT"    "put c:\outfiles\104034.out 104034.OUT"    "put c:\outfiles\107070.out 107070.OUT"    "put c:\outfiles\120107.out 120107.OUT"    "open FTPINFO"     "put c:\outfiles\011178.out 011178.OUT"    "put c:\outfiles\012178.out 012178.OUT"    "put c:\outfiles\013178.out 013178.OUT"    "put c:\outfiles\021178.out 021178.OUT"    "put c:\outfiles\022178.out 022178.OUT"    "put c:\outfiles\003178.out 003178.OUT"    "put c:\outfiles\004178.out 004178.OUT"    "put c:\outfiles\051178.out 051178.OUT"    "put c:\outfiles\052178.out 052178.OUT"    "open FTPINFO"     "cd output"     "put c:\outfiles\101183.out 101183.out"    "put c:\outfiles\101209.out 101209.out"    "put c:\outfiles\105170.out 105170.out"    "put c:\outfiles\117057.out 117057.out"    "put c:\outfiles\196057.out 196057.out"    "open FTPINFO"     "put c:\outfiles\001220.out 001220.out"    "put c:\outfiles\002220.out 002220.out"    "put c:\outfiles\003220.out 003220.out"    "put c:\outfiles\004220.out 004220.out"    "put c:\outfiles\005220.out 005220.out"    "put c:\outfiles\006220.out 006220.out"    "put c:\outfiles\007220.out 007220.out"    "put c:\outfiles\008220.out 008220.out"    "put c:\outfiles\009220.out 009220.out"    "put c:\outfiles\013220.out 013220.out"    "put c:\outfiles\050220.out 050220.out"    "put c:\outfiles\051220.out 051220.out"    "put c:\outfiles\052220.out 052220.out"    "put c:\outfiles\053220.out 053220.out"    "put c:\outfiles\054220.out 054220.out"    "put c:\outfiles\055220.out 055220.out"    "put c:\outfiles\056220.out 056220.out"    "put c:\outfiles\057220.out 057220.out"    "put c:\outfiles\058220.out 058220.out"    "put c:\outfiles\059220.out 059220.out"    "open FTPINFO"     "cd out"    "put c:\outfiles\000001.out 000001.out"    "put c:\outfiles\000006.out 000006.out"    "put c:\outfiles\000013.out 000013.out"    "put c:\outfiles\000017.out 000017.out"    "put c:\outfiles\000035.out 000035.out"    "put c:\outfiles\000039.out 000039.out"    "put c:\outfiles\000044.out 000044.out"    "put c:\outfiles\000047.out 000047.out"    "put c:\outfiles\000050.out 000050.out"    "put c:\outfiles\000051.out 000051.out"    "put c:\outfiles\000052.out 000052.out"    "put c:\outfiles\000053.out 000053.out"    "put c:\outfiles\000056.out 000056.out"    "put c:\outfiles\000058.out 000058.out"    "put c:\outfiles\000060.out 000060.out"    "put c:\outfiles\000061.out 000061.out"    "put c:\outfiles\000064.out 000064.out"    "put c:\outfiles\000078.out 000078.out"    "put c:\outfiles\000079.out 000079.out"    "put c:\outfiles\000080.out 000080.out"    "put c:\outfiles\000084.out 000084.out"    "put c:\outfiles\000098.out 000098.out"    "put c:\outfiles\000103.out 000103.out"    "put c:\outfiles\000106.out 000106.out"    "put c:\outfiles\000118.out 000118.out"    "put c:\outfiles\000119.out 000119.out"    "put c:\outfiles\000120.out 000120.out"    "put c:\outfiles\000122.out 000122.out"    "put c:\outfiles\000127.out 000127.out"    "put c:\outfiles\000129.out 000129.out"    "put c:\outfiles\000134.out 000134.out"    "put c:\outfiles\000136.out 000136.out"    "put c:\outfiles\000151.out 000151.out"    "put c:\outfiles\000154.out 000154.out"    "put c:\outfiles\000155.out 000155.out"    "put c:\outfiles\000156.out 000156.out"    "put c:\outfiles\000157.out 000157.out"    "put c:\outfiles\000159.out 000159.out"    "put c:\outfiles\000167.out 000167.out"    "put c:\outfiles\000168.out 000168.out"    "put c:\outfiles\000177.out 000177.out"    "put c:\outfiles\000180.out 000180.out"    "put c:\outfiles\000189.out 000189.out"    "put c:\outfiles\000194.out 000194.out"    "put c:\outfiles\000196.out 000196.out"    "put c:\outfiles\000197.out 000197.out"    "put c:\outfiles\000201.out 000201.out"    "put c:\outfiles\000203.out 000203.out"    "put c:\outfiles\000206.out 000206.out"    "put c:\outfiles\000207.out 000207.out"    "put c:\outfiles\000209.out 000209.out"    "put c:\outfiles\000215.out 000215.out"    "put c:\outfiles\000216.out 000216.out"    "put c:\outfiles\000219.out 000219.out"    "put c:\outfiles\000220.out 000220.out"    "put c:\outfiles\000221.out 000221.out"    "put c:\outfiles\000224.out 000224.out"    "put c:\outfiles\000231.out 000231.out"    "put c:\outfiles\000239.out 000239.out"    "put c:\outfiles\000283.out 000283.out"    "put c:\outfiles\001001.out 001001.out"    "put c:\outfiles\001002.out 001002.out"    "put c:\outfiles\001003.out 001003.out"    "put c:\outfiles\001004.out 001004.out"    "put c:\outfiles\001005.out 001005.out"    "put c:\outfiles\001006.out 001006.out"    "put c:\outfiles\001007.out 001007.out"    "put c:\outfiles\001008.out 001008.out"    "put c:\outfiles\001009.out 001009.out"    "put c:\outfiles\001010.out 001010.out"    "put c:\outfiles\001011.out 001011.out"    "put c:\outfiles\001012.out 001012.out"    "put c:\outfiles\001016.out 001016.out"    "put c:\outfiles\001018.out 001018.out"    "put c:\outfiles\001021.out 001021.out"    "put c:\outfiles\001022.out 001022.out"    "put c:\outfiles\001023.out 001023.out"    "put c:\outfiles\001024.out 001024.out"    "put c:\outfiles\001025.out 001025.out"    "put c:\outfiles\001026.out 001026.out"    "put c:\outfiles\001027.out 001027.out"    "put c:\outfiles\001028.out 001028.out"    "put c:\outfiles\001029.out 001029.out"    "put c:\outfiles\001030.out 001030.out"    "put c:\outfiles\001033.out 001033.out"    "put c:\outfiles\001034.out 001034.out"    "put c:\outfiles\001036.out 001036.out"    "put c:\outfiles\001037.out 001037.out"    "put c:\outfiles\001038.out 001038.out"    "put c:\outfiles\001040.out 001040.out"    "put c:\outfiles\001041.out 001041.out"    "put c:\outfiles\001043.out 001043.out"    "put c:\outfiles\001045.out 001045.out"    "put c:\outfiles\001048.out 001048.out"    "put c:\outfiles\001050.out 001050.out"    "put c:\outfiles\001054.out 001054.out"    "put c:\outfiles\001055.out 001055.out"    "put c:\outfiles\001057.out 001057.out"    "put c:\outfiles\001059.out 001059.out"    "put c:\outfiles\001063.out 001063.out"    "put c:\ou
The filename, directory name, or volume label syntax is incorrect.

B:\lws\1005>"put c:\outfiles\001068.out 001068.out"    "put c:\outfiles\001069.out 001069.out"    "put c:\outfiles\001071.out 001071.out"    "put c:\outfiles\001072.out 001072.out"    "put c:\outfiles\001073.out 001073.out"    "put c:\outfiles\001075.out 001075.out"    "put c:\outfiles\001081.out 001081.out"    "put c:\outfiles\001082.out 001082.out"    "put c:\outfiles\001084.out 001084.out"    "put c:\outfiles\001085.out 001085.out"    "put c:\outfiles\001086.out 001086.out"    "put c:\outfiles\001088.out 001088.out"    "put c:\outfiles\001090.out 001090.out"    "put c:\outfiles\001091.out 001091.out"    "put c:\outfiles\001093.out 001093.out"    "put c:\outfiles\001097.out 001097.out"    "put c:\outfiles\001099.out 001099.out"    "put c:\outfiles\001100.out 001100.out"    "put c:\outfiles\001102.out 001102.out"    "put c:\outfiles\001107.out 001107.out"    "put c:\outfiles\001109.out 001109.out"    "put c:\outfiles\001110.out 001110.out"    "put c:\outfiles\001112.out 001112.out"    "put c:\outfiles\001113.out 001113.out"    "put c:\outfiles\001117.out 001117.out"    "put c:\outfiles\001121.out 001121.out"    "put c:\outfiles\001122.out 001122.out"    "put c:\outfiles\001124.out 001124.out"    "put c:\outfiles\001125.out 001125.out"    "put c:\outfiles\001126.out 001126.out"    "put c:\outfiles\001128.out 001128.out"    "put c:\outfiles\001130.out 001130.out"    "put c:\outfiles\001131.out 001131.out"    "put c:\outfiles\001133.out 001133.out"    "put c:\outfiles\001135.out 001135.out"    "put c:\outfiles\001137.out 001137.out"    "put c:\outfiles\001139.out 001139.out"    "put c:\outfiles\001141.out 001141.out"    "put c:\outfiles\001142.out 001142.out"    "put c:\outfiles\001143.out 001143.out"    "put c:\outfiles\001146.out 001146.out"    "put c:\outfiles\001147.out 001147.out"    "put c:\outfiles\001149.out 001149.out"    "put c:\outfiles\001150.out 001150.out"    "put c:\outfiles\001152.out 001152.out"    "put c:\outfiles\001153.out 001153.out"    "put c:\outfiles\001157.out 001157.out"    "put c:\outfiles\001158.out 001158.out"    "put c:\outfiles\001159.out 001159.out"    "put c:\outfiles\001161.out 001161.out"    "put c:\outfiles\001163.out 001163.out"    "put c:\outfiles\001164.out 001164.out"    "put c:\outfiles\001165.out 001165.out"    "put c:\outfiles\001166.out 001166.out"    "put c:\outfiles\001168.out 001168.out"    "put c:\outfiles\001169.out 001169.out"    "put c:\outfiles\001170.out 001170.out"    "put c:\outfiles\001171.out 001171.out"    "put c:\outfiles\001172.out 001172.out"    "put c:\outfiles\001173.out 001173.out"    "put c:\outfiles\001174.out 001174.out"    "put c:\outfiles\001175.out 001175.out"    "put c:\outfiles\001176.out 001176.out"    "put c:\outfiles\001179.out 001179.out"    "put c:\outfiles\001181.out 001181.out"    "put c:\outfiles\001182.out 001182.out"    "put c:\outfiles\001184.out 001184.out"    "put c:\outfiles\001185.out 001185.out"    "put c:\outfiles\001186.out 001186.out"    "put c:\outfiles\001187.out 001187.out"    "put c:\outfiles\001189.out 001189.out"    "put c:\outfiles\001190.out 001190.out"    "put c:\outfiles\001191.out 001191.out"    "put c:\outfiles\001192.out 001192.out"    "put c:\outfiles\001198.out 001198.out"    "put c:\outfiles\001199.out 001199.out"    "put c:\outfiles\001200.out 001200.out"    "put c:\outfiles\001202.out 001202.out"    "put c:\outfiles\001203.out 001203.out"    "put c:\outfiles\001204.out 001204.out"    "put c:\outfiles\001205.out 001205.out"    "put c:\outfiles\001208.out 001208.out"    "put c:\outfiles\001210.out 001210.out"    "put c:\outfiles\001212.out 001212.out"    "put c:\outfiles\001213.out 001213.out"    "put c:\outfiles\001218.out 001218.out"    "put c:\outfiles\001220.out 001220.out"    "put c:\outfiles\001221.out 001221.out"    "put c:\outfiles\001222.out 001222.out"    "put c:\outfiles\001223.out 001223.out"    "put c:\outfiles\001225.out 001225.out"    "put c:\outfiles\001226.out 001226.out"    "put c:\outfiles\001227.out 001227.out"    "put c:\outfiles\001228.out 001228.out"    "put c:\outfiles\001229.out 001229.out"    "put c:\outfiles\001230.out 001230.out"    "put c:\outfiles\001231.out 001231.out"    "put c:\outfiles\001232.out 001232.out"    "put c:\outfiles\001233.out 001233.out"    "put c:\outfiles\001234.out 001234.out"    "put c:\outfiles\001235.out 001235.out"    "put c:\outfiles\001236.out 001236.out"    "put c:\outfiles\001237.out 001237.out"    "put c:\outfiles\001238.out 001238.out"    "put c:\outfiles\001239.out 001239.out"    "put c:\outfiles\001241.out 001241.out"    "put c:\outfiles\001244.out 001244.out"    "put c:\outfiles\001246.out 001246.out"    "put c:\outfiles\001247.out 001247.out"    "put c:\outfiles\001248.out 001248.out"    "put c:\outfiles\001249.out 001249.out"    "put c:\outfiles\001250.out 001250.out"    "put c:\outfiles\001251.out 001251.out"    "put c:\outfiles\001252.out 001252.out"    "put c:\outfiles\001254.out 001254.out"    "put c:\outfiles\002001.out 002001.out"    "put c:\outfiles\002002.out 002002.out"    "put c:\outfiles\002003.out 002003.out"    "put c:\outfiles\002004.out 002004.out"    "put c:\outfiles\002005.out 002005.out"    "put c:\outfiles\002007.out 002007.out"    "put c:\outfiles\002008.out 002008.out"    "put c:\outfiles\002010.out 002010.out"    "put c:\outfiles\002011.out 002011.out"    "put c:\outfiles\002012.out 002012.out"    "put c:\outfiles\002013.out 002013.out"    "put c:\outfiles\002018.out 002018.out"    "put c:\outfiles\002019.out 002019.out"    "put c:\outfiles\002024.out 002024.out"    "put c:\outfiles\002025.out 002025.out"    "put c:\outfiles\002026.out 002026.out"    "put c:\outfiles\002027.out 002027.out"    "put c:\outfiles\002028.out 002028.out"    "put c:\outfiles\002029.out 002029.out"    "put c:\outfiles\002033.out 002033.out"    "put c:\outfiles\002036.out 002036.out"    "put c:\outfiles\002037.out 002037.out"    "put c:\outfiles\002041.out 002041.out"    "put c:\outfiles\002045.out 002045.out"    "put c:\outfiles\002048.out 002048.out"    "put c:\outfiles\002050.out 002050.out"    "put c:\outfiles\002057.out 002057.out"    "put c:\outfiles\002064.out 002064.out"    "put c:\outfiles\002065.out 002065.out"    "put c:\outfiles\002067.out 002067.out"    "put c:\outfiles\002068.out 002068.out"    "put c:\outfiles\002070.out 002070.out"    "put c:\outfiles\002071.out 002071.out"    "put c:\outfiles\002072.out 002072.out"    "put c:\outfiles\002073.out 002073.out"    "put c:\outfiles\002075.out 002075.out"    "put c:\outfiles\002079.out 002079.out"    "put c:\outfiles\002081.out 002081.out"    "put c:\outfiles\002082.out 002082.out"    "put c:\outfiles\002083.out 002083.out"    "put c:\outfiles\002084.out 002084.out"    "put c:\outfiles\002085.out 002085.out"    "put c:\outfiles\002088.out 002088.out"    "put c:\outfiles\002090.out 002090.out"    "put c:\outfiles\002091.out 002091.out"    "put c:\outfiles\002093.out 002093.out"    "put c:\outfiles\002100.out 002100.out"    "put c:\outfiles\002105.out 002105.out"    "put c:\outfiles\002107.out 002107.out"    "put c:\outfiles\002109.out 002109.out"    "put c:\outfiles\002110.out 002110.out"    "put c:\outfiles\002113.out 002113.out"    "put c:\outfiles\002114.out 002114.out"    "put c:\outfiles\002117.out 002117.out"    "put c:\outfiles\002121.out 002121.out"    "put c:\outfiles\002124.out 002124.out"    "put c:\outfiles\002126.out 002126.out"    "put c:\outfiles\002127.out 002127.out"    "put c:\outfiles\002128.out 002128.out"    "put c:\outfiles\002129.out 002129.out"    "put c:\outfiles\002130.out 002130.out"    "put c:\outfiles\002131.out 002131.out"    "put c:\outfiles\002133.out 002133.out"    "put c:\outfiles\002137.out 002137.out"    "put c:\outfiles\002142.out 002142.out"    "put c:\outfiles\002143.out 002143.out"    "put c:\outfiles\002144.out 002144.out"    "put c:\outfiles\002147.out 002147.out"    "put c:\outfiles\002150.out 002150.out"    "put c:\outfiles\002155.out 002155.out"    "put c:\outfiles\002158.out 002158.out"    "put c:\outfiles\002159.out 002159.out"    "put c:\outfiles\002161.out 002161.out"    "put c:\outfiles\002163.out 002163.out"    "put c:\outfiles\002165.out 002165.out"    "put c:\outfiles\002166.out 002166.out"    "put c:\outfiles\002169.out 002169.out"    "put c:\outfiles\002170.out 002170.out"    "put c:\outfiles\002172.out 002172.out"    "put c:\outfiles\002175.out 002175.out"    "put c:\outfiles\002176.out 002176.out"    "put c:\outfiles\002183.out 002183.out"    "put c:\outfiles\002184.out 002184.out"    "put c:\outfiles\002187.out 002187.out"    "put c:\outfiles\002196.out 002196.out"    "put c:\outfiles\002198.out 00
The filename, directory name, or volume label syntax is incorrect.

There seems to be a limit on command-length, see:

I assume the batch file is generated. So why don't you generate WinSCP script instead of a batch file?

Added. It's very simple, just a list of files to upload. There are definitely other methods for completing this, but I'd like to know why it fails midway through and seemingly removes a character from the directory.

Thanks for the log. Can you also post your script?

Log file is attached. The section we're looking at is:

* 2018-09-28 14:34:33.960 (EOSError) System Error. Code: 2.

* 2018-09-28 14:34:33.960 The system cannot find the file specified
. 2018-09-28 14:34:33.960 Asking user:
. 2018-09-28 14:34:33.960 File or folder 'c:\outfiles\00227.out' does not exist. ("System Error. Code: 2.

. 2018-09-28 14:34:33.960 The system cannot find the file specified")
< 2018-09-28 14:34:33.960 Script: File or folder 'c:\outfiles\00227.out' does not exist.
< 2018-09-28 14:34:33.960 Script: System Error. Code: 2.

< 2018-09-28 14:34:33.960 The system cannot find the file specified
* 2018-09-28 14:34:33.962 (ESkipFile) File or folder 'c:\outfiles\00227.out' does not exist.
* 2018-09-28 14:34:33.962 System Error. Code: 2.

That file name is not correctly being seen by scp, but it is CORRECT in the script. Previously, when it got to a certain point, it would remove the "s" character from the directory that it was attempting to upload files from, but some changes were made to formatting and now it's removing a character from the file name itself and then claiming that it's not found

Re: Error code 3 File not Found

Please attach a full session log file showing the problem (using the latest version of WinSCP).

To generate the session log file, use /log=path_to_log_file command-line argument. Submit the log with your post as an attachment. Note that passwords and passphrases not stored in the log. You may want to remove other data you consider sensitive though, such as host names, IP addresses, account names or file names (unless they are relevant to the problem). If you do not want to post the log publicly, you can mark the attachment as private.

Error code 3 File not Found

I know this has been a thing many folks have posted about but I'm running in to a rather strange issue I can't seem to understand.

< 2018-09-28 14:26:17.722 213 Modify=20180928133904; 002244.OUT
. 2018-09-28 14:26:17.722 Upload successful
. 2018-09-28 14:26:17.723 Transfer done: 'c:\outfiles\002244.out' => '/002244.OUT' [1069]
. 2018-09-28 14:26:17.723 Copying finished: Transferred: 1,069, Elapsed: 0:00:00, CPS: 0/s
> 2018-09-28 14:26:17.723 Script: put c:\outfiles\00225.out 002245.OUT
. 2018-09-28 14:26:17.724 Copying 1 files/directories to remote directory "/" - total size: 0
. 2018-09-28 14:26:17.724 PrTime: Yes; PrRO: No; Rght: rw-r--r--; PrR: No (No); FnCs: N; RIC: 0100; Resume: S (102400); CalcS: No; Mask: 002245.OUT
. 2018-09-28 14:26:17.724 TM: B; ClAr: No; RemEOF: No; RemBOM: No; CPS: 0; NewerOnly: No; InclM: ; ResumeL: 0
. 2018-09-28 14:26:17.724 AscM: *.*html; *.htm; *.txt; *.php; *.php3; *.cgi; *.c; *.cpp; *.h; *.pas; *.bas; *.tex; *.pl; *.js; .htaccess; *.xtml; *.css; *.cfg; *.ini; *.sh; *.xml
* 2018-09-28 14:26:17.726 (EOSError) System Error. Code: 2.

* 2018-09-28 14:26:17.726 The system cannot find the file specified
. 2018-09-28 14:26:17.727 Asking user:
. 2018-09-28 14:26:17.727 File or folder 'c:\outfiles\00225.out' does not exist. ("System Error. Code: 2.

. 2018-09-28 14:26:17.727 The system cannot find the file specified")
< 2018-09-28 14:26:17.727 Script: File or folder 'c:\outfiles\00225.out' does not exist.
< 2018-09-28 14:26:17.727 Script: System Error. Code: 2.

< 2018-09-28 14:26:17.727 The system cannot find the file specified
* 2018-09-28 14:26:17.729 (ESkipFile) File or folder 'c:\outfiles\00225.out' does not exist.
* 2018-09-28 14:26:17.729 System Error. Code: 2.
* 2018-09-28 14:26:17.729 The system cannot find the file specified

Now, the issue is, that's not the file name. The file name is 002245.out and it DOES exist. Previously, before I made some edits, scp was attempting to find c:\outfile\002245.out and that didn't exist either when it's specified in the script as 'outfiles'. is there some sort of formatting error here that's making SCP essentially cut a character from the path that we're using?