mkdir commands not sent when necessary

Using SFTP, I'm trying to upload a folder into a Drupal hosting platform (Pantheon) and SmartFTP is not playing nicely with this particular server, or vice versa. Essentially, files won't upload unless the directory that's supposed to contain them already exists.
 
For example, I dragged a folder called "ctools" from the local window to the remote window and the files were added to the transfer queue, and then all of the files in the queue fail to upload. Here's the log from the first file in the list, which should have ended up in code/sites/all/modules/contrib/ctools ... but it fails becuase ctools/ doesn't exist yet:
[16:52:14] Operation Begin
[16:52:14] Resolving path "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites/all/modules/contrib/ctools".
[16:52:14] Path successfully resolved to "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites/all/modules/contrib/ctools".
[16:52:14] Getting properties (Date modified, Size) of "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites/all/modules/contrib/ctools/API.txt"
[16:52:14] Getting attributes of "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites/all/modules/contrib/ctools/API.txt".
[16:52:14] 2 No such file or directory
[16:52:14] Uploading file to "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites/all/modules/contrib/ctools/API.txt".
[16:52:14] StartPosition=0, EndPosition=0.
[16:52:14] 2 No such file or directory
[16:52:14] Transfer failed.
[16:52:14] Operation End
Normally SmartFTP would have sent a mkdir command to create ctools/, but in this case it didn't.
 
If I manually create ctools/, the transfer queue will upload things fine ... until the queue reaches files in a subdirectory of ctools/, such as ctools/css/button.css — again, because SmartFTP doesn't create the css/ directory, the file transfer fails.
 
I'm not convinced this is a server configuration issue because I was able to upload the entire ctools/ folder using FileZilla by doing the same kind of drag-and-drop action from local to remote. On the other hand, this is the only time I've ever seen SmartFTP have this problem uploading files to a server using SFTP.
 
Here's relevant system info:
+- System -----------------------------
Name                : Microsoft® Windows Vista™ Home Premium 
Version             : 6.0.6002 Service Pack 2
CPU Speed           : 2210 MHz
Architecture        : x86
Total Memory        : 3069 MB
Free Memory         :  827 MB
UserName            : [redacted]
Machine Id          : [redacted]

+- SmartFTP ---------------------------
Version             : 5.0.1364.0
Time Stamp          : 2015-04-15 05:40:24
Platform            : x86
Id                  : [redacted]
License Id          : [redacted]
Maintenance         : 2016-11-20T00:00:00
Days in use         : 2471

+- Language ---------------------------
en-US

Here's the intial connection log:
[16:49:11] SmartFTP v5.0.1364.0
[16:49:11] Resolving host name "appserver.dev.fbed5b95-fb7c-4d5e-a7be-030baf7c87a6.drush.in"
[16:49:11] Connecting to 23.253.170.215 Port: 2222
[16:49:11] Connected to appserver.dev.fbed5b95-fb7c-4d5e-a7be-030baf7c87a6.drush.in.
[16:49:11] SSH protocol version reply. Client Id: SSH-2.0-SmartFTP
[16:49:12] SSH-2.0-Twisted
[16:49:12] Starting SSH session. Remote Id: "SSH-2.0-Twisted"
[16:49:12] Server Algorithm Suite
           Key Exchange: diffie-hellman-group1-sha1
           Server Host Key: ssh-rsa
           Client to Server Encryption: aes256-ctr,aes256-cbc,aes192-ctr,aes192-cbc,aes128-ctr,aes128-cbc,cast128-ctr,cast128-cbc,blowfish-ctr,blowfish-cbc,3des-ctr,3des-cbc
           Server to Client Encryption: aes256-ctr,aes256-cbc,aes192-ctr,aes192-cbc,aes128-ctr,aes128-cbc,cast128-ctr,cast128-cbc,blowfish-ctr,blowfish-cbc,3des-ctr,3des-cbc
           Client to Server HMAC: hmac-sha1,hmac-md5
           Server to Client HMAC: hmac-sha1,hmac-md5
           Client to Server Compression: none,zlib
           Server to Client Compression: none,zlib
[16:49:12] Selected Algorithm Suite
           Key Exchange: diffie-hellman-group1-sha1
           Server Host Key: ssh-rsa
           Client to Server Encryption: aes256-ctr
           Server to Client Encryption: aes256-ctr
           Client to Server HMAC: hmac-sha1
           Server to Client HMAC: hmac-sha1
           Client to Server Compression: zlib
           Server to Client Compression: zlib
[16:49:12] Client Algorithm Suite
           Key Exchange: curve25519-sha256@libssh.org,ecdh-sha2-nistp256,ecdh-sha2-nistp384,ecdh-sha2-nistp521,diffie-hellman-group-exchange-sha256,diffie-hellman-group-exchange-sha1,diffie-hellman-group1-sha1,diffie-hellman-group14-sha1,rsa1024-sha1
           Server Host Key: ecdsa-sha2-nistp256,ecdsa-sha2-nistp384,ecdsa-sha2-nistp521,x509v3-sign-rsa-sha1,x509v3-sign-dss-sha1,ssh-rsa,ssh-dss
           Client to Server Encryption: aes128-gcm@openssh.com,aes256-gcm@openssh.com,aes256-ctr,aes256-cbc,rijndael256-cbc,rijndael-cbc@lysator.liu.se,aes192-ctr,aes128-ctr,3des-cbc,blowfish-cbc,cast128-cbc,aes128-cbc,rijndael128-cbc,aes192-cbc,rijndael192-cbc
           Server to Client Encryption: aes128-gcm@openssh.com,aes256-gcm@openssh.com,aes256-ctr,aes256-cbc,rijndael256-cbc,rijndael-cbc@lysator.liu.se,aes192-ctr,aes128-ctr,3des-cbc,blowfish-cbc,cast128-cbc,aes128-cbc,rijndael128-cbc,aes192-cbc,rijndael192-cbc
           Client to Server HMAC: hmac-sha2-512,hmac-sha2-256,hmac-sha1,hmac-md5
           Server to Client HMAC: hmac-sha2-512,hmac-sha2-256,hmac-sha1,hmac-md5
           Client to Server Compression: zlib@openssh.com,zlib,none
           Server to Client Compression: zlib@openssh.com,zlib,none
[16:49:12] Key Exchange Algorithm: diffie-hellman-group1-sha1
[16:49:13] Server "ssh-rsa" host key fingerprint: B5:EA:23:EB:7B:7B:0D:17:C7:13:47:92:EA:70:C1:B5
[16:49:13] Key exchange completed.
[16:49:13] Requesting service "ssh-userauth".
[16:49:13] RTT: 96.761 ms
[16:49:13] Authentication request. Method: none
[16:49:13] Server supported authentications: password,publickey
[16:49:13] Authentication request. Method: password
[16:49:13] User authentication successful.
[16:49:13] SSH session established.
[16:49:13] Opening channel 0.
[16:49:13] Channel successfully opened (Local=0, Remote=0).
[16:49:13] Requesting subystem "sftp" (Local=0, Remote=0).
[16:49:13] Sending FXP initialization. Protocol version=6.
[16:49:13] SFTP protocol version 3
[16:49:13] Resolving path ".".
[16:49:13] Path successfully resolved to "/srv/bindings/7168c07ee21e474d877da90805e1b0a0".
[16:49:13] Resolving path "/srv/bindings/7168c07ee21e474d877da90805e1b0a0".
[16:49:13] Path successfully resolved to "/srv/bindings/7168c07ee21e474d877da90805e1b0a0".
[16:49:13] Reading directory "/srv/bindings/7168c07ee21e474d877da90805e1b0a0".
[16:49:13] 3145 bytes transferred. (43.8 KB/s) (70 ms)
[16:49:13] Closing file handle.
[16:49:13] Directory listing complete.
[16:49:13] Getting attributes of "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/php".
[16:49:13] Attributes successfully obtained.
[16:49:13] Getting attributes of "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/drush".
[16:49:13] Attributes successfully obtained.
[16:49:15] Resolving path "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code".
[16:49:15] Path successfully resolved to "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code".
[16:49:15] Reading directory "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code".
[16:49:15] 3399 bytes transferred. (55.3 KB/s) (60 ms)
[16:49:15] Closing file handle.
[16:49:15] Directory listing complete.
[16:49:43] Resolving path "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites".
[16:49:43] Path successfully resolved to "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites".
[16:49:43] Reading directory "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites".
[16:49:43] 467 bytes transferred. (8.60 KB/s) (53 ms)
[16:49:43] Closing file handle.
[16:49:43] Directory listing complete.
[16:49:43] Resolving path "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites/all".
[16:49:43] Path successfully resolved to "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites/all".
[16:49:43] Reading directory "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites/all".
[16:49:43] 227 bytes transferred. (4.18 KB/s) (53 ms)
[16:49:43] Closing file handle.
[16:49:43] Directory listing complete.
[16:51:11] Resolving path "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites/all/modules".
[16:51:11] Path successfully resolved to "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites/all/modules".
[16:51:11] Reading directory "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites/all/modules".
[16:51:11] 455 bytes transferred. (5.62 KB/s) (79 ms)
[16:51:11] Closing file handle.
[16:51:11] Directory listing complete.
[16:51:13] Resolving path "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites/all/modules/contrib".
[16:51:13] Path successfully resolved to "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites/all/modules/contrib".
[16:51:13] Reading directory "/srv/bindings/7168c07ee21e474d877da90805e1b0a0/code/sites/all/modules/contrib".
[16:51:13] 221 bytes transferred. (4.23 KB/s) (51 ms)
[16:51:13] Closing file handle.
[16:51:13] Directory listing complete.
[16:51:38] The operation has been added to the Transfer Queue. Check the Transfer Queue for the status.
[16:52:14] The operation has been added to the Transfer Queue. Check the Transfer Queue for the status.
[17:01:13] Server closed connection