WebDav PUT File Fails With 409

Hello, I'm writing a custom application that imports/exports files from SharePoint 2010 using the WebDAV protocol. The application can handle most instances but is running into an issue when it attempts to upload a certain PDF file using the PUT request.

File uri path: /ip/IP Library/functional/comms/Communicating change research larkin.pdf

I have confirmed that the path /ip/IP Library/functional/comms/ already exists and and is accessible. Below is the 409 error code I keep receiving. It's quite frustrating and non-descript at least in the last couple of hours of Google searching.

Here is the CURL error output: 

HTTP/1.1 409 CONFLICT
Cache-Control: private,max-age=0
Content-Length: 0
Expires: Sun, 17 Mar 2013 19:45:29 GMT
Server: Microsoft-IIS/8.0
X-SharePointHealthScore: 0
x-irm-unknown-failure: notspirmencrypted
Public-Extension: http://schemas.microsoft.com/repl-2
X-MSDAVEXT_Error: 9895958; The%20PDF%20document%20you%20tried%20to%20upload%20was%20not%20encrypted%20in%20SharePoint%20therefore%20it%20cannot%20be%20uploaded%20to%20this%20library%2e
SPRequestGuid: ed940d9c-c2cb-402d-8afa-59484c656971
request-id: ed940d9c-c2cb-402d-8afa-59484c656971
X-FRAME-OPTIONS: SAMEORIGIN
SPRequestDuration: 1677
SPIisLatency: 0
Persistent-Auth: true
X-Powered-By: ASP.NET
MicrosoftSharePointTeamServices: 15.0.0.4420
X-Content-Type-Options: nosniff
X-MS-InvokeApp: 1; RequireReadOnly
Date: Mon, 01 Apr 2013 19:45:29 GMT

"
  ["headers":"Response":private]=>
  array(21) {
    ["Response Code"]=>
    int(409)
    ["Response Status"]=>
    string(8) "CONFLICT"
    ["Cache-Control"]=>
    string(17) "private,max-age=0"
    ["Content-Length"]=>
    string(1) "0"
    ["Expires"]=>
    string(29) "Sun, 17 Mar 2013 19:45:29 GMT"
    ["Server"]=>
    string(17) "Microsoft-IIS/8.0"
    ["X-Sharepointhealthscore"]=>
    string(1) "0"
    ["X-Irm-Unknown-Failure"]=>
    string(17) "notspirmencrypted"
    ["Public-Extension"]=>
    string(35) "http://schemas.microsoft.com/repl-2"
    ["X-Msdavext-Error"]=>
    string(166) "9895958; The%20PDF%20document%20you%20tried%20to%20upload%20was%20not%20encrypted%20in%20SharePoint%20therefore%20it%20cannot%20be%20uploaded%20to%20this%20library%2e"
    ["Sprequestguid"]=>
    string(36) "ed940d9c-c2cb-402d-8afa-59484c656971"
    ["Request-Id"]=>
    string(36) "ed940d9c-c2cb-402d-8afa-59484c656971"
    ["X-Frame-Options"]=>
    string(10) "SAMEORIGIN"
    ["Sprequestduration"]=>
    string(4) "1677"
    ["Spiislatency"]=>
    string(1) "0"
    ["Persistent-Auth"]=>
    string(4) "true"
    ["X-Powered-By"]=>
    string(7) "ASP.NET"
    ["Microsoftsharepointteamservices"]=>
    string(11) "15.0.0.4420"
    ["X-Content-Type-Options"]=>
    string(7) "nosniff"
    ["X-Ms-Invokeapp"]=>
    string(18) "1; RequireReadOnly"
    ["Date"]=>
    string(29) "Mon, 01 Apr 2013 19:45:29 GMT"
  }
  ["http_code":"Response":private]=>
  int(409)
  ["json":"Response":private]=>
  NULL
  ["error":"Response":private]=>
  NULL
}

Any advice would be greatly appreciated!