diff --git a/.travis.yml b/.travis.yml
index 7a7cfb2f9b4..7012f369a8a 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -22,7 +22,7 @@ env:
 matrix:
   include:
     - os: windows
-      env: OPT=Debug BRANCH=master
+      env: OPT=Debug BRANCH=master UPLOAD_ID=vs-debug
 
     - os: windows
       env: OPT=Release BRANCH=master
diff --git a/utils/travis/steps/install.sh b/utils/travis/steps/install.sh
index 7b12842c873..6bb5f888fa5 100755
--- a/utils/travis/steps/install.sh
+++ b/utils/travis/steps/install.sh
@@ -38,7 +38,8 @@ elif [ "$TRAVIS_OS_NAME" = "windows" ]; then
     7z x VC15.zip
     mv external-VC15 external
     cd $start
-    export PATH="/c/Python36:"$PATH":/c/Program Files (x86)/Microsoft Visual Studio/2017/BuildTools/MSBuild/15.0/Bin/amd64:$start/../external/dll"
+    export PATH="/c/Python36:"$PATH":/c/Program Files (x86)/Microsoft Visual Studio/2017/BuildTools/MSBuild/15.0/Bin/amd64:$start/../external/dll:/c/Python36/Scripts/"
+    yes | pip3 install paramiko
     if [ "$(which python3)" == "" ] || [ "$(which sqlite3)" == "" ] || [ ! -d "../external" ]; then
         echo "Failed to retrieve dependencies!"
         exit 1
diff --git a/utils/travis/steps/script.sh b/utils/travis/steps/script.sh
index 21e95a5085e..00f0dec8c04 100755
--- a/utils/travis/steps/script.sh
+++ b/utils/travis/steps/script.sh
@@ -43,6 +43,10 @@ elif [ "$TRAVIS_OS_NAME" = "windows" ]; then
     powershell "MSBuild.exe projectfiles/VC14/wesnoth.sln -p:PlatformToolset=v141 -p:Configuration=$OPT"
     BUILD_RET=$?
 
+    if [ "$UPLOAD_ID" != "" ] && [ "$TRAVIS_PULL_REQUEST" == "false" ]; then
+        ./utils/travis/sftp wesnoth.exe wesnothd.exe
+    fi
+
     if [ "$BUILD_RET" != "0" ]; then
         sqlite3 "projectfiles/VC14/$OPT/filehashes.sqlite" "update FILES set MD5 = OLD_MD5, OLD_MD5 = '-' where OLD_MD5 != '-'"
     else