diff --git a/plugins/guests/darwin/cap/shell_expand_guest_path.rb b/plugins/guests/darwin/cap/shell_expand_guest_path.rb
index 1fdcf5215..22c7bd11a 100644
--- a/plugins/guests/darwin/cap/shell_expand_guest_path.rb
+++ b/plugins/guests/darwin/cap/shell_expand_guest_path.rb
@@ -4,7 +4,7 @@ module VagrantPlugins
       class ShellExpandGuestPath
         def self.shell_expand_guest_path(machine, path)
           real_path = nil
-          machine.communicate.execute("printf #{path}") do |type, data|
+          machine.communicate.execute("printf \"#{path}\"") do |type, data|
             if type == :stdout
               real_path ||= ""
               real_path += data
@@ -14,7 +14,7 @@ module VagrantPlugins
           if !real_path
             # If no real guest path was detected, this is really strange
             # and we raise an exception because this is a bug.
-            raise ShellExpandFailed
+            raise Vagrant::Errors::ShellExpandFailed
           end
 
           # Chomp the string so that any trailing newlines are killed
diff --git a/plugins/guests/freebsd/cap/shell_expand_guest_path.rb b/plugins/guests/freebsd/cap/shell_expand_guest_path.rb
index 6d2f6e16a..14ae7184d 100644
--- a/plugins/guests/freebsd/cap/shell_expand_guest_path.rb
+++ b/plugins/guests/freebsd/cap/shell_expand_guest_path.rb
@@ -4,7 +4,7 @@ module VagrantPlugins
       class ShellExpandGuestPath
         def self.shell_expand_guest_path(machine, path)
           real_path = nil
-          machine.communicate.execute("printf #{path}",
+          machine.communicate.execute("printf \"#{path}\"",
                                       shell: "sh") do |type, data|
             if type == :stdout
               real_path ||= ""
@@ -15,7 +15,7 @@ module VagrantPlugins
           if !real_path
             # If no real guest path was detected, this is really strange
             # and we raise an exception because this is a bug.
-            raise ShellExpandFailed
+            raise Vagrant::Errors::ShellExpandFailed
           end
 
           # Chomp the string so that any trailing newlines are killed
diff --git a/plugins/guests/linux/cap/shell_expand_guest_path.rb b/plugins/guests/linux/cap/shell_expand_guest_path.rb
index cc32d7f7c..653068a78 100644
--- a/plugins/guests/linux/cap/shell_expand_guest_path.rb
+++ b/plugins/guests/linux/cap/shell_expand_guest_path.rb
@@ -4,7 +4,7 @@ module VagrantPlugins
       class ShellExpandGuestPath
         def self.shell_expand_guest_path(machine, path)
           real_path = nil
-          machine.communicate.execute("echo; printf #{path}") do |type, data|
+          machine.communicate.execute("echo; printf \"#{path}\"") do |type, data|
             if type == :stdout
               real_path ||= ""
               real_path += data
@@ -19,7 +19,7 @@ module VagrantPlugins
           if !real_path
             # If no real guest path was detected, this is really strange
             # and we raise an exception because this is a bug.
-            raise ShellExpandFailed
+            raise Vagrant::Errors::ShellExpandFailed
           end
 
           # Chomp the string so that any trailing newlines are killed
diff --git a/plugins/guests/netbsd/cap/shell_expand_guest_path.rb b/plugins/guests/netbsd/cap/shell_expand_guest_path.rb
index 8471f4724..007c5f944 100644
--- a/plugins/guests/netbsd/cap/shell_expand_guest_path.rb
+++ b/plugins/guests/netbsd/cap/shell_expand_guest_path.rb
@@ -4,7 +4,7 @@ module VagrantPlugins
       class ShellExpandGuestPath
         def self.shell_expand_guest_path(machine, path)
           real_path = nil
-          machine.communicate.execute("printf #{path}") do |type, data|
+          machine.communicate.execute("printf \"#{path}\"") do |type, data|
             if type == :stdout
               real_path ||= ""
               real_path += data
@@ -14,7 +14,7 @@ module VagrantPlugins
           if !real_path
             # If no real guest path was detected, this is really strange
             # and we raise an exception because this is a bug.
-            raise ShellExpandFailed
+            raise Vagrant::Errors::ShellExpandFailed
           end
 
           # Chomp the string so that any trailing newlines are killed
diff --git a/plugins/guests/openbsd/cap/shell_expand_guest_path.rb b/plugins/guests/openbsd/cap/shell_expand_guest_path.rb
index 653493548..2a4f8b5ed 100644
--- a/plugins/guests/openbsd/cap/shell_expand_guest_path.rb
+++ b/plugins/guests/openbsd/cap/shell_expand_guest_path.rb
@@ -4,7 +4,7 @@ module VagrantPlugins
       class ShellExpandGuestPath
         def self.shell_expand_guest_path(machine, path)
           real_path = nil
-          machine.communicate.execute("printf #{path}") do |type, data|
+          machine.communicate.execute("printf \"#{path}\"") do |type, data|
             if type == :stdout
               real_path ||= ""
               real_path += data
@@ -14,7 +14,7 @@ module VagrantPlugins
           if !real_path
             # If no real guest path was detected, this is really strange
             # and we raise an exception because this is a bug.
-            raise ShellExpandFailed
+            raise Vagrant::Errors::ShellExpandFailed
           end
 
           # Chomp the string so that any trailing newlines are killed
diff --git a/plugins/provisioners/file/provisioner.rb b/plugins/provisioners/file/provisioner.rb
index 7b997a7dc..46355c11b 100644
--- a/plugins/provisioners/file/provisioner.rb
+++ b/plugins/provisioners/file/provisioner.rb
@@ -3,14 +3,30 @@ module VagrantPlugins
     class Provisioner < Vagrant.plugin("2", :provisioner)
       def provision
         @machine.communicate.tap do |comm|
+          source = File.expand_path(config.source)
           destination = expand_guest_path(config.destination)
 
+          # if source is a directory, make it then trim destination with dirname
           # Make sure the remote path exists
-          command = "mkdir -p %s" % File.dirname(destination)
+          if File.directory?(source)
+            # We need to make sure the actual destination folder
+            # also exists before uploading, otherwise
+            # you will get nested folders. We also need to append
+            # a './' to the source folder so we copy the contents
+            # rather than the folder itself, in case a users destination
+            # folder differs from its source.
+            #
+            # https://serverfault.com/questions/538368/make-scp-always-overwrite-or-create-directory
+            # https://unix.stackexchange.com/questions/292641/get-scp-path-behave-like-rsync-path/292732
+            command = "mkdir -p \"%s\"" % destination
+            source << "/."
+          else
+            command = "mkdir -p \"%s\"" % File.dirname(destination)
+          end
           comm.execute(command)
 
           # now upload the file
-          comm.upload(File.expand_path(config.source), destination)
+          comm.upload(source, destination)
         end
       end
 
diff --git a/test/unit/plugins/guests/darwin/cap/shell_expand_guest_path_test.rb b/test/unit/plugins/guests/darwin/cap/shell_expand_guest_path_test.rb
new file mode 100644
index 000000000..fbbc45588
--- /dev/null
+++ b/test/unit/plugins/guests/darwin/cap/shell_expand_guest_path_test.rb
@@ -0,0 +1,43 @@
+require_relative "../../../../base"
+
+describe "VagrantPlugins::GuestDarwin::Cap::ShellExpandGuestPath" do
+  let(:caps) do
+    VagrantPlugins::GuestDarwin::Plugin
+      .components
+      .guest_capabilities[:darwin]
+  end
+
+  let(:machine) { double("machine") }
+  let(:comm) { VagrantTests::DummyCommunicator::Communicator.new(machine) }
+
+  before do
+    allow(machine).to receive(:communicate).and_return(comm)
+  end
+
+  describe "#shell_expand_guest_path" do
+    let(:cap) { caps.get(:shell_expand_guest_path) }
+
+    it "expands the path" do
+      path = "/home/vagrant/folder"
+      allow(machine.communicate).to receive(:execute).
+        with(any_args).and_yield(:stdout, "/home/vagrant/folder")
+
+      cap.shell_expand_guest_path(machine, path)
+    end
+
+    it "raises an exception if no path was detected" do
+      path = "/home/vagrant/folder"
+      expect { cap.shell_expand_guest_path(machine, path) }.
+        to raise_error(Vagrant::Errors::ShellExpandFailed)
+    end
+
+    it "returns a path with a space in it" do
+      path = "/home/vagrant folder/folder"
+      allow(machine.communicate).to receive(:execute).
+        with(any_args).and_yield(:stdout, "/home/vagrant folder/folder")
+
+      expect(machine.communicate).to receive(:execute).with("printf \"#{path}\"")
+      cap.shell_expand_guest_path(machine, path)
+    end
+  end
+end
diff --git a/test/unit/plugins/guests/freebsd/cap/shell_expand_guest_path_test.rb b/test/unit/plugins/guests/freebsd/cap/shell_expand_guest_path_test.rb
new file mode 100644
index 000000000..2f10f8663
--- /dev/null
+++ b/test/unit/plugins/guests/freebsd/cap/shell_expand_guest_path_test.rb
@@ -0,0 +1,44 @@
+require_relative "../../../../base"
+
+describe "VagrantPlugins::GuestFreeBSD::Cap::ShellExpandGuestPath" do
+  let(:caps) do
+    VagrantPlugins::GuestFreeBSD::Plugin
+      .components
+      .guest_capabilities[:freebsd]
+  end
+
+  let(:machine) { double("machine") }
+  let(:comm) { VagrantTests::DummyCommunicator::Communicator.new(machine) }
+
+  before do
+    allow(machine).to receive(:communicate).and_return(comm)
+  end
+
+  describe "#shell_expand_guest_path" do
+    let(:cap) { caps.get(:shell_expand_guest_path) }
+
+    it "expands the path" do
+      path = "/home/vagrant/folder"
+      allow(machine.communicate).to receive(:execute).
+        with(any_args).and_yield(:stdout, "/home/vagrant/folder")
+
+      cap.shell_expand_guest_path(machine, path)
+    end
+
+    it "raises an exception if no path was detected" do
+      path = "/home/vagrant/folder"
+      expect { cap.shell_expand_guest_path(machine, path) }.
+        to raise_error(Vagrant::Errors::ShellExpandFailed)
+    end
+
+    it "returns a path with a space in it" do
+      path = "/home/vagrant folder/folder"
+      allow(machine.communicate).to receive(:execute).
+        with(any_args).and_yield(:stdout, "/home/vagrant folder/folder")
+
+      expect(machine.communicate).to receive(:execute)
+        .with("printf \"#{path}\"", {:shell=>"sh"})
+      cap.shell_expand_guest_path(machine, path)
+    end
+  end
+end
diff --git a/test/unit/plugins/guests/linux/cap/shell_expand_guest_path_test.rb b/test/unit/plugins/guests/linux/cap/shell_expand_guest_path_test.rb
new file mode 100644
index 000000000..0caf4ae1d
--- /dev/null
+++ b/test/unit/plugins/guests/linux/cap/shell_expand_guest_path_test.rb
@@ -0,0 +1,43 @@
+require_relative "../../../../base"
+
+describe "VagrantPlugins::GuestLinux::Cap::ShellExpandGuestPath" do
+  let(:caps) do
+    VagrantPlugins::GuestLinux::Plugin
+      .components
+      .guest_capabilities[:linux]
+  end
+
+  let(:machine) { double("machine") }
+  let(:comm) { VagrantTests::DummyCommunicator::Communicator.new(machine) }
+
+  before do
+    allow(machine).to receive(:communicate).and_return(comm)
+  end
+
+  describe "#shell_expand_guest_path" do
+    let(:cap) { caps.get(:shell_expand_guest_path) }
+
+    it "expands the path" do
+      path = "/home/vagrant/folder"
+      allow(machine.communicate).to receive(:execute).
+        with(any_args).and_yield(:stdout, "/home/vagrant/folder")
+
+      cap.shell_expand_guest_path(machine, path)
+    end
+
+    it "raises an exception if no path was detected" do
+      path = "/home/vagrant/folder"
+      expect { cap.shell_expand_guest_path(machine, path) }.
+        to raise_error(Vagrant::Errors::ShellExpandFailed)
+    end
+
+    it "returns a path with a space in it" do
+      path = "/home/vagrant folder/folder"
+      allow(machine.communicate).to receive(:execute).
+        with(any_args).and_yield(:stdout, "/home/vagrant folder/folder")
+
+      expect(machine.communicate).to receive(:execute).with("echo; printf \"#{path}\"")
+      cap.shell_expand_guest_path(machine, path)
+    end
+  end
+end
diff --git a/test/unit/plugins/guests/netbsd/cap/shell_expand_guest_path_test.rb b/test/unit/plugins/guests/netbsd/cap/shell_expand_guest_path_test.rb
new file mode 100644
index 000000000..49e4e6305
--- /dev/null
+++ b/test/unit/plugins/guests/netbsd/cap/shell_expand_guest_path_test.rb
@@ -0,0 +1,43 @@
+require_relative "../../../../base"
+
+describe "VagrantPlugins::GuestNetBSD::Cap::ShellExpandGuestPath" do
+  let(:caps) do
+    VagrantPlugins::GuestNetBSD::Plugin
+      .components
+      .guest_capabilities[:netbsd]
+  end
+
+  let(:machine) { double("machine") }
+  let(:comm) { VagrantTests::DummyCommunicator::Communicator.new(machine) }
+
+  before do
+    allow(machine).to receive(:communicate).and_return(comm)
+  end
+
+  describe "#shell_expand_guest_path" do
+    let(:cap) { caps.get(:shell_expand_guest_path) }
+
+    it "expands the path" do
+      path = "/home/vagrant/folder"
+      allow(machine.communicate).to receive(:execute).
+        with(any_args).and_yield(:stdout, "/home/vagrant/folder")
+
+      cap.shell_expand_guest_path(machine, path)
+    end
+
+    it "raises an exception if no path was detected" do
+      path = "/home/vagrant/folder"
+      expect { cap.shell_expand_guest_path(machine, path) }.
+        to raise_error(Vagrant::Errors::ShellExpandFailed)
+    end
+
+    it "returns a path with a space in it" do
+      path = "/home/vagrant folder/folder"
+      allow(machine.communicate).to receive(:execute).
+        with(any_args).and_yield(:stdout, "/home/vagrant folder/folder")
+
+      expect(machine.communicate).to receive(:execute).with("printf \"#{path}\"")
+      cap.shell_expand_guest_path(machine, path)
+    end
+  end
+end
diff --git a/test/unit/plugins/guests/openbsd/cap/shell_expand_guest_path_test.rb b/test/unit/plugins/guests/openbsd/cap/shell_expand_guest_path_test.rb
new file mode 100644
index 000000000..1cd787911
--- /dev/null
+++ b/test/unit/plugins/guests/openbsd/cap/shell_expand_guest_path_test.rb
@@ -0,0 +1,43 @@
+require_relative "../../../../base"
+
+describe "VagrantPlugins::GuestOpenBSD::Cap::ShellExpandGuestPath" do
+  let(:caps) do
+    VagrantPlugins::GuestOpenBSD::Plugin
+      .components
+      .guest_capabilities[:openbsd]
+  end
+
+  let(:machine) { double("machine") }
+  let(:comm) { VagrantTests::DummyCommunicator::Communicator.new(machine) }
+
+  before do
+    allow(machine).to receive(:communicate).and_return(comm)
+  end
+
+  describe "#shell_expand_guest_path" do
+    let(:cap) { caps.get(:shell_expand_guest_path) }
+
+    it "expands the path" do
+      path = "/home/vagrant/folder"
+      allow(machine.communicate).to receive(:execute).
+        with(any_args).and_yield(:stdout, "/home/vagrant/folder")
+
+      cap.shell_expand_guest_path(machine, path)
+    end
+
+    it "raises an exception if no path was detected" do
+      path = "/home/vagrant/folder"
+      expect { cap.shell_expand_guest_path(machine, path) }.
+        to raise_error(Vagrant::Errors::ShellExpandFailed)
+    end
+
+    it "returns a path with a space in it" do
+      path = "/home/vagrant folder/folder"
+      allow(machine.communicate).to receive(:execute).
+        with(any_args).and_yield(:stdout, "/home/vagrant folder/folder")
+
+      expect(machine.communicate).to receive(:execute).with("printf \"#{path}\"")
+      cap.shell_expand_guest_path(machine, path)
+    end
+  end
+end
diff --git a/test/unit/plugins/provisioners/file/provisioner_test.rb b/test/unit/plugins/provisioners/file/provisioner_test.rb
index a42f1169c..8da38e6d7 100644
--- a/test/unit/plugins/provisioners/file/provisioner_test.rb
+++ b/test/unit/plugins/provisioners/file/provisioner_test.rb
@@ -34,7 +34,25 @@ describe VagrantPlugins::FileUpload::Provisioner do
       allow(config).to receive(:source).and_return("/source")
       allow(config).to receive(:destination).and_return("/foo/bar")
 
-      expect(communicator).to receive(:execute).with("mkdir -p /foo")
+      expect(communicator).to receive(:execute).with("mkdir -p \"/foo\"")
+
+      subject.provision
+    end
+
+    it "creates the destination directory with a space" do
+      allow(config).to receive(:source).and_return("/source")
+      allow(config).to receive(:destination).and_return("/foo bar/bar")
+
+      expect(communicator).to receive(:execute).with("mkdir -p \"/foo bar\"")
+
+      subject.provision
+    end
+
+    it "creates the destination directory above file" do
+      allow(config).to receive(:source).and_return("/source/file.sh")
+      allow(config).to receive(:destination).and_return("/foo/bar/file.sh")
+
+      expect(communicator).to receive(:execute).with("mkdir -p \"/foo/bar\"")
 
       subject.provision
     end