diff --git a/plugins/guests/darwin/cap/shell_expand_guest_path.rb b/plugins/guests/darwin/cap/shell_expand_guest_path.rb
index 1fdcf5215..3bf439ef9 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
diff --git a/plugins/guests/freebsd/cap/shell_expand_guest_path.rb b/plugins/guests/freebsd/cap/shell_expand_guest_path.rb
index 6d2f6e16a..854a2eef8 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 ||= ""
diff --git a/plugins/guests/linux/cap/shell_expand_guest_path.rb b/plugins/guests/linux/cap/shell_expand_guest_path.rb
index cc32d7f7c..9065873b2 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
diff --git a/plugins/guests/netbsd/cap/shell_expand_guest_path.rb b/plugins/guests/netbsd/cap/shell_expand_guest_path.rb
index 8471f4724..4dce5e2d6 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
diff --git a/plugins/guests/openbsd/cap/shell_expand_guest_path.rb b/plugins/guests/openbsd/cap/shell_expand_guest_path.rb
index 653493548..b1a82813f 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
diff --git a/plugins/provisioners/file/provisioner.rb b/plugins/provisioners/file/provisioner.rb
index 3c8081fce..46355c11b 100644
--- a/plugins/provisioners/file/provisioner.rb
+++ b/plugins/provisioners/file/provisioner.rb
@@ -18,10 +18,10 @@ module VagrantPlugins
             #
             # 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
+            command = "mkdir -p \"%s\"" % destination
             source << "/."
           else
-            command = "mkdir -p %s" % File.dirname(destination)
+            command = "mkdir -p \"%s\"" % File.dirname(destination)
           end
           comm.execute(command)
 
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