diff --git a/plugins/guests/darwin/cap/darwin_version.rb b/plugins/guests/darwin/cap/darwin_version.rb
new file mode 100644
index 000000000..5168c6f55
--- /dev/null
+++ b/plugins/guests/darwin/cap/darwin_version.rb
@@ -0,0 +1,40 @@
+module VagrantPlugins
+  module GuestDarwin
+    module Cap
+      class DarwinVersion
+        
+        VERSION_REGEX = /\d+.\d+.?\d*/.freeze
+
+        # Get the darwin version
+        #
+        # @param [Machine]
+        # @return [String] version of drawin
+        def self.darwin_version(machine)
+          output = ""
+          machine.communicate.sudo("sysctl kern.osrelease") do |_, data|
+            output = data
+          end
+          output.scan(VERSION_REGEX).first
+        end
+
+        # Get the darwin major version
+        #
+        # @param [Machine]
+        # @return [int] major version of drawin (nil if version is not detected)
+        def self.darwin_major_version(machine)
+          output = ""
+          machine.communicate.sudo("sysctl kern.osrelease") do |_, data|
+            output = data
+          end
+          version_string = output.scan(VERSION_REGEX).first
+          if version_string
+            major_version = version_string.split(".").first.to_i
+          else
+            major_version = nil
+          end
+          major_version
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/guests/darwin/cap/mount_vmware_shared_folder.rb b/plugins/guests/darwin/cap/mount_vmware_shared_folder.rb
index 29f2dac79..d4c6e2413 100644
--- a/plugins/guests/darwin/cap/mount_vmware_shared_folder.rb
+++ b/plugins/guests/darwin/cap/mount_vmware_shared_folder.rb
@@ -4,6 +4,9 @@ module VagrantPlugins
   module GuestDarwin
     module Cap
       class MountVmwareSharedFolder
+
+        MACOS_BIGSUR_DARWIN_VERSION = 20.freeze
+
         # Entry point for hook to called delayed actions
         # which finalizing the synced folders setup on
         # the guest
@@ -81,9 +84,16 @@ module VagrantPlugins
                   content = @apply_firmlinks[machine.id][:content].join("\n")
                   # Write out the synthetic file
                   comm.sudo("echo -e #{content.inspect} > /etc/synthetic.conf")
-                  if @apply_firmlinks[:bootstrap]
+                  if @apply_firmlinks[machine.id][:bootstrap]
+                    if machine.guest.capability("darwin_major_version").to_i < MACOS_BIGSUR_DARWIN_VERSION
+                      apfs_bootstrap_flag = "-B"
+                      expected_rc = 0
+                    else
+                      apfs_bootstrap_flag = "-t"
+                      expected_rc = 253
+                    end
                     # Re-bootstrap the root container to pick up firmlink updates
-                    comm.sudo("/System/Library/Filesystems/apfs.fs/Contents/Resources/apfs.util -B")
+                    comm.sudo("/System/Library/Filesystems/apfs.fs/Contents/Resources/apfs.util #{apfs_bootstrap_flag}", good_exit: [expected_rc])
                   end
                 end
               end
diff --git a/plugins/guests/darwin/plugin.rb b/plugins/guests/darwin/plugin.rb
index afda31843..d61a2d890 100644
--- a/plugins/guests/darwin/plugin.rb
+++ b/plugins/guests/darwin/plugin.rb
@@ -31,6 +31,16 @@ module VagrantPlugins
         Cap::ConfigureNetworks
       end
 
+      guest_capability(:darwin, :darwin_version) do
+        require_relative "cap/darwin_version"
+        Cap::DarwinVersion
+      end
+
+      guest_capability(:darwin, :darwin_major_version) do
+        require_relative "cap/darwin_version"
+        Cap::DarwinVersion
+      end
+
       guest_capability(:darwin, :halt) do
         require_relative "cap/halt"
         Cap::Halt
diff --git a/test/unit/plugins/guests/darwin/cap/darwin_version_test.rb b/test/unit/plugins/guests/darwin/cap/darwin_version_test.rb
new file mode 100644
index 000000000..5f1d9790a
--- /dev/null
+++ b/test/unit/plugins/guests/darwin/cap/darwin_version_test.rb
@@ -0,0 +1,49 @@
+require_relative "../../../../base"
+
+describe "VagrantPlugins::GuestDarwin::Cap::DarwinVersion" 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
+
+  after do
+    comm.verify_expectations!
+  end
+
+  describe ".darwin_version" do
+    let(:cap) { caps.get(:darwin_version) }
+
+    {
+      "kern.osrelease: 19.6.0" => "19.6.0",
+      "kern.osrelease: 20.1.10" => "20.1.10",
+    }.each do |str, expected|
+      it "returns #{expected} for #{str}" do
+        comm.stub_command("sysctl kern.osrelease", stdout: str)
+        expect(cap.darwin_version(machine)).to eq(expected)
+      end
+    end
+  end
+
+  describe ".darwin_major_version" do
+    let(:cap) { caps.get(:darwin_major_version) }
+
+    {
+      "kern.osrelease: 19.6.0" => 19,
+      "kern.osrelease: 20.1.10" => 20,
+      "" => nil
+    }.each do |str, expected|
+      it "returns #{expected} for #{str}" do
+        comm.stub_command("sysctl kern.osrelease", stdout: str)
+        expect(cap.darwin_major_version(machine)).to eq(expected)
+      end
+    end
+  end
+end
diff --git a/test/unit/plugins/guests/darwin/cap/mount_vmware_shared_folder_test.rb b/test/unit/plugins/guests/darwin/cap/mount_vmware_shared_folder_test.rb
index a706caa21..44302cb53 100644
--- a/test/unit/plugins/guests/darwin/cap/mount_vmware_shared_folder_test.rb
+++ b/test/unit/plugins/guests/darwin/cap/mount_vmware_shared_folder_test.rb
@@ -8,7 +8,8 @@ describe "VagrantPlugins::GuestDarwin::Cap::MountVmwareSharedFolder" do
       .get(:mount_vmware_shared_folder)
   end
 
-  let(:machine) { double("machine", communicate: communicator, id: "MACHINE_ID") }
+  let(:machine) { double("machine", communicate: communicator, id: "MACHINE_ID", guest: guest) }
+  let(:guest) {double("guest")}
   let(:communicator) { double("communicator") }
 
   before do
@@ -27,8 +28,9 @@ describe "VagrantPlugins::GuestDarwin::Cap::MountVmwareSharedFolder" do
       described_class.reset!
     end
 
-    after { described_class.
-        mount_vmware_shared_folder(machine, name, guestpath, options) }
+    after { 
+      described_class.mount_vmware_shared_folder(machine, name, guestpath, options) 
+    }
 
     context "with APFS root container" do
       before do
@@ -73,6 +75,21 @@ describe "VagrantPlugins::GuestDarwin::Cap::MountVmwareSharedFolder" do
           expect(communicator).to receive(:sudo).with(%r{ln -s .+/System/Volumes/Data.+})
         end
 
+        {
+          19 => "-B",
+          20 => "-t",
+          21 => "-t",
+          nil => "-B"
+        }.each do |version, expected_flag|
+          it "should re-bootstrap root dir for darwin version #{version}" do
+            expect(communicator).to receive(:sudo).with(/apfs.util #{expected_flag}/, any_args)
+            expect(guest).to receive(:capability).with("darwin_major_version").and_return(version)
+
+            described_class.mount_vmware_shared_folder(machine, name, guestpath, options) 
+            described_class.apfs_firmlinks_delayed[machine.id].call
+          end
+        end
+
         context "when firmlink is provided by the system" do
           before { expect(described_class).to receive(:system_firmlink?).and_return(true) }