diff --git a/plugins/guests/linux/cap/reboot.rb b/plugins/guests/linux/cap/reboot.rb
index 0ac7d302d..9c1cb3132 100644
--- a/plugins/guests/linux/cap/reboot.rb
+++ b/plugins/guests/linux/cap/reboot.rb
@@ -6,7 +6,7 @@ module VagrantPlugins
     module Cap
       class Reboot
         extend Vagrant::Util::GuestInspection::Linux
-        MAX_REBOOT_RETRY_DURATION = 120
+        MAX_REBOOT_RETRY_DURATION = ENV.fetch('VAGRANT_MAX_REBOOT_RETRY_TIMEOUT', 120).to_i
 
         def self.reboot(machine)
           @logger = Log4r::Logger.new("vagrant::linux::reboot")
diff --git a/plugins/guests/windows/cap/reboot.rb b/plugins/guests/windows/cap/reboot.rb
index 70f10a41a..b0e92c02d 100644
--- a/plugins/guests/windows/cap/reboot.rb
+++ b/plugins/guests/windows/cap/reboot.rb
@@ -4,7 +4,7 @@ module VagrantPlugins
   module GuestWindows
     module Cap
       class Reboot
-        MAX_REBOOT_RETRY_DURATION = 120
+        MAX_REBOOT_RETRY_DURATION = ENV.fetch('VAGRANT_MAX_REBOOT_RETRY_TIMEOUT', 120).to_i
 
         def self.reboot(machine)
           @logger = Log4r::Logger.new("vagrant::windows::reboot")
diff --git a/test/unit/plugins/guests/linux/cap/reboot_test.rb b/test/unit/plugins/guests/linux/cap/reboot_test.rb
index bffc8daf1..d5ae18388 100644
--- a/test/unit/plugins/guests/linux/cap/reboot_test.rb
+++ b/test/unit/plugins/guests/linux/cap/reboot_test.rb
@@ -75,5 +75,22 @@ describe "VagrantPlugins::GuestLinux::Cap::Reboot" do
         end
       end
     end
+
+    context "reboot configuration" do
+      before do
+        allow(communicator).to receive(:execute)
+        expect(communicator).to receive(:execute).with(/reboot/, nil).and_return(0)
+        allow(described_class).to receive(:sleep)
+        allow(described_class).to receive(:wait_for_reboot).and_raise(Vagrant::Errors::MachineGuestNotReady)
+      end
+
+      describe ".reboot default" do
+        it "allows setting a custom max reboot retry duration" do
+          max_retries = 26 # initial call + 25 retries since multiple of 5
+          expect(described_class).to receive(:wait_for_reboot).exactly(max_retries).times
+          expect { described_class.reboot(machine) }.to raise_error(Vagrant::Errors::MachineGuestNotReady)
+        end
+      end
+    end
   end
 end
diff --git a/test/unit/plugins/guests/windows/cap/reboot_test.rb b/test/unit/plugins/guests/windows/cap/reboot_test.rb
index b7562cce2..114098758 100644
--- a/test/unit/plugins/guests/windows/cap/reboot_test.rb
+++ b/test/unit/plugins/guests/windows/cap/reboot_test.rb
@@ -112,4 +112,22 @@ describe "VagrantPlugins::GuestWindows::Cap::Reboot" do
       end
     end
   end
+
+  context "reboot configuration" do
+    before do
+      allow(communicator).to receive(:execute)
+      expect(communicator).to receive(:test).with(/# Function/, { error_check: false, shell: :powershell }).and_return(0)
+      expect(communicator).to receive(:execute).with(/shutdown/, { shell: :powershell }).and_return(0)
+      allow(described_class).to receive(:sleep)
+      allow(described_class).to receive(:wait_for_reboot).and_raise(StandardError)
+    end
+
+    describe ".reboot default" do
+      it "allows setting a custom max reboot retry duration" do
+        max_retries = 26 # initial call + 25 retries since multiple of 5
+        expect(described_class).to receive(:wait_for_reboot).exactly(max_retries).times
+        expect { described_class.reboot(machine) }.to raise_error(Exception)
+      end
+    end
+  end
 end