diff --git a/plugins/guests/debian/cap/configure_networks.rb b/plugins/guests/debian/cap/configure_networks.rb
index dfec32ccb..bb1ff69f9 100644
--- a/plugins/guests/debian/cap/configure_networks.rb
+++ b/plugins/guests/debian/cap/configure_networks.rb
@@ -8,6 +8,7 @@ module VagrantPlugins
       class ConfigureNetworks
         include Vagrant::Util
         extend Vagrant::Util::GuestInspection::Linux
+        extend Vagrant::Util::Retryable
 
         NETPLAN_DEFAULT_VERSION = 2
         NETPLAN_DIRECTORY = "/etc/netplan".freeze
@@ -166,11 +167,16 @@ module VagrantPlugins
             rm -f /tmp/vagrant-network-interfaces.post
           EOH
 
+          comm.sudo(commands.join("\n"))
+          network_up_commands = []
+         
           # Bring back up each network interface, reconfigured.
           networks.each do |network|
-            commands << "/sbin/ifup '#{network[:device]}'"
+            network_up_commands << "/sbin/ifup '#{network[:device]}'"
+          end
+          retryable(on: Vagrant::Errors::VagrantError, sleep: 2, tries: 2) do
+            comm.sudo(network_up_commands.join("\n"))
           end
-          comm.sudo(commands.join("\n"))
         end
 
         # Simple helper to upload content to guest temporary file
diff --git a/test/unit/plugins/guests/debian/cap/configure_networks_test.rb b/test/unit/plugins/guests/debian/cap/configure_networks_test.rb
index 8081de6fc..1898e3940 100644
--- a/test/unit/plugins/guests/debian/cap/configure_networks_test.rb
+++ b/test/unit/plugins/guests/debian/cap/configure_networks_test.rb
@@ -79,8 +79,9 @@ describe "VagrantPlugins::GuestDebian::Cap::ConfigureNetworks" do
       expect(comm.received_commands[0]).to match("/sbin/ip addr flush dev 'eth1'")
       expect(comm.received_commands[0]).to match("/sbin/ifdown 'eth2' || true")
       expect(comm.received_commands[0]).to match("/sbin/ip addr flush dev 'eth2'")
-      expect(comm.received_commands[0]).to match("/sbin/ifup 'eth1'")
-      expect(comm.received_commands[0]).to match("/sbin/ifup 'eth2'")
+      expect(comm.received_commands[1]).to match("/sbin/ifup 'eth1'")
+      expect(comm.received_commands[1]).to match("/sbin/ifup 'eth2'")
+
     end
 
     context "with systemd" do
@@ -96,8 +97,8 @@ describe "VagrantPlugins::GuestDebian::Cap::ConfigureNetworks" do
         expect(comm.received_commands[0]).to match("/sbin/ip addr flush dev 'eth1'")
         expect(comm.received_commands[0]).to match("/sbin/ifdown 'eth2' || true")
         expect(comm.received_commands[0]).to match("/sbin/ip addr flush dev 'eth2'")
-        expect(comm.received_commands[0]).to match("/sbin/ifup 'eth1'")
-        expect(comm.received_commands[0]).to match("/sbin/ifup 'eth2'")
+        expect(comm.received_commands[1]).to match("/sbin/ifup 'eth1'")
+        expect(comm.received_commands[1]).to match("/sbin/ifup 'eth2'")
       end
 
       context "with systemd-networkd" do