diff --git a/internal/cli/dynamic.go b/internal/cli/dynamic.go
index b472d90fd..e2f85831e 100644
--- a/internal/cli/dynamic.go
+++ b/internal/cli/dynamic.go
@@ -101,14 +101,25 @@ func (c *DynamicCommand) Run(args []string) int {
 		} else if !r.RunResult {
 			runErrorStatus := status.FromProto(r.RunError)
 			details := runErrorStatus.Details()
+			userError := false
 			for _, msg := range details {
 				switch m := msg.(type) {
 				case *errdetails.LocalizedMessage:
-					cl.UI().Output("Error: "+m.Message+"\n", terminal.WithErrorStyle())
+					// Errors from Ruby with LocalizedMessages are user-facing,
+					// so can be output directly.
+					userError = true
+					cl.UI().Output(m.Message, terminal.WithErrorStyle())
+					// All user-facing errors from Ruby use a 1 exit code. See
+					// Vagrant::Errors::VagrantError.
+					r.ExitCode = 1
+
 				}
 			}
-			runErr := status.FromProto(r.RunError)
-			err = fmt.Errorf("execution failed, %w", runErr.Err())
+			if !userError {
+				runErr := status.FromProto(r.RunError)
+				err = runErr.Err()
+				cl.UI().Output("Unexpected Error: "+err.Error()+"\n", terminal.WithErrorStyle())
+			}
 		}
 
 		c.Log.Debug("result from operation", "task", c.name, "result", r)
@@ -117,9 +128,11 @@ func (c *DynamicCommand) Run(args []string) int {
 	})
 
 	if err != nil {
+		c.Log.Error("Got error from task, so exiting 255", "error", err)
 		return int(-1)
 	}
 
+	c.Log.Info("Task did not error, so exiting with provided code", "code", r.ExitCode)
 	return int(r.ExitCode)
 }
 
diff --git a/plugins/commands/serve/util/exception_transformer.rb b/plugins/commands/serve/util/exception_transformer.rb
index ee3ef6a05..d8c4779af 100644
--- a/plugins/commands/serve/util/exception_transformer.rb
+++ b/plugins/commands/serve/util/exception_transformer.rb
@@ -1,3 +1,4 @@
+require 'google/protobuf/well_known_types'
 require 'google/rpc/error_details_pb'
 
 module VagrantPlugins
@@ -5,8 +6,6 @@ module VagrantPlugins
     module Util
       # Adds exception logging to all public instance methods
       module ExceptionTransformer
-        prepend Util::HasMapper
-
         def self.included(klass)
           # Get all the public instance methods. Need to search ancestors as well
           # for modules like the Guest service which includes the CapabilityPlatform
@@ -52,25 +51,25 @@ module VagrantPlugins
                 # headers below the limit in most cases.
                 message = ExceptionTransformer.truncate_to(err.message, 1024)
                 backtrace = ExceptionTransformer.truncate_to(err.backtrace.join("\n"), 1024)
-                localized_msg_details_any = Google::Protobuf::Any.new
-                localized_msg_details_any.pack(
-                  # This is the message we expect to be unpacked and presented
-                  # to the user, as it's sometimes a user-facing error.
-                  Google::Rpc::LocalizedMessage.new(
-                    locale: "en-US", message: message
+                metadata = {}
+
+                # VagrantErrors are user-facing and so get their message packed
+                # into the details.
+                if err.is_a? Vagrant::Errors::VagrantError
+                  localized_msg_details_any = Google::Protobuf::Any.new
+                  localized_msg_details_any.pack(
+                    Google::Rpc::LocalizedMessage.new(locale: "en-US", message: message)
                   )
-                )
-                proto = Google::Rpc::Status.new(
-                  code: GRPC::Core::StatusCodes::UNKNOWN,
-                  message: "#{message}\n#{backtrace}",
-                  details: [localized_msg_details_any]
-                )
-                encoded_proto = Google::Rpc::Status.encode(proto)
-                grpc_status_details_bin_trailer = 'grpc-status-details-bin'
+                  proto = Google::Rpc::Status.new(
+                    code: GRPC::Core::StatusCodes::UNKNOWN,
+                    details: [localized_msg_details_any]
+                  )
+                  metadata[GRPC_DETAILS_METADATA_KEY] = Google::Rpc::Status.encode(proto)
+                end
                 grpc_error = GRPC::BadStatus.new(
                   GRPC::Core::StatusCodes::UNKNOWN,
-                  message,
-                  {grpc_status_details_bin_trailer => encoded_proto},
+                  "#{message}\n#{backtrace}",
+                  metadata,
                 )
                 raise grpc_error
               end
@@ -87,6 +86,8 @@ module VagrantPlugins
             str[0, len-3] + "..."
           end
         end
+
+        GRPC_DETAILS_METADATA_KEY = "grpc-status-details-bin".freeze
       end
     end
   end
diff --git a/test/unit/plugins/commands/serve/util/exception_transformer_test.rb b/test/unit/plugins/commands/serve/util/exception_transformer_test.rb
new file mode 100644
index 000000000..da2121d7f
--- /dev/null
+++ b/test/unit/plugins/commands/serve/util/exception_transformer_test.rb
@@ -0,0 +1,38 @@
+require File.expand_path("../../../../../base", __FILE__)
+
+require Vagrant.source_root.join("plugins/commands/serve/command")
+
+describe VagrantPlugins::CommandServe::Util::ExceptionTransformer do
+  include_context "unit"
+
+  it "converts VagrantErrors into GRPC::BadStatus errors with a LocalizedMessage" do
+    klass = Class.new
+    vagrant_error = Class.new(Vagrant::Errors::VagrantError) do
+      error_key("test_key")
+    end
+    klass.define_method(:wrapme) do |*args|
+      raise vagrant_error.new
+    end
+    subklass = Class.new(klass)
+    subklass.include described_class
+    expect {
+      subklass.new.wrapme
+    }.to raise_error(an_instance_of(GRPC::BadStatus).and satisfy { |err|
+      err.metadata["grpc-status-details-bin"] =~ /LocalizedMessage/
+    })
+  end
+
+  it "converts non-VagrantErrors into GRPC::BadStatus errors without a LocalizedMessage" do
+    klass = Class.new
+    klass.define_method(:wrapme) do
+      raise "just a regular error"
+    end
+    subklass = Class.new(klass)
+    subklass.include described_class
+    expect {
+      subklass.new.wrapme
+    }.to raise_error(an_instance_of(GRPC::BadStatus).and satisfy { |err|
+      err.metadata["grpc-status-details-bin"].nil?
+    })
+  end
+end