diff --git a/lib/vagrant/util.rb b/lib/vagrant/util.rb
index f8be2baf0..b7f297169 100644
--- a/lib/vagrant/util.rb
+++ b/lib/vagrant/util.rb
@@ -11,6 +11,7 @@ module Vagrant
     autoload :HashWithIndifferentAccess, 'vagrant/util/hash_with_indifferent_access'
     autoload :GuestInspection,           'vagrant/util/guest_inspection'
     autoload :LoggingFormatter,          'vagrant/util/logging_formatter'
+    autoload :Numeric,                   'vagrant/util/numeric'
     autoload :Platform,                  'vagrant/util/platform'
     autoload :Retryable,                 'vagrant/util/retryable'
     autoload :SafeExec,                  'vagrant/util/safe_exec'
diff --git a/lib/vagrant/util/numeric.rb b/lib/vagrant/util/numeric.rb
index 93346b81d..93c73e113 100644
--- a/lib/vagrant/util/numeric.rb
+++ b/lib/vagrant/util/numeric.rb
@@ -49,6 +49,26 @@ module Vagrant
           bytes
         end
 
+        # Convert bytes to a user friendly string representation
+        #
+        # @param [Numeric] bytes Number of bytes to represent
+        # @return [String] user friendly output
+        def bytes_to_string(bytes)
+          # We want to locate the size that will return the
+          # smallest whole value number
+          BYTES_CONVERSION_MAP.sort { |a, b|
+            b.last <=> a.last
+          }.each do |suffix, size|
+            val = bytes.to_f / size
+            next if val < 1
+            val = sprintf("%.2f", val)
+            val.slice!(-1, 1) while val.end_with?("0")
+            val.slice!(-1, 1) if val.end_with?(".")
+            return "#{val}#{suffix}"
+          end
+          "#{bytes} byte#{"s" if bytes > 1}"
+        end
+
         # Rounds actual value to two decimal places
         #
         # @param [Integer] bytes
diff --git a/plugins/commands/cloud/locales/en.yml b/plugins/commands/cloud/locales/en.yml
index 713282261..c819aaaa5 100644
--- a/plugins/commands/cloud/locales/en.yml
+++ b/plugins/commands/cloud/locales/en.yml
@@ -75,6 +75,10 @@ en:
         Updated provider %{provider} on %{org}/%{box_name} for version %{version}
       not_found: |-
         Failed to locate %{provider_name} provider for %{org}/%{box_name} on version %{version}
+      direct_disable: |-
+        Vagrant is automatically disabling direct upload to backend storage.
+        Uploads directly to backend storage are currently only supported for
+        files 5G in size or smaller. Box file to upload is: %{size}
     version:
       create_success: |-
         Created version %{version} on %{org}/%{box_name} for version %{version}
diff --git a/plugins/commands/cloud/provider/upload.rb b/plugins/commands/cloud/provider/upload.rb
index 41b8e0613..6cf053b64 100644
--- a/plugins/commands/cloud/provider/upload.rb
+++ b/plugins/commands/cloud/provider/upload.rb
@@ -58,6 +58,16 @@ module VagrantPlugins
               access_token: access_token
             )
 
+            # Include size check on file and disable direct if over 5G
+            if options[:direct]
+              fsize = File.stat(file).size
+              if fsize > (5 * Vagrant::Util::Numeric::GIGABYTE)
+                box_size = Vagrant::Util::Numeric.bytes_to_string(fsize)
+                @env.ui.warn(I18n.t("cloud_command.provider.direct_disable", size: box_size))
+                options[:direct] = false
+              end
+            end
+
             with_provider(account: account, org: org, box: box, version: version, provider: provider) do |p|
               p.upload(direct: options[:direct]) do |upload_url|
                 m = options[:direct] ? :put : :put
diff --git a/plugins/commands/cloud/publish.rb b/plugins/commands/cloud/publish.rb
index a136eafb8..93acbcef4 100644
--- a/plugins/commands/cloud/publish.rb
+++ b/plugins/commands/cloud/publish.rb
@@ -129,6 +129,16 @@ module VagrantPlugins
         def upload_box_file(provider, box_file, options={})
           box_file = File.absolute_path(box_file)
           @env.ui.info(I18n.t("cloud_command.publish.upload_provider", file: box_file))
+          # Include size check on file and disable direct if over 5G
+          if options[:direct_upload]
+            fsize = File.stat(box_file).size
+            if fsize > (5 * Vagrant::Util::Numeric::GIGABYTE)
+              box_size = Vagrant::Util::Numeric.bytes_to_string(fsize)
+              @env.ui.warn(I18n.t("cloud_command.provider.direct_disable", size: box_size))
+              options[:direct_upload] = false
+            end
+          end
+
           provider.upload(direct: options[:direct_upload]) do |upload_url|
             Vagrant::Util::Uploader.new(upload_url, box_file, ui: @env.ui, method: :put).upload!
           end
diff --git a/test/unit/plugins/commands/cloud/provider/upload_test.rb b/test/unit/plugins/commands/cloud/provider/upload_test.rb
index 66d18c89f..a25868c4c 100644
--- a/test/unit/plugins/commands/cloud/provider/upload_test.rb
+++ b/test/unit/plugins/commands/cloud/provider/upload_test.rb
@@ -15,6 +15,7 @@ describe VagrantPlugins::CloudCommand::ProviderCommand::Command::Upload do
   let(:version) { double("version", version: box_version, provdiers: [provider]) }
   let(:provider) { double("provider", name: box_version_provider) }
   let(:provider_file) { double("provider-file") }
+  let(:provider_file_size) { 1 }
 
   describe "#upload_provider" do
     let(:argv) { [] }
@@ -42,6 +43,8 @@ describe VagrantPlugins::CloudCommand::ProviderCommand::Command::Upload do
       allow(uploader).to receive(:upload!)
       allow(Vagrant::UI::Prefixed).to receive(:new).with(ui, "cloud").and_return(ui)
       allow(Vagrant::Util::Uploader).to receive(:new).and_return(uploader)
+      allow(File).to receive(:stat).with(provider_file).
+        and_return(double("provider-stat", size: provider_file_size))
     end
 
     subject { described_class.new(argv, env) }
@@ -91,6 +94,28 @@ describe VagrantPlugins::CloudCommand::ProviderCommand::Command::Upload do
         end
         subject.upload_provider(org_name, box_name, box_version, box_version_provider, provider_file, access_token, options)
       end
+
+      context "when file size is 5GB" do
+        let(:provider_file_size) { 5368709120 }
+
+        it "should use direct upload" do
+          expect(provider).to receive(:upload) do |**args|
+            expect(args[:direct]).to be_truthy
+          end
+          subject.upload_provider(org_name, box_name, box_version, box_version_provider, provider_file, access_token, options)
+        end
+      end
+
+      context "when file size is greater than 5GB" do
+        let(:provider_file_size) { 5368709121 }
+
+        it "should disable direct upload" do
+          expect(provider).to receive(:upload) do |**args|
+            expect(args[:direct]).to be_falsey
+          end
+          subject.upload_provider(org_name, box_name, box_version, box_version_provider, provider_file, access_token, options)
+        end
+      end
     end
   end
 
diff --git a/test/unit/plugins/commands/cloud/publish_test.rb b/test/unit/plugins/commands/cloud/publish_test.rb
index 4c7b584ad..bc25feaf0 100644
--- a/test/unit/plugins/commands/cloud/publish_test.rb
+++ b/test/unit/plugins/commands/cloud/publish_test.rb
@@ -10,6 +10,7 @@ describe VagrantPlugins::CloudCommand::Command::Publish do
   let(:account) { double("account") }
   let(:organization) { double("organization") }
   let(:box) { double("box") }
+  let(:box_size) { 1 }
   let(:version) { double("version") }
   let(:provider) { double("provider") }
   let(:uploader) { double("uploader") }
@@ -25,6 +26,8 @@ describe VagrantPlugins::CloudCommand::Command::Publish do
     allow(ui).to receive(:success)
     allow(ui).to receive(:error)
     allow(iso_env).to receive(:ui).and_return(ui)
+    allow(File).to receive(:stat).with(box).
+      and_return(double("box_stat", size: box_size))
     allow(VagrantCloud::Account).to receive(:new).
       with(custom_server: anything, access_token: anything).
       and_return(account)
@@ -60,10 +63,30 @@ describe VagrantPlugins::CloudCommand::Command::Publish do
       subject.upload_box_file(provider, box)
     end
 
-    it "should upload with PUT method when direct upload option set" do
-      expect(Vagrant::Util::Uploader).to receive(:new).
-        with(upload_url, anything, hash_including(method: :put)).and_return(uploader)
-      subject.upload_box_file(provider, box, direct_upload: true)
+    context "with direct upload option enabled" do
+      it "should upload with PUT method when direct upload option set" do
+        expect(Vagrant::Util::Uploader).to receive(:new).
+          with(upload_url, anything, hash_including(method: :put)).and_return(uploader)
+        subject.upload_box_file(provider, box, direct_upload: true)
+      end
+
+      context "with box size of 5GB" do
+        let(:box_size) { 5368709120 }
+
+        it "should upload using direct to storage option" do
+          expect(provider).to receive(:upload).with(direct: true)
+          subject.upload_box_file(provider, box, direct_upload: true)
+        end
+      end
+
+      context "with box size greater than 5GB" do
+        let(:box_size) { 5368709121 }
+
+        it "should disable direct to storage upload" do
+          expect(provider).to receive(:upload).with(direct: false)
+          subject.upload_box_file(provider, box, direct_upload: true)
+        end
+      end
     end
   end
 
@@ -220,6 +243,8 @@ describe VagrantPlugins::CloudCommand::Command::Publish do
     let(:client) { double("client", token: "1234token1234") }
     let(:action_runner) { double("action_runner") }
     let(:box_path) { "path/to/the/virtualbox.box" }
+    let(:full_box_path) { "/full/#{box_path}" }
+    let(:box) { full_box_path }
 
     before do
       allow(iso_env).to receive(:action_runner).
@@ -229,8 +254,10 @@ describe VagrantPlugins::CloudCommand::Command::Publish do
       allow(subject).to receive(:format_box_results)
 
       allow(iso_env.ui).to receive(:ask).and_return("y")
-      allow(File).to receive(:absolute_path).and_return("/full/#{box_path}")
-      allow(File).to receive(:file?).and_return(true)
+      allow(File).to receive(:absolute_path).with(box_path)
+        .and_return("/full/#{box_path}")
+      allow(File).to receive(:file?).with(box_path)
+        .and_return(true)
     end
 
     context "with no arguments" do