diff --git a/lib/vagrant/util/downloader.rb b/lib/vagrant/util/downloader.rb
index 936cc000d01..9979bdb7e9a 100644
--- a/lib/vagrant/util/downloader.rb
+++ b/lib/vagrant/util/downloader.rb
@@ -104,6 +104,7 @@ def download!
         @logger.info("  -- Destination: #{@destination}")
 
         retried = false
+        retried_auth = false
         begin
           # Get the command line args and the subprocess opts based
           # on our downloader settings.
@@ -118,10 +119,24 @@ def download!
           execute_curl(options, subprocess_options, &data_proc)
         rescue Errors::DownloaderError => e
           # If we already retried, raise it.
-          raise if retried
+          if retried && retried_auth
+            raise
+          end
 
           @logger.error("Exit code: #{e.extra_data[:code]}")
 
+          # If a 401 is returned and we included an Authorization header,
+          # retry once without the Authorization header. This allows access
+          # to public resources when a stale/expired token is present.
+          if !retried_auth && Array(@headers).any? { |h| h =~ /^Authorization\b/i } &&
+             e.extra_data[:message].to_s.include?("401")
+            @logger.warn("Download received 401 with Authorization header present. Retrying without Authorization header.")
+            # Remove Authorization header for retry
+            @headers = Array(@headers).reject { |h| h =~ /^Authorization\b/i }
+            retried_auth = true
+            retry
+          end
+
           # If its any error other than 33, it is an error.
           raise if e.extra_data[:code].to_i != 33
 
@@ -156,8 +171,30 @@ def head
         options << @source
 
         @logger.info("HEAD: #{@source}")
-        result = execute_curl(options, subprocess_options)
-        result.stdout
+        begin
+          result = execute_curl(options, subprocess_options)
+          return result.stdout
+        rescue Errors::DownloaderError => e
+          # If a 401 is returned and we included an Authorization header,
+          # retry once without the Authorization header. This allows access
+          # to public resources when a stale/expired token is present.
+          if Array(@headers).any? { |h| h =~ /^Authorization\b/i } &&
+             e.extra_data[:message].to_s.include?("401")
+            @logger.warn("HEAD request received 401 with Authorization header present. Retrying without Authorization header.")
+            begin
+              # Remove Authorization header and retry
+              @headers = Array(@headers).reject { |h| h =~ /^Authorization\b/i }
+              options, subprocess_options = self.options
+              options.unshift("-I")
+              options << @source
+              result = execute_curl(options, subprocess_options)
+              return result.stdout
+            ensure
+              # Keep Authorization removed after a 401 to avoid repeated failures
+            end
+          end
+          raise
+        end
       end
 
       protected
diff --git a/test/unit/vagrant/util/downloader_test.rb b/test/unit/vagrant/util/downloader_test.rb
index bcbe02a086d..c5b00698560 100644
--- a/test/unit/vagrant/util/downloader_test.rb
+++ b/test/unit/vagrant/util/downloader_test.rb
@@ -63,6 +63,36 @@
       end
     end
 
+    context "when server returns 401 with Authorization header" do
+      let(:source) { "http://example.org/vagrant.box" }
+      let(:options) { {headers: ["Authorization: Bearer expired"]} }
+
+      let(:subprocess_401) do
+        double("subprocess_401").tap do |result|
+          allow(result).to receive(:exit_code).and_return(22)
+          allow(result).to receive(:stderr).and_return("curl: (22) The requested URL returned error: 401")
+        end
+      end
+
+      it "retries without the Authorization header and succeeds" do
+        first_call = ["-q", "--fail", "--location", "--max-redirs", "10",
+                      "--verbose", "--user-agent", described_class::USER_AGENT,
+                      "-H", "Authorization: Bearer expired",
+                      "--output", destination, source, {}]
+        second_call = ["-q", "--fail", "--location", "--max-redirs", "10",
+                       "--verbose", "--user-agent", described_class::USER_AGENT,
+                       "--output", destination, source, {}]
+
+        expect(Vagrant::Util::Subprocess).to receive(:execute).
+          with("curl", *first_call).ordered.and_return(subprocess_401)
+
+        expect(Vagrant::Util::Subprocess).to receive(:execute).
+          with("curl", *second_call).ordered.and_return(subprocess_result)
+
+        expect(subject.download!).to be(true)
+      end
+    end
+
     context "with UI" do
       let(:ui) { Vagrant::UI::Silent.new }
       let(:options) { {ui: ui} }
@@ -320,6 +350,47 @@
 
       expect(subject.head).to eq("foo")
     end
+
+    context "when server returns 401 with Authorization header" do
+      let(:source) { "http://example.org/metadata.json" }
+      let(:options) { {headers: ["Authorization: Bearer expired"]} }
+
+      let(:subprocess_401) do
+        double("subprocess_401").tap do |result|
+          allow(result).to receive(:exit_code).and_return(22)
+          allow(result).to receive(:stderr).and_return("curl: (22) The requested URL returned error: 401")
+          allow(result).to receive(:stdout).and_return("")
+        end
+      end
+
+      let(:subprocess_ok) do
+        double("subprocess_ok").tap do |result|
+          allow(result).to receive(:exit_code).and_return(0)
+          allow(result).to receive(:stderr).and_return("")
+          allow(result).to receive(:stdout).and_return("HTTP/1.1 200 OK\nContent-Type: application/json")
+        end
+      end
+
+      it "retries without the Authorization header and succeeds" do
+        # First attempt should include Authorization header and fail with 401
+        first_call = ["-q", "-I", "--fail", "--location", "--max-redirs", "10",
+                      "--verbose", "--user-agent", described_class::USER_AGENT,
+                      "-H", "Authorization: Bearer expired",
+                      source, {}]
+        expect(Vagrant::Util::Subprocess).to receive(:execute).
+          with("curl", *first_call).ordered.and_return(subprocess_401)
+
+        # Second attempt should exclude Authorization header and succeed
+        second_call = ["-q", "-I", "--fail", "--location", "--max-redirs", "10",
+                       "--verbose", "--user-agent", described_class::USER_AGENT,
+                       source, {}]
+        expect(Vagrant::Util::Subprocess).to receive(:execute).
+          with("curl", *second_call).ordered.and_return(subprocess_ok)
+
+        # Should not raise and should return the successful output
+        expect(subject.head).to include("Content-Type: application/json")
+      end
+    end
   end
 
   describe "#options" do