diff --git a/changelog/fragments/1669929902-fix-local-fleet-server-port.yaml b/changelog/fragments/1669929902-fix-local-fleet-server-port.yaml
new file mode 100644
index 00000000000..08119ec5ac6
--- /dev/null
+++ b/changelog/fragments/1669929902-fix-local-fleet-server-port.yaml
@@ -0,0 +1,31 @@
+# Kind can be one of:
+# - breaking-change: a change to previously-documented behavior
+# - deprecation: functionality that is being removed in a later release
+# - bug-fix: fixes a problem in a previous version
+# - enhancement: extends functionality but does not break or fix existing behavior
+# - feature: new functionality
+# - known-issue: problems that we are aware of in a given version
+# - security: impacts on the security of a product or a user’s deployment.
+# - upgrade: important information for someone upgrading from a prior version
+# - other: does not fit into any of the other categories
+kind: bug-fix
+
+# Change summary; a 80ish characters long description of the change.
+summary: elastic-agent will use local port when running fleet-server
+
+# Long description; in case the summary is not enough to describe the change
+# this field accommodate a description without length limits.
+description: The elastic-agent will now use the 8221 locally bound port when running fleet-server instead of the external port (8220).
+
+# Affected component; a word indicating the component this changeset affects.
+component:
+
+# PR number; optional; the PR number that added the changeset.
+# If not present is automatically filled by the tooling finding the PR where this changelog fragment has been added.
+# NOTE: the tooling supports backports, so it's able to fill the original PR number instead of the backport PR number.
+# Please provide it if you are adding a fragment for a different PR.
+#pr: 1234
+
+# Issue number; optional; the GitHub issue related to this changeset (either closes or is part of).
+# If not present is automatically filled by the tooling with the issue linked to the PR number.
+#issue: 1234
diff --git a/internal/pkg/agent/cmd/enroll_cmd.go b/internal/pkg/agent/cmd/enroll_cmd.go
index 805b8a47757..14a49a3d217 100644
--- a/internal/pkg/agent/cmd/enroll_cmd.go
+++ b/internal/pkg/agent/cmd/enroll_cmd.go
@@ -230,6 +230,8 @@ func (c *enrollCmd) Execute(ctx context.Context, streams *cli.IOStreams) error {
 	if localFleetServer {
 		// Ensure that the agent does not use a proxy configuration
 		// when connecting to the local fleet server.
+		// Note that when running fleet-server the enroll request will be sent to :8220,
+		// however when the agent is running afterwards requests will be sent to :8221
 		c.remoteConfig.Transport.Proxy.Disable = true
 	}
 
@@ -301,6 +303,9 @@ func (c *enrollCmd) writeDelayEnroll(streams *cli.IOStreams) error {
 func (c *enrollCmd) fleetServerBootstrap(ctx context.Context, persistentConfig map[string]interface{}) (string, error) {
 	c.log.Debug("verifying communication with running Elastic Agent daemon")
 	agentRunning := true
+	if c.options.FleetServer.InternalPort == 0 {
+		c.options.FleetServer.InternalPort = defaultFleetServerInternalPort
+	}
 	_, err := getDaemonState(ctx)
 	if err != nil {
 		if !c.options.FleetServer.SpawnAgent {
@@ -336,6 +341,7 @@ func (c *enrollCmd) fleetServerBootstrap(ctx context.Context, persistentConfig m
 	if err != nil {
 		return "", err
 	}
+	c.options.FleetServer.InternalPort = fleetConfig.Server.InternalPort
 
 	configToStore := map[string]interface{}{
 		"agent": agentConfig,
@@ -545,6 +551,9 @@ func (c *enrollCmd) enroll(ctx context.Context, persistentConfig map[string]inte
 		// use internal URL for future requests
 		if c.options.InternalURL != "" {
 			fleetConfig.Client.Host = c.options.InternalURL
+			// fleet-server will bind the internal listenter to localhost:8221
+			// InternalURL is localhost:8221, however cert uses $HOSTNAME, so we need to disable hostname verification.
+			fleetConfig.Client.Transport.TLS.VerificationMode = tlscommon.VerifyCertificate
 		}
 	}
 
diff --git a/internal/pkg/remote/client.go b/internal/pkg/remote/client.go
index 5c8fd5c9a34..af77db8d0c2 100644
--- a/internal/pkg/remote/client.go
+++ b/internal/pkg/remote/client.go
@@ -174,6 +174,7 @@ func (c *Client) Send(
 				"fail to create HTTP request using method %s to %s: %w",
 				method, path, err)
 		}
+		c.log.Debugf("Creating new request to request URL %s", req.URL.String())
 
 		// Add generals headers to the request, we are dealing exclusively with JSON.
 		// Content-Type / Accepted type can be overridden by the caller.