diff --git a/command/agent/agent.go b/command/agent/agent.go
index 13c896c7f..a31d008c2 100644
--- a/command/agent/agent.go
+++ b/command/agent/agent.go
@@ -170,7 +170,6 @@ func convertServerConfig(agentConfig *Config) (*nomad.Config, error) {
 	conf.EnableDebug = agentConfig.EnableDebug
 
 	conf.Build = agentConfig.Version.VersionNumber()
-	conf.BuildDate = agentConfig.Version.BuildDate
 	conf.Revision = agentConfig.Version.Revision
 	if agentConfig.Region != "" {
 		conf.Region = agentConfig.Region
@@ -550,9 +549,12 @@ func convertServerConfig(agentConfig *Config) (*nomad.Config, error) {
 	}
 
 	// Add Enterprise license configs
-	conf.LicenseEnv = agentConfig.Server.LicenseEnv
-	conf.LicensePath = agentConfig.Server.LicensePath
-	conf.LicenseConfig.AdditionalPubKeys = agentConfig.Server.licenseAdditionalPublicKeys
+	conf.LicenseConfig = &nomad.LicenseConfig{
+		BuildDate:         agentConfig.Version.BuildDate,
+		AdditionalPubKeys: agentConfig.Server.licenseAdditionalPublicKeys,
+		LicenseEnvBytes:   agentConfig.Server.LicenseEnv,
+		LicensePath:       agentConfig.Server.LicensePath,
+	}
 
 	// Add the search configuration
 	if search := agentConfig.Server.Search; search != nil {
diff --git a/nomad/config.go b/nomad/config.go
index 6c789aef4..191dd72af 100644
--- a/nomad/config.go
+++ b/nomad/config.go
@@ -127,9 +127,6 @@ type Config struct {
 	// operators track which versions are actively deployed
 	Build string
 
-	// BuildDate is the time of the git commit used to build the program.
-	BuildDate time.Time
-
 	// Revision is a string that carries the version.GitCommit of Nomad that
 	// was compiled.
 	Revision string
@@ -389,10 +386,8 @@ type Config struct {
 	// connections from a single IP address. nil/0 means no limit.
 	RPCMaxConnsPerClient int
 
-	// LicenseConfig is a tunable knob for enterprise license testing.
+	// LicenseConfig stores information about the Enterprise license loaded for the server.
 	LicenseConfig *LicenseConfig
-	LicenseEnv    string
-	LicensePath   string
 
 	// SearchConfig provides knobs for Search API.
 	SearchConfig *structs.SearchConfig
diff --git a/nomad/server_setup.go b/nomad/license_config.go
similarity index 91%
rename from nomad/server_setup.go
rename to nomad/license_config.go
index a37d8b517..59f0e1330 100644
--- a/nomad/server_setup.go
+++ b/nomad/license_config.go
@@ -3,7 +3,6 @@ package nomad
 import (
 	"time"
 
-	"github.com/hashicorp/go-hclog"
 	"golang.org/x/exp/slices"
 )
 
@@ -21,8 +20,6 @@ type LicenseConfig struct {
 
 	// AdditionalPubKeys is a set of public keys to
 	AdditionalPubKeys []string
-
-	Logger hclog.InterceptLogger
 }
 
 func (c *LicenseConfig) Copy() *LicenseConfig {
diff --git a/nomad/license_config_oss.go b/nomad/license_config_oss.go
new file mode 100644
index 000000000..32d00d39a
--- /dev/null
+++ b/nomad/license_config_oss.go
@@ -0,0 +1,7 @@
+//go:build !ent
+
+package nomad
+
+func (c *LicenseConfig) Validate() error {
+	return nil
+}
diff --git a/nomad/server.go b/nomad/server.go
index 7a2e268ae..4d4cb910d 100644
--- a/nomad/server.go
+++ b/nomad/server.go
@@ -345,6 +345,11 @@ func NewServer(config *Config, consulCatalog consul.CatalogAPI, consulConfigEntr
 	// Create the logger
 	logger := config.Logger.ResetNamedIntercept("nomad")
 
+	// Validate enterprise license before anything stateful happens
+	if err = config.LicenseConfig.Validate(); err != nil {
+		return nil, err
+	}
+
 	// Create the server
 	s := &Server{
 		config:                  config,
@@ -868,8 +873,11 @@ func (s *Server) Reload(newConfig *Config) error {
 		}
 	}
 
-	if newConfig.LicenseEnv != "" || newConfig.LicensePath != "" {
-		s.EnterpriseState.ReloadLicense(newConfig)
+	if newConfig.LicenseConfig.LicenseEnvBytes != "" || newConfig.LicenseConfig.LicensePath != "" {
+		if err = s.EnterpriseState.ReloadLicense(newConfig); err != nil {
+			s.logger.Error("error reloading license", "error", err)
+			_ = multierror.Append(&mErr, err)
+		}
 	}
 
 	// Because this is a new configuration, we extract the worker pool arguments without acquiring a lock
diff --git a/nomad/server_setup_oss.go b/nomad/server_setup_oss.go
index 5e0684729..b37657269 100644
--- a/nomad/server_setup_oss.go
+++ b/nomad/server_setup_oss.go
@@ -1,5 +1,4 @@
 //go:build !ent
-// +build !ent
 
 package nomad
 
diff --git a/nomad/testing.go b/nomad/testing.go
index d2ec5d616..de933f271 100644
--- a/nomad/testing.go
+++ b/nomad/testing.go
@@ -1,7 +1,6 @@
 package nomad
 
 import (
-	"errors"
 	"fmt"
 	"math/rand"
 	"net"
@@ -43,7 +42,11 @@ func TestServer(t testing.T, cb func(*Config)) (*Server, func()) {
 	return s, c
 }
 
-func TestServerErr(t testing.T, cb func(*Config)) (*Server, func(), error) {
+// TestConfigForServer provides a fully functional Config to pass to NewServer()
+// It can be changed beforehand to induce different behavior such as specific errors.
+func TestConfigForServer(t testing.T) *Config {
+	t.Helper()
+
 	// Setup the default settings
 	config := DefaultConfig()
 
@@ -95,6 +98,19 @@ func TestServerErr(t testing.T, cb func(*Config)) (*Server, func(), error) {
 		MinTermLength: 2,
 	}
 
+	// Get random ports for RPC and Serf
+	ports := ci.PortAllocator.Grab(2)
+	config.RPCAddr = &net.TCPAddr{
+		IP:   []byte{127, 0, 0, 1},
+		Port: ports[0],
+	}
+	config.SerfConfig.MemberlistConfig.BindPort = ports[1]
+
+	return config
+}
+
+func TestServerErr(t testing.T, cb func(*Config)) (*Server, func(), error) {
+	config := TestConfigForServer(t)
 	// Invoke the callback if any
 	if cb != nil {
 		cb(config)
@@ -104,18 +120,12 @@ func TestServerErr(t testing.T, cb func(*Config)) (*Server, func(), error) {
 	cConfigs := consul.NewMockConfigsAPI(config.Logger)
 	cACLs := consul.NewMockACLsAPI(config.Logger)
 
+	var server *Server
+	var err error
+
 	for i := 10; i >= 0; i-- {
-		// Get random ports, need to cleanup later
-		ports := ci.PortAllocator.Grab(2)
-
-		config.RPCAddr = &net.TCPAddr{
-			IP:   []byte{127, 0, 0, 1},
-			Port: ports[0],
-		}
-		config.SerfConfig.MemberlistConfig.BindPort = ports[1]
-
 		// Create server
-		server, err := NewServer(config, cCatalog, cConfigs, cACLs)
+		server, err = NewServer(config, cCatalog, cConfigs, cACLs)
 		if err == nil {
 			return server, func() {
 				ch := make(chan error)
@@ -145,9 +155,17 @@ func TestServerErr(t testing.T, cb func(*Config)) (*Server, func(), error) {
 			wait := time.Duration(rand.Int31n(2000)) * time.Millisecond
 			time.Sleep(wait)
 		}
+
+		// if it failed for port reasons, try new ones
+		ports := ci.PortAllocator.Grab(2)
+		config.RPCAddr = &net.TCPAddr{
+			IP:   []byte{127, 0, 0, 1},
+			Port: ports[0],
+		}
+		config.SerfConfig.MemberlistConfig.BindPort = ports[1]
 	}
 
-	return nil, nil, errors.New("unable to acquire ports for test server")
+	return nil, nil, fmt.Errorf("error starting test server: %w", err)
 }
 
 func TestJoin(t testing.T, servers ...*Server) {