diff --git a/cmd/api/src/api/auth.go b/cmd/api/src/api/auth.go
index 61f7621e33..c9be7787fb 100644
--- a/cmd/api/src/api/auth.go
+++ b/cmd/api/src/api/auth.go
@@ -1,17 +1,17 @@
 // Copyright 2023 Specter Ops, Inc.
-// 
+//
 // Licensed under the Apache License, Version 2.0
 // you may not use this file except in compliance with the License.
 // You may obtain a copy of the License at
-// 
+//
 //     http://www.apache.org/licenses/LICENSE-2.0
-// 
+//
 // Unless required by applicable law or agreed to in writing, software
 // distributed under the License is distributed on an "AS IS" BASIS,
 // WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
 // See the License for the specific language governing permissions and
 // limitations under the License.
-// 
+//
 // SPDX-License-Identifier: Apache-2.0
 
 package api
@@ -35,7 +35,9 @@ import (
 	"github.com/specterops/bloodhound/log"
 	"github.com/specterops/bloodhound/src/auth"
 	"github.com/specterops/bloodhound/src/config"
+	"github.com/specterops/bloodhound/src/ctx"
 	"github.com/specterops/bloodhound/src/database"
+	"github.com/specterops/bloodhound/src/database/types"
 	"github.com/specterops/bloodhound/src/model"
 )
 
@@ -84,22 +86,73 @@ func NewAuthenticator(cfg config.Configuration, db database.Database, ctxInitial
 	}
 }
 
-func (s authenticator) LoginWithSecret(ctx context.Context, loginRequest LoginRequest) (LoginDetails, error) {
+func (s authenticator) auditLogin(requestContext context.Context, commitID uuid.UUID, user model.User, loginRequest LoginRequest, status string, loginError error) {
+	bhCtx := ctx.Get(requestContext)
+	auditLog := model.AuditLog{
+		Action:          "LoginAttempt",
+		Fields:          types.JSONUntypedObject{"username": loginRequest.Username},
+		RequestID:       bhCtx.RequestID,
+		SourceIpAddress: bhCtx.RequestIP,
+		Status:          status,
+		CommitID:        commitID,
+	}
+
+	if user.PrincipalName != "" {
+		auditLog.ActorID = user.ID.String()
+		auditLog.ActorName = user.PrincipalName
+		auditLog.ActorEmail = user.EmailAddress.ValueOrZero()
+	}
+
+	if status == string(model.AuditStatusFailure) {
+		auditLog.Fields["error"] = loginError
+	}
+
+	s.db.CreateAuditLog(auditLog)
+}
+
+func (s authenticator) validateSecretLogin(ctx context.Context, loginRequest LoginRequest) (model.User, string, error) {
 	if user, err := s.db.LookupUser(loginRequest.Username); err != nil {
 		if errors.Is(err, database.ErrNotFound) {
-			return LoginDetails{}, ErrInvalidAuth
+			return model.User{}, "", ErrInvalidAuth
 		}
 
-		return LoginDetails{}, FormatDatabaseError(err)
+		return model.User{}, "", FormatDatabaseError(err)
 	} else if user.AuthSecret == nil {
-		return LoginDetails{}, ErrNoUserSecret
+		return user, "", ErrNoUserSecret
 	} else if err := s.ValidateSecret(ctx, loginRequest.Secret, *user.AuthSecret); err != nil {
-		return LoginDetails{}, err
-	} else if err := auth.ValidateTOTPSecret(loginRequest.OTP, *user.AuthSecret); err != nil {
-		return LoginDetails{}, err
+		return user, "", err
+	} else if err = auth.ValidateTOTPSecret(loginRequest.OTP, *user.AuthSecret); err != nil {
+		return user, "", err
 	} else if sessionToken, err := s.CreateSession(user, *user.AuthSecret); err != nil {
+		return user, "", err
+	} else {
+		return user, sessionToken, nil
+	}
+}
+
+func (s authenticator) LoginWithSecret(ctx context.Context, loginRequest LoginRequest) (LoginDetails, error) {
+	var (
+		commitID     uuid.UUID
+		err          error
+		sessionToken string
+		user         model.User
+	)
+
+	commitID, err = uuid.NewV4()
+	if err != nil {
+		log.Errorf("error generating commit ID for login: %s", err)
+		return LoginDetails{}, err
+	}
+
+	s.auditLogin(ctx, commitID, user, loginRequest, string(model.AuditStatusIntent), err)
+
+	user, sessionToken, err = s.validateSecretLogin(ctx, loginRequest)
+
+	if err != nil {
+		s.auditLogin(ctx, commitID, user, loginRequest, string(model.AuditStatusFailure), err)
 		return LoginDetails{}, err
 	} else {
+		s.auditLogin(ctx, commitID, user, loginRequest, string(model.AuditStatusSuccess), err)
 		return LoginDetails{
 			User:         user,
 			SessionToken: sessionToken,
diff --git a/cmd/api/src/api/middleware/middleware.go b/cmd/api/src/api/middleware/middleware.go
index 353f6fbc9a..8c2347cd11 100644
--- a/cmd/api/src/api/middleware/middleware.go
+++ b/cmd/api/src/api/middleware/middleware.go
@@ -19,6 +19,7 @@ package middleware
 import (
 	"context"
 	"fmt"
+	"net"
 	"net/http"
 	"net/url"
 	"strconv"
@@ -149,11 +150,21 @@ func ContextMiddleware(next http.Handler) http.Handler {
 }
 
 func parseUserIP(r *http.Request) string {
+	var remoteIp string
+
+	// The point of this code is to strip the port, so we don't need to save it.
+	if host, _, err := net.SplitHostPort(r.RemoteAddr); err != nil {
+		log.Warnf("Error parsing remoteAddress 's': %s", r.RemoteAddr, err)
+		remoteIp = r.RemoteAddr
+	} else {
+		remoteIp = host
+	}
+
 	if result := r.Header.Get("X-Forwarded-For"); result == "" {
 		log.Warnf("No data found in X-Forwarded-For header")
-		return r.RemoteAddr
+		return remoteIp
 	} else {
-		result += "," + r.RemoteAddr
+		result += "," + remoteIp
 		return result
 	}
 }
diff --git a/cmd/api/src/api/middleware/middleware_internal_test.go b/cmd/api/src/api/middleware/middleware_internal_test.go
index e1c26fa135..528204bd34 100644
--- a/cmd/api/src/api/middleware/middleware_internal_test.go
+++ b/cmd/api/src/api/middleware/middleware_internal_test.go
@@ -91,14 +91,14 @@ func TestParseUserIP_XForwardedFor_RemoteAddr(t *testing.T) {
 	req.Header.Set("X-Forwarded-For", strings.Join([]string{ip1, ip2, ip3}, ","))
 	req.RemoteAddr = "0.0.0.0:3000"
 
-	require.Equal(t, parseUserIP(req), strings.Join([]string{ip1, ip2, ip3, req.RemoteAddr}, ","))
+	require.Equal(t, parseUserIP(req), strings.Join([]string{ip1, ip2, ip3, "0.0.0.0"}, ","))
 }
 
 func TestParseUserIP_RemoteAddrOnly(t *testing.T) {
 	req, err := http.NewRequest("GET", "/teapot", nil)
 	require.Nil(t, err)
 	req.RemoteAddr = "0.0.0.0:3000"
-	require.Equal(t, parseUserIP(req), req.RemoteAddr)
+	require.Equal(t, parseUserIP(req), "0.0.0.0")
 }
 
 func TestParsePreferHeaderWait(t *testing.T) {
diff --git a/cmd/api/src/database/audit.go b/cmd/api/src/database/audit.go
index 3e3f5290d0..8992cd9dd8 100644
--- a/cmd/api/src/database/audit.go
+++ b/cmd/api/src/database/audit.go
@@ -47,6 +47,10 @@ func newAuditLog(context context.Context, entry model.AuditEntry, idResolver aut
 		CommitID:        entry.CommitID,
 	}
 
+	if entry.ErrorMsg != "" {
+		auditLog.Fields["error"] = entry.ErrorMsg
+	}
+
 	authContext := bheCtx.AuthCtx
 	if !authContext.Authenticated() {
 		return auditLog, ErrAuthContextInvalid
@@ -65,10 +69,14 @@ func (s *BloodhoundDB) AppendAuditLog(ctx context.Context, entry model.AuditEntr
 	if auditLog, err := newAuditLog(ctx, entry, s.idResolver); err != nil && err != ErrAuthContextInvalid {
 		return fmt.Errorf("audit log append: %w", err)
 	} else {
-		return CheckError(s.db.Create(&auditLog))
+		return s.CreateAuditLog(auditLog)
 	}
 }
 
+func (s *BloodhoundDB) CreateAuditLog(auditLog model.AuditLog) error {
+	return CheckError(s.db.Create(&auditLog))
+}
+
 func (s *BloodhoundDB) ListAuditLogs(before, after time.Time, offset, limit int, order string, filter model.SQLFilter) (model.AuditLogs, int, error) {
 	var (
 		auditLogs model.AuditLogs
@@ -123,6 +131,7 @@ func (s *BloodhoundDB) AuditableTransaction(ctx context.Context, auditEntry mode
 
 	if err != nil {
 		auditEntry.Status = model.AuditStatusFailure
+		auditEntry.ErrorMsg = err.Error()
 	} else {
 		auditEntry.Status = model.AuditStatusSuccess
 	}
diff --git a/cmd/api/src/database/db.go b/cmd/api/src/database/db.go
index a5b4643fcf..6f98839499 100644
--- a/cmd/api/src/database/db.go
+++ b/cmd/api/src/database/db.go
@@ -82,6 +82,7 @@ type Database interface {
 	RawFirst(value any) error
 	Wipe() error
 	Migrate() error
+	CreateAuditLog(auditLog model.AuditLog) error
 	AppendAuditLog(ctx context.Context, entry model.AuditEntry) error
 	ListAuditLogs(before, after time.Time, offset, limit int, order string, filter model.SQLFilter) (model.AuditLogs, int, error)
 	CreateRole(role model.Role) (model.Role, error)
diff --git a/cmd/api/src/database/mocks/db.go b/cmd/api/src/database/mocks/db.go
index c8320a944b..86cfc70612 100644
--- a/cmd/api/src/database/mocks/db.go
+++ b/cmd/api/src/database/mocks/db.go
@@ -155,6 +155,20 @@ func (mr *MockDatabaseMockRecorder) CreateAssetGroupSelector(arg0, arg1, arg2 in
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "CreateAssetGroupSelector", reflect.TypeOf((*MockDatabase)(nil).CreateAssetGroupSelector), arg0, arg1, arg2)
 }
 
+// CreateAuditLog mocks base method.
+func (m *MockDatabase) CreateAuditLog(arg0 model.AuditLog) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "CreateAuditLog", arg0)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// CreateAuditLog indicates an expected call of CreateAuditLog.
+func (mr *MockDatabaseMockRecorder) CreateAuditLog(arg0 interface{}) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "CreateAuditLog", reflect.TypeOf((*MockDatabase)(nil).CreateAuditLog), arg0)
+}
+
 // CreateAuthSecret mocks base method.
 func (m *MockDatabase) CreateAuthSecret(arg0 context.Context, arg1 model.AuthSecret) (model.AuthSecret, error) {
 	m.ctrl.T.Helper()
diff --git a/packages/go/headers/generate.go b/packages/go/headers/cmd/generate.go
similarity index 100%
rename from packages/go/headers/generate.go
rename to packages/go/headers/cmd/generate.go