diff --git a/cmd/server/main.go b/cmd/server/main.go
index 6b6d04b..58998ca 100644
--- a/cmd/server/main.go
+++ b/cmd/server/main.go
@@ -12,6 +12,7 @@ import (
 
 	"github.com/kyren223/eko/internal/server"
 	"github.com/kyren223/eko/internal/server/api"
+	"github.com/kyren223/eko/internal/server/ctxkeys"
 	"github.com/kyren223/eko/pkg/assert"
 	"gopkg.in/natefinch/lumberjack.v2"
 )
@@ -27,6 +28,8 @@ func main() {
 
 	setupLogging()
 
+	log.Println("Debugging prod", "prod", prod)
+
 	api.ConnectToDatabase()
 	assert.AddFlush(api.DB())
 	defer api.DB().Close()
@@ -68,10 +71,11 @@ func setupLogging() {
 	if prod {
 		level = slog.LevelInfo
 	}
-	handler := slog.NewJSONHandler(rotator, &slog.HandlerOptions{
+	baseHandler := slog.NewJSONHandler(rotator, &slog.HandlerOptions{
 		AddSource: true,
 		Level:     level,
 	})
+	handler := ctxkeys.WrapLogHandler(baseHandler)
 
 	logger := slog.New(handler)
 	slog.SetDefault(logger)
diff --git a/internal/server/ctxkeys/ctxkeys.go b/internal/server/ctxkeys/ctxkeys.go
new file mode 100644
index 0000000..c0f688d
--- /dev/null
+++ b/internal/server/ctxkeys/ctxkeys.go
@@ -0,0 +1,51 @@
+package ctxkeys
+
+import (
+	"context"
+	"log/slog"
+
+	"github.com/kyren223/eko/pkg/assert"
+)
+
+type key int
+
+const (
+	UserID key = iota
+	IpAddr
+	KeyMax
+)
+
+var keyNames = map[key]string{
+	UserID: "user_id",
+	IpAddr: "ip_addr",
+}
+
+func Init() {
+	assert.Assert(len(keyNames) == int(KeyMax), "Keys in keyNames mismatch amount of keys", "len(keyNames)", len(keyNames), "KeyMax", int(KeyMax))
+}
+
+func WithValue(ctx context.Context, k key, v any) context.Context {
+	return context.WithValue(ctx, k, v)
+}
+
+func Value(ctx context.Context, k key) any {
+	return ctx.Value(k)
+}
+
+type ContextHandler struct {
+	slog.Handler
+}
+
+func WrapLogHandler(baseHandler slog.Handler) *ContextHandler {
+	return &ContextHandler{Handler: baseHandler}
+}
+
+func (h *ContextHandler) Handle(ctx context.Context, r slog.Record) error {
+	for k := key(0); k < KeyMax; k++ {
+		if v := Value(ctx, k); v != nil {
+			r.AddAttrs(slog.Any(keyNames[k], v))
+		}
+	}
+
+	return h.Handler.Handle(ctx, r)
+}
diff --git a/internal/server/server.go b/internal/server/server.go
index 8067a19..8accb14 100644
--- a/internal/server/server.go
+++ b/internal/server/server.go
@@ -19,6 +19,7 @@ import (
 	"github.com/kyren223/eko/certs"
 	"github.com/kyren223/eko/internal/packet"
 	"github.com/kyren223/eko/internal/server/api"
+	"github.com/kyren223/eko/internal/server/ctxkeys"
 	"github.com/kyren223/eko/internal/server/session"
 	"github.com/kyren223/eko/pkg/assert"
 	"github.com/kyren223/eko/pkg/snowflake"
@@ -151,6 +152,7 @@ func (server *server) handleConnection(conn net.Conn) {
 	log.Println(addr, "accepted")
 
 	initialCtx, initialCancel := context.WithTimeout(server.ctx, 5*time.Second)
+	initialCtx = context.WithValue(initialCtx, ctxkeys.IpAddr, addr)
 	deadline, _ := initialCtx.Deadline()
 	err := conn.SetDeadline(deadline)
 	assert.NoError(err, "setting read deadline should not error")
@@ -175,8 +177,13 @@ func (server *server) handleConnection(conn net.Conn) {
 		log.Println(addr, "disconnected")
 		return
 	}
+
 	ctx, cancel := context.WithCancel(server.ctx)
 	defer cancel()
+
+	ctx = context.WithValue(ctx, ctxkeys.UserID, user.ID)
+	ctx = context.WithValue(ctx, ctxkeys.IpAddr, addr)
+
 	sess := session.NewSession(server, addr, cancel, user.ID, pubKey)
 	server.AddSession(sess)
 	framer := packet.NewFramer()
diff --git a/terminology.md b/terminology.md
index 50d4cfa..b4332c2 100644
--- a/terminology.md
+++ b/terminology.md
@@ -6,6 +6,8 @@ TODO
 
 ID - A snowflake ID, a snowflake ID is a unique identifier used across the client and server, it embeds metadata including the date it was generated which can be retrieved for display purposes.
 
+User ID - A snowflake ID for a user, used as the primary way to refer to a user in a unique way (like opening a signal with a user)
+
 Receiver ID - usually refers to the "other" person's ID in a 1:1 messaging, but can also refer to the literal `receiver_id` SQL field on the `messages` table which may be either the "other" person, or the user itself.
 
 Frequency ID