diff --git a/server/internal/context/context.go b/server/internal/context/context.go
index dda7eeb..e40353a 100644
--- a/server/internal/context/context.go
+++ b/server/internal/context/context.go
@@ -5,6 +5,7 @@ import (
 	"context"
 	"fmt"
 	"net/http"
+	"novamd/internal/logging"
 	"novamd/internal/models"
 )
 
@@ -28,10 +29,22 @@ type HandlerContext struct {
 	Workspace *models.Workspace // Optional, only set for workspace routes
 }
 
+var logger logging.Logger
+
+func getLogger() logging.Logger {
+	if logger == nil {
+		logger = logging.WithGroup("context")
+	}
+	return logger
+}
+
 // GetRequestContext retrieves the handler context from the request
 func GetRequestContext(w http.ResponseWriter, r *http.Request) (*HandlerContext, bool) {
 	ctx := r.Context().Value(HandlerContextKey)
 	if ctx == nil {
+		getLogger().Error("missing handler context in request",
+			"path", r.URL.Path,
+			"method", r.Method)
 		http.Error(w, "Internal server error", http.StatusInternalServerError)
 		return nil, false
 	}
diff --git a/server/internal/context/middleware.go b/server/internal/context/middleware.go
index c916e96..a079eff 100644
--- a/server/internal/context/middleware.go
+++ b/server/internal/context/middleware.go
@@ -13,6 +13,9 @@ func WithUserContextMiddleware(next http.Handler) http.Handler {
 	return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		claims, err := GetUserFromContext(r.Context())
 		if err != nil {
+			getLogger().Error("failed to get user from context",
+				"error", err,
+				"path", r.URL.Path)
 			http.Error(w, "Unauthorized", http.StatusUnauthorized)
 			return
 		}
@@ -22,6 +25,11 @@ func WithUserContextMiddleware(next http.Handler) http.Handler {
 			UserRole: claims.Role,
 		}
 
+		getLogger().Debug("user context extracted from claims",
+			"userID", claims.UserID,
+			"role", claims.Role,
+			"path", r.URL.Path)
+
 		r = WithHandlerContext(r, hctx)
 		next.ServeHTTP(w, r)
 	})
@@ -39,11 +47,21 @@ func WithWorkspaceContextMiddleware(db db.WorkspaceReader) func(http.Handler) ht
 			workspaceName := chi.URLParam(r, "workspaceName")
 			workspace, err := db.GetWorkspaceByName(ctx.UserID, workspaceName)
 			if err != nil {
-				http.Error(w, "Workspace not found", http.StatusNotFound)
+				getLogger().Error("failed to get workspace",
+					"error", err,
+					"userID", ctx.UserID,
+					"workspace", workspaceName,
+					"path", r.URL.Path)
+				http.Error(w, "Failed to get workspace", http.StatusNotFound)
 				return
 			}
 
-			// Update existing context with workspace
+			getLogger().Debug("workspace context added",
+				"userID", ctx.UserID,
+				"workspaceID", workspace.ID,
+				"workspaceName", workspace.Name,
+				"path", r.URL.Path)
+
 			ctx.Workspace = workspace
 			r = WithHandlerContext(r, ctx)
 			next.ServeHTTP(w, r)