diff --git a/app/cli/lib/context_load.go b/app/cli/lib/context_load.go
index 345fd443..ba95d8e2 100644
--- a/app/cli/lib/context_load.go
+++ b/app/cli/lib/context_load.go
@@ -12,6 +12,7 @@ import (
 	"plandex/term"
 	"plandex/types"
 	"plandex/url"
+	"plandex/utils"
 	"strings"
 	"sync"
 
@@ -87,6 +88,7 @@ func MustLoadContext(resources []string, params *types.LoadContextParams) {
 					resource = resource[2:]
 				}
 
+				resource = utils.EnsureValidPath(resource)
 				inputFilePaths = append(inputFilePaths, resource)
 			}
 		}
diff --git a/app/cli/utils/utils.go b/app/cli/utils/utils.go
index 346500bb..9e6f1bb1 100644
--- a/app/cli/utils/utils.go
+++ b/app/cli/utils/utils.go
@@ -10,3 +10,12 @@ func EnsureMinDuration(start time.Time, minDuration time.Duration) {
 		time.Sleep(minDuration - elapsed)
 	}
 }
+
+func EnsureValidPath(path string) string {
+	// Remove trailing slash if it's not the root path
+	if len(path) > 1 && path[len(path)-1] == '/' {
+		path = path[:len(path)-1]
+	}
+
+	return path
+}
diff --git a/app/cli/utils/utils_test.go b/app/cli/utils/utils_test.go
new file mode 100644
index 00000000..a5127f31
--- /dev/null
+++ b/app/cli/utils/utils_test.go
@@ -0,0 +1,25 @@
+package utils
+
+import (
+	"testing"
+)
+
+func TestEnsureValidPath(t *testing.T) {
+	tests := []struct {
+		input    string
+		expected string
+	}{
+		{"/home/user/", "/home/user"},
+		{"/", "/"},
+	}
+
+	for _, test := range tests {
+		t.Run("Path: "+test.input, func(t *testing.T) {
+			output := EnsureValidPath(test.input)
+			// t.Logf(output)
+			if output != test.expected {
+				t.Errorf("EnsureValidPath(%q) = %q; want %q", test.input, output, test.expected)
+			}
+		})
+	}
+}