diff --git a/pkg/cli/add_package_manifest_imports.go b/pkg/cli/add_package_manifest_imports.go
index 5238639d52a..f2b62d0c710 100644
--- a/pkg/cli/add_package_manifest_imports.go
+++ b/pkg/cli/add_package_manifest_imports.go
@@ -60,6 +60,8 @@ func resolveRepositoryPackageManifestGraph(
 		rootPackagePath = ""
 	}
 
+	addPackageManifestLog.Printf("Resolving package manifest import graph: root=%s", rootPath)
+
 	resolver := &repositoryPackageManifestGraphResolver{
 		rootPackagePath: rootPackagePath,
 		readManifest:    readManifest,
@@ -68,6 +70,7 @@ func resolveRepositoryPackageManifestGraph(
 	if err := resolver.visit(rootPath, root); err != nil {
 		return nil, nil, err
 	}
+	addPackageManifestLog.Printf("Resolved package manifest import graph: %d node(s), %d warning(s)", len(resolver.nodes), len(resolver.warnings))
 	return resolver.nodes, resolver.warnings, nil
 }
 
@@ -82,6 +85,7 @@ func (r *repositoryPackageManifestGraphResolver) visit(manifestPath string, mani
 			}
 		}
 		cycle := append(append([]string{}, r.stack[cycleStart:]...), manifestPath)
+		addPackageManifestLog.Printf("Import cycle detected: %s", strings.Join(cycle, " -> "))
 		return fmt.Errorf("package manifest import cycle detected: %s", strings.Join(cycle, " -> "))
 	case 2:
 		return nil
@@ -198,6 +202,7 @@ func readLocalImportedManifest(manifestPath, packageRoot string) ([]byte, error)
 		return nil, err
 	}
 	if relative == ".." || strings.HasPrefix(relative, ".."+string(os.PathSeparator)) {
+		addPackageManifestLog.Printf("Rejecting imported manifest %q: resolves outside package root %q", manifestPath, packageRoot)
 		return nil, fmt.Errorf("import %q resolves outside the package root", manifestPath)
 	}
 	declaredRelative, err := filepath.Rel(filepath.Clean(packageRoot), filepath.Clean(manifestPath))
diff --git a/pkg/cli/add_project_file.go b/pkg/cli/add_project_file.go
index 8a6f329413d..e7d7e0c9569 100644
--- a/pkg/cli/add_project_file.go
+++ b/pkg/cli/add_project_file.go
@@ -19,10 +19,12 @@ func mergeProjectFileWithTracking(resolved *ResolvedWorkflow, tracker *FileTrack
 	destFile := filepath.Join(gitRoot, workflow.RepoConfigFileName)
 	existing := []byte("{}")
 	fileExists := fileutil.FileExists(destFile)
+	addLog.Printf("Merging package project file: dest=%s, exists=%t", destFile, fileExists)
 	if err := fileutil.ValidatePathWithinBase(gitRoot, destFile); err != nil {
 		return fmt.Errorf("failed to validate project file destination %q: %w", workflow.RepoConfigFileName, err)
 	}
 	if info, err := os.Lstat(destFile); err == nil && info.Mode()&os.ModeSymlink != 0 {
+		addLog.Printf("Refusing to merge project file %q: destination is a symbolic link", destFile)
 		return fmt.Errorf("project file destination %q is a symbolic link, which is not allowed", workflow.RepoConfigFileName)
 	}
 	if fileExists {
@@ -61,6 +63,7 @@ func mergeProjectFileWithTracking(resolved *ResolvedWorkflow, tracker *FileTrack
 	if err := os.WriteFile(destFile, merged, constants.FilePermPublic); err != nil {
 		return fmt.Errorf("failed to write project file %q: %w", workflow.RepoConfigFileName, err)
 	}
+	addLog.Printf("Wrote merged project file: dest=%s, size=%d bytes", destFile, len(merged))
 	return nil
 }