diff --git a/pkg/cli/helpers.go b/pkg/cli/helpers.go
index 980a0f812f8..4019067a03a 100644
--- a/pkg/cli/helpers.go
+++ b/pkg/cli/helpers.go
@@ -4,9 +4,12 @@ import (
 	"os"
 	"strings"
 
+	"github.com/github/gh-aw/pkg/logger"
 	"github.com/github/gh-aw/pkg/parser"
 )
 
+var helpersLog = logger.New("cli:helpers")
+
 // getParentDir returns the directory part of a path
 func getParentDir(path string) string {
 	idx := strings.LastIndex(path, "/")
@@ -20,8 +23,10 @@ func getParentDir(path string) string {
 // and returns the "owner/repo" portion (e.g. "github/gh-aw"). Returns "" if the file
 // cannot be read, has no source field, or the field is not in the expected format.
 func readSourceRepoFromFile(path string) string {
+	helpersLog.Printf("Reading source repo from file: %s", path)
 	content, err := os.ReadFile(path)
 	if err != nil {
+		helpersLog.Printf("Failed to read file: %s", err)
 		return ""
 	}
 	result, err := parser.ExtractFrontmatterFromContent(string(content))
@@ -41,7 +46,9 @@ func readSourceRepoFromFile(path string) string {
 	if len(slashParts) < 2 {
 		return ""
 	}
-	return slashParts[0] + "/" + slashParts[1]
+	repo := slashParts[0] + "/" + slashParts[1]
+	helpersLog.Printf("Extracted source repo: %s", repo)
+	return repo
 }
 
 // sourceRepoLabel returns the source repo string for display in error messages.
diff --git a/pkg/cli/trial_confirmation.go b/pkg/cli/trial_confirmation.go
index d0d84e95750..112860f8da1 100644
--- a/pkg/cli/trial_confirmation.go
+++ b/pkg/cli/trial_confirmation.go
@@ -7,12 +7,16 @@ import (
 	"strings"
 
 	"github.com/github/gh-aw/pkg/console"
+	"github.com/github/gh-aw/pkg/logger"
 	"github.com/github/gh-aw/pkg/sliceutil"
 	"github.com/github/gh-aw/pkg/workflow"
 )
 
+var trialConfirmationLog = logger.New("cli:trial_confirmation")
+
 // showTrialConfirmation displays a confirmation prompt to the user using parsed workflow specs
 func showTrialConfirmation(parsedSpecs []*WorkflowSpec, logicalRepoSlug, cloneRepoSlug, hostRepoSlug string, deleteHostRepo bool, forceDeleteHostRepo bool, autoMergePRs bool, repeatCount int, directTrialMode bool, engineOverride string) error {
+	trialConfirmationLog.Printf("Showing trial confirmation: workflows=%d, hostRepo=%s, cloneRepo=%s, repeat=%d, directMode=%v", len(parsedSpecs), hostRepoSlug, cloneRepoSlug, repeatCount, directTrialMode)
 	githubHost := getGitHubHost()
 	hostRepoSlugURL := fmt.Sprintf("%s/%s", githubHost, hostRepoSlug)
 
@@ -109,6 +113,7 @@ func showTrialConfirmation(parsedSpecs []*WorkflowSpec, logicalRepoSlug, cloneRe
 	if err := checkCmd.Run(); err == nil {
 		hostRepoExists = true
 	}
+	trialConfirmationLog.Printf("Host repo check: exists=%v, forceDelete=%v", hostRepoExists, forceDeleteHostRepo)
 
 	// Step 1: Repository creation/reuse
 	stepNum := 1
@@ -213,8 +218,10 @@ func showTrialConfirmation(parsedSpecs []*WorkflowSpec, logicalRepoSlug, cloneRe
 	}
 
 	if !confirmed {
+		trialConfirmationLog.Print("Trial cancelled by user")
 		return errors.New("trial cancelled by user")
 	}
 
+	trialConfirmationLog.Print("Trial confirmed by user, proceeding")
 	return nil
 }
diff --git a/pkg/workflow/compiler_yaml_step_conversion.go b/pkg/workflow/compiler_yaml_step_conversion.go
index e075417876f..02860a3236f 100644
--- a/pkg/workflow/compiler_yaml_step_conversion.go
+++ b/pkg/workflow/compiler_yaml_step_conversion.go
@@ -6,12 +6,16 @@ import (
 	"strings"
 
 	"github.com/github/gh-aw/pkg/constants"
+	"github.com/github/gh-aw/pkg/logger"
 	"github.com/goccy/go-yaml"
 )
 
+var stepConversionLog = logger.New("workflow:compiler_yaml_step_conversion")
+
 // ConvertStepToYAML converts a step map to YAML string with proper indentation.
 // This is a shared utility function used by all engines and the compiler.
 func ConvertStepToYAML(stepMap map[string]any) (string, error) {
+	stepConversionLog.Printf("Converting step to YAML: fields=%d", len(stepMap))
 	// Use OrderMapFields to get ordered MapSlice
 	orderedStep := OrderMapFields(stepMap, constants.PriorityStepFields)
 
@@ -40,6 +44,7 @@ func ConvertStepToYAML(stepMap map[string]any) (string, error) {
 		}
 	}
 
+	stepConversionLog.Printf("Step conversion complete: %d lines generated", len(lines))
 	return result.String(), nil
 }
 
@@ -95,6 +100,8 @@ func unquoteUsesWithComments(yamlStr string) string {
 
 // renderStepFromMap renders a GitHub Actions step from a map to YAML
 func (c *Compiler) renderStepFromMap(yaml *strings.Builder, step map[string]any, data *WorkflowData, indent string) {
+	stepName, _ := step["name"].(string)
+	stepConversionLog.Printf("Rendering step from map: name=%q, fields=%d", stepName, len(step))
 	// Start the step with a dash
 	yaml.WriteString(indent + "- ")
 
diff --git a/pkg/workflow/playwright_tools.go b/pkg/workflow/playwright_tools.go
index a72d765b682..3a5ade8661a 100644
--- a/pkg/workflow/playwright_tools.go
+++ b/pkg/workflow/playwright_tools.go
@@ -1,5 +1,9 @@
 package workflow
 
+import "github.com/github/gh-aw/pkg/logger"
+
+var playwrightToolsLog = logger.New("workflow:playwright_tools")
+
 // GetPlaywrightTools returns the list of Playwright browser tool names available in the
 // copilot agent MCP server configuration.
 // This is a shared function used by all engines for consistent Playwright tool configuration.
@@ -33,5 +37,6 @@ func GetPlaywrightTools() []any {
 	for i, tool := range tools {
 		result[i] = tool
 	}
+	playwrightToolsLog.Printf("Returning %d Playwright tools", len(result))
 	return result
 }