diff --git a/pkg/cli/validators.go b/pkg/cli/validators.go
index 9e24f75db7..8363269f53 100644
--- a/pkg/cli/validators.go
+++ b/pkg/cli/validators.go
@@ -4,20 +4,28 @@ import (
 	"errors"
 	"regexp"
 	"strings"
+
+	"github.com/githubnext/gh-aw/pkg/logger"
 )
 
+var validatorsLog = logger.New("cli:validators")
+
 // workflowNameRegex validates workflow names contain only alphanumeric characters, hyphens, and underscores
 var workflowNameRegex = regexp.MustCompile(`^[a-zA-Z0-9_-]+$`)
 
 // ValidateWorkflowName checks if the provided workflow name is valid.
 // It ensures the name is not empty and contains only alphanumeric characters, hyphens, and underscores.
 func ValidateWorkflowName(s string) error {
+	validatorsLog.Printf("Validating workflow name: %s", s)
 	if s == "" {
+		validatorsLog.Print("Workflow name validation failed: empty name")
 		return errors.New("workflow name cannot be empty")
 	}
 	if !workflowNameRegex.MatchString(s) {
+		validatorsLog.Printf("Workflow name validation failed: invalid characters in %s", s)
 		return errors.New("workflow name must contain only alphanumeric characters, hyphens, and underscores")
 	}
+	validatorsLog.Printf("Workflow name validated successfully: %s", s)
 	return nil
 }
 
@@ -25,12 +33,16 @@ func ValidateWorkflowName(s string) error {
 // It ensures the intent has meaningful content with at least 20 characters
 // and is not just whitespace.
 func ValidateWorkflowIntent(s string) error {
+	validatorsLog.Printf("Validating workflow intent: length=%d", len(s))
 	trimmed := strings.TrimSpace(s)
 	if len(trimmed) == 0 {
+		validatorsLog.Print("Workflow intent validation failed: empty content")
 		return errors.New("workflow instructions cannot be empty")
 	}
 	if len(trimmed) < 20 {
+		validatorsLog.Printf("Workflow intent validation failed: too short (%d chars)", len(trimmed))
 		return errors.New("please provide at least 20 characters of instructions")
 	}
+	validatorsLog.Printf("Workflow intent validated successfully: %d chars", len(trimmed))
 	return nil
 }
diff --git a/pkg/gitutil/gitutil.go b/pkg/gitutil/gitutil.go
index 1224f321cd..4536b1e3f2 100644
--- a/pkg/gitutil/gitutil.go
+++ b/pkg/gitutil/gitutil.go
@@ -1,18 +1,29 @@
 package gitutil
 
-import "strings"
+import (
+	"strings"
+
+	"github.com/githubnext/gh-aw/pkg/logger"
+)
+
+var log = logger.New("gitutil:gitutil")
 
 // IsAuthError checks if an error message indicates an authentication issue.
 // This is used to detect when GitHub API calls fail due to missing or invalid credentials.
 func IsAuthError(errMsg string) bool {
+	log.Printf("Checking if error is auth-related: %s", errMsg)
 	lowerMsg := strings.ToLower(errMsg)
-	return strings.Contains(lowerMsg, "gh_token") ||
+	isAuth := strings.Contains(lowerMsg, "gh_token") ||
 		strings.Contains(lowerMsg, "github_token") ||
 		strings.Contains(lowerMsg, "authentication") ||
 		strings.Contains(lowerMsg, "not logged into") ||
 		strings.Contains(lowerMsg, "unauthorized") ||
 		strings.Contains(lowerMsg, "forbidden") ||
 		strings.Contains(lowerMsg, "permission denied")
+	if isAuth {
+		log.Print("Detected authentication error")
+	}
+	return isAuth
 }
 
 // IsHexString checks if a string contains only hexadecimal characters.
diff --git a/pkg/repoutil/repoutil.go b/pkg/repoutil/repoutil.go
index a6e886c5f6..fd67f61eba 100644
--- a/pkg/repoutil/repoutil.go
+++ b/pkg/repoutil/repoutil.go
@@ -4,33 +4,44 @@ package repoutil
 import (
 	"fmt"
 	"strings"
+
+	"github.com/githubnext/gh-aw/pkg/logger"
 )
 
+var log = logger.New("repoutil:repoutil")
+
 // SplitRepoSlug splits a repository slug (owner/repo) into owner and repo parts.
 // Returns an error if the slug format is invalid.
 func SplitRepoSlug(slug string) (owner, repo string, err error) {
+	log.Printf("Splitting repo slug: %s", slug)
 	parts := strings.Split(slug, "/")
 	if len(parts) != 2 || parts[0] == "" || parts[1] == "" {
+		log.Printf("Invalid repo slug format: %s", slug)
 		return "", "", fmt.Errorf("invalid repo format: %s", slug)
 	}
+	log.Printf("Split result: owner=%s, repo=%s", parts[0], parts[1])
 	return parts[0], parts[1], nil
 }
 
 // ParseGitHubURL extracts the owner and repo from a GitHub URL.
 // Handles both SSH (git@github.com:owner/repo.git) and HTTPS (https://github.com/owner/repo.git) formats.
 func ParseGitHubURL(url string) (owner, repo string, err error) {
+	log.Printf("Parsing GitHub URL: %s", url)
 	var repoPath string
 
 	// SSH format: git@github.com:owner/repo.git
 	if strings.HasPrefix(url, "git@github.com:") {
 		repoPath = strings.TrimPrefix(url, "git@github.com:")
+		log.Printf("Detected SSH format, extracted path: %s", repoPath)
 	} else if strings.Contains(url, "github.com/") {
 		// HTTPS format: https://github.com/owner/repo.git
 		parts := strings.Split(url, "github.com/")
 		if len(parts) >= 2 {
 			repoPath = parts[1]
+			log.Printf("Detected HTTPS format, extracted path: %s", repoPath)
 		}
 	} else {
+		log.Printf("URL does not match known GitHub formats: %s", url)
 		return "", "", fmt.Errorf("URL does not appear to be a GitHub repository: %s", url)
 	}
 
diff --git a/pkg/workflow/github_tool_to_toolset.go b/pkg/workflow/github_tool_to_toolset.go
index 6664749b05..fefe2dbfa7 100644
--- a/pkg/workflow/github_tool_to_toolset.go
+++ b/pkg/workflow/github_tool_to_toolset.go
@@ -3,8 +3,12 @@ package workflow
 import (
 	_ "embed"
 	"encoding/json"
+
+	"github.com/githubnext/gh-aw/pkg/logger"
 )
 
+var githubToolToToolsetLog = logger.New("workflow:github_tool_to_toolset")
+
 //go:embed data/github_tool_to_toolset.json
 var githubToolToToolsetJSON []byte
 
@@ -23,7 +27,10 @@ func init() {
 // ValidateGitHubToolsAgainstToolsets validates that all allowed GitHub tools have their
 // corresponding toolsets enabled in the configuration
 func ValidateGitHubToolsAgainstToolsets(allowedTools []string, enabledToolsets []string) error {
+	githubToolToToolsetLog.Printf("Validating GitHub tools against toolsets: allowed_tools=%d, enabled_toolsets=%d", len(allowedTools), len(enabledToolsets))
+
 	if len(allowedTools) == 0 {
+		githubToolToToolsetLog.Print("No tools to validate, skipping")
 		// No specific tools restricted, validation not needed
 		return nil
 	}
@@ -33,6 +40,7 @@ func ValidateGitHubToolsAgainstToolsets(allowedTools []string, enabledToolsets [
 	for _, toolset := range enabledToolsets {
 		enabledSet[toolset] = true
 	}
+	githubToolToToolsetLog.Printf("Enabled toolsets: %v", enabledToolsets)
 
 	// Track missing toolsets and which tools need them
 	missingToolsets := make(map[string][]string) // toolset -> list of tools that need it
@@ -40,19 +48,23 @@ func ValidateGitHubToolsAgainstToolsets(allowedTools []string, enabledToolsets [
 	for _, tool := range allowedTools {
 		requiredToolset, exists := GitHubToolToToolsetMap[tool]
 		if !exists {
+			githubToolToToolsetLog.Printf("Tool %s not found in mapping, skipping validation", tool)
 			// Tool not in our mapping - this could be a new tool or a typo
 			// We'll skip validation for unknown tools to avoid false positives
 			continue
 		}
 
 		if !enabledSet[requiredToolset] {
+			githubToolToToolsetLog.Printf("Tool %s requires missing toolset: %s", tool, requiredToolset)
 			missingToolsets[requiredToolset] = append(missingToolsets[requiredToolset], tool)
 		}
 	}
 
 	if len(missingToolsets) > 0 {
+		githubToolToToolsetLog.Printf("Validation failed: missing %d toolsets", len(missingToolsets))
 		return NewGitHubToolsetValidationError(missingToolsets)
 	}
 
+	githubToolToToolsetLog.Print("Validation successful: all tools have required toolsets")
 	return nil
 }
diff --git a/pkg/workflow/prompts.go b/pkg/workflow/prompts.go
index ed02fae95e..82e3732f7d 100644
--- a/pkg/workflow/prompts.go
+++ b/pkg/workflow/prompts.go
@@ -21,9 +21,12 @@ import (
 // hasPlaywrightTool checks if the playwright tool is enabled in the tools configuration
 func hasPlaywrightTool(parsedTools *Tools) bool {
 	if parsedTools == nil {
+		log.Print("Checking for Playwright tool: no parsed tools provided")
 		return false
 	}
-	return parsedTools.Playwright != nil
+	hasPlaywright := parsedTools.Playwright != nil
+	log.Printf("Playwright tool enabled: %v", hasPlaywright)
+	return hasPlaywright
 }
 
 // ============================================================================
@@ -32,12 +35,16 @@ func hasPlaywrightTool(parsedTools *Tools) bool {
 
 // hasCommentRelatedTriggers checks if the workflow has any comment-related event triggers
 func (c *Compiler) hasCommentRelatedTriggers(data *WorkflowData) bool {
+	log.Printf("Checking for comment-related triggers: command_count=%d, on=%s", len(data.Command), data.On)
+
 	// Check for command trigger (which expands to comment events)
 	if len(data.Command) > 0 {
+		log.Print("Found command trigger, enabling comment-related features")
 		return true
 	}
 
 	if data.On == "" {
+		log.Print("No 'on' trigger defined")
 		return false
 	}
 
@@ -45,9 +52,11 @@ func (c *Compiler) hasCommentRelatedTriggers(data *WorkflowData) bool {
 	commentEvents := []string{"issue_comment", "pull_request_review_comment", "pull_request_review"}
 	for _, event := range commentEvents {
 		if strings.Contains(data.On, event) {
+			log.Printf("Found comment-related event trigger: %s", event)
 			return true
 		}
 	}
 
+	log.Print("No comment-related triggers found")
 	return false
 }