diff --git a/.github/workflows/cloclo.lock.yml b/.github/workflows/cloclo.lock.yml
index 19929dd7e0..ec6d72d786 100644
--- a/.github/workflows/cloclo.lock.yml
+++ b/.github/workflows/cloclo.lock.yml
@@ -723,20 +723,20 @@ jobs:
           __GH_AW_NEEDS_ACTIVATION_OUTPUTS_TEXT__
           ```
           
-          {{#if ${{ github.event.issue.number }} }}
+          {{#if __GH_AW_GITHUB_EVENT_ISSUE_NUMBER__ }}
           ## Issue Context
           
           - **Issue Number**: __GH_AW_GITHUB_EVENT_ISSUE_NUMBER__
           - **Issue State**: __GH_AW_GITHUB_EVENT_ISSUE_STATE__
           {{/if}}
           
-          {{#if ${{ github.event.discussion.number }} }}
+          {{#if __GH_AW_GITHUB_EVENT_DISCUSSION_NUMBER__ }}
           ## Discussion Context
           
           - **Discussion Number**: __GH_AW_GITHUB_EVENT_DISCUSSION_NUMBER__
           {{/if}}
           
-          {{#if ${{ github.event.pull_request.number }} }}
+          {{#if __GH_AW_GITHUB_EVENT_PULL_REQUEST_NUMBER__ }}
           ## Pull Request Context
           
           **IMPORTANT**: If this command was triggered from a pull request, you must capture and include the PR branch information in your processing:
diff --git a/pkg/workflow/compiler_yaml.go b/pkg/workflow/compiler_yaml.go
index 93897ebacf..f03c1b9717 100644
--- a/pkg/workflow/compiler_yaml.go
+++ b/pkg/workflow/compiler_yaml.go
@@ -183,6 +183,11 @@ func (c *Compiler) generatePrompt(yaml *strings.Builder, data *WorkflowData) {
 		cleanedMarkdownContent = SubstituteImportInputs(cleanedMarkdownContent, data.ImportInputs)
 	}
 
+	// Wrap GitHub expressions in template conditionals BEFORE extracting expressions
+	// This ensures that expressions created by wrapping (e.g., {{#if ${{ expr }} }})
+	// are also extracted and replaced with environment variables
+	cleanedMarkdownContent = wrapExpressionsInTemplateConditionals(cleanedMarkdownContent)
+
 	// Extract expressions and create environment variable mappings for security
 	extractor := NewExpressionExtractor()
 	expressionMappings, err := extractor.ExtractExpressions(cleanedMarkdownContent)
@@ -197,9 +202,6 @@ func (c *Compiler) generatePrompt(yaml *strings.Builder, data *WorkflowData) {
 		cleanedMarkdownContent = extractor.ReplaceExpressionsWithEnvVars(cleanedMarkdownContent)
 	}
 
-	// Wrap GitHub expressions in template conditionals
-	cleanedMarkdownContent = wrapExpressionsInTemplateConditionals(cleanedMarkdownContent)
-
 	// Split content into manageable chunks
 	chunks := splitContentIntoChunks(cleanedMarkdownContent)
 	compilerYamlLog.Printf("Split prompt into %d chunks", len(chunks))
diff --git a/pkg/workflow/template_expression_integration_test.go b/pkg/workflow/template_expression_integration_test.go
index 3119658821..f530d38fa1 100644
--- a/pkg/workflow/template_expression_integration_test.go
+++ b/pkg/workflow/template_expression_integration_test.go
@@ -91,16 +91,17 @@ ${{ needs.activation.outputs.text }}
 		t.Error("Compiled workflow should contain interpolation and template rendering step")
 	}
 
-	// Verify GitHub expressions are properly wrapped in template conditionals
-	expectedWrappedExpressions := []string{
-		"{{#if ${{ github.event.issue.number }} }}",
-		"{{#if ${{ github.event.pull_request.number }} }}",
-		"{{#if ${{ needs.activation.outputs.text }} }}",
+	// Verify GitHub expressions are properly replaced with placeholders in template conditionals
+	// After the fix, expressions should be replaced with __GH_AW_*__ placeholders
+	expectedPlaceholderExpressions := []string{
+		"{{#if __GH_AW_GITHUB_EVENT_ISSUE_NUMBER__ }}",
+		"{{#if __GH_AW_GITHUB_EVENT_PULL_REQUEST_NUMBER__ }}",
+		"{{#if __GH_AW_NEEDS_ACTIVATION_OUTPUTS_TEXT__ }}",
 	}
 
-	for _, expectedExpr := range expectedWrappedExpressions {
+	for _, expectedExpr := range expectedPlaceholderExpressions {
 		if !strings.Contains(compiledStr, expectedExpr) {
-			t.Errorf("Compiled workflow should contain wrapped expression: %s", expectedExpr)
+			t.Errorf("Compiled workflow should contain placeholder expression: %s", expectedExpr)
 		}
 	}
 
@@ -266,25 +267,27 @@ Steps expression - will be wrapped.
 
 	compiledStr := string(compiledYAML)
 
-	// Verify all expressions are wrapped (simplified behavior)
-	if !strings.Contains(compiledStr, "{{#if ${{ github.event.issue.number }} }}") {
-		t.Error("GitHub expression should be wrapped")
+	// Verify all expressions are replaced with placeholders (correct behavior)
+	if !strings.Contains(compiledStr, "{{#if __GH_AW_GITHUB_EVENT_ISSUE_NUMBER__ }}") {
+		t.Error("GitHub expression should be replaced with placeholder")
 	}
 
-	if !strings.Contains(compiledStr, "{{#if ${{ steps.my_step.outputs.value }} }}") {
-		t.Error("Steps expression should be wrapped")
+	if !strings.Contains(compiledStr, "{{#if __GH_AW_STEPS_MY_STEP_OUTPUTS_VALUE__ }}") {
+		t.Error("Steps expression should be replaced with placeholder")
 	}
 
-	if !strings.Contains(compiledStr, "{{#if ${{ true }} }}") {
-		t.Error("Literal 'true' should be wrapped")
+	// Verify that literal values are also replaced with placeholders
+	// true and false literals get normalized to __GH_AW_TRUE__ and __GH_AW_FALSE__
+	if !strings.Contains(compiledStr, "{{#if __GH_AW_TRUE__ }}") {
+		t.Error("Literal 'true' should be replaced with placeholder")
 	}
 
-	if !strings.Contains(compiledStr, "{{#if ${{ false }} }}") {
-		t.Error("Literal 'false' should be wrapped")
+	if !strings.Contains(compiledStr, "{{#if __GH_AW_FALSE__ }}") {
+		t.Error("Literal 'false' should be replaced with placeholder")
 	}
 
-	if !strings.Contains(compiledStr, "{{#if ${{ some_variable }} }}") {
-		t.Error("Unknown variable should be wrapped")
+	if !strings.Contains(compiledStr, "{{#if __GH_AW_SOME_VARIABLE__ }}") {
+		t.Error("Unknown variable should be replaced with placeholder")
 	}
 
 	// Make sure we didn't create invalid double-wrapping
diff --git a/pkg/workflow/template_rendering_test.go b/pkg/workflow/template_rendering_test.go
index 77c463b892..5316b64576 100644
--- a/pkg/workflow/template_rendering_test.go
+++ b/pkg/workflow/template_rendering_test.go
@@ -77,22 +77,23 @@ Normal content here.
 		t.Error("Interpolation and template rendering step should use github-script action")
 	}
 
-	// Verify that GitHub expressions are wrapped in ${{ }}
-	if !strings.Contains(compiledStr, "{{#if ${{ github.event.issue.number }} }}") {
-		t.Error("Compiled workflow should contain wrapped github.event.issue.number expression")
+	// Verify that GitHub expressions are replaced with placeholders
+	if !strings.Contains(compiledStr, "{{#if __GH_AW_GITHUB_EVENT_ISSUE_NUMBER__ }}") {
+		t.Error("Compiled workflow should contain placeholder for github.event.issue.number expression")
 	}
 
-	if !strings.Contains(compiledStr, "{{#if ${{ github.actor }} }}") {
-		t.Error("Compiled workflow should contain wrapped github.actor expression")
+	if !strings.Contains(compiledStr, "{{#if __GH_AW_GITHUB_ACTOR__ }}") {
+		t.Error("Compiled workflow should contain placeholder for github.actor expression")
 	}
 
-	// Verify that literal values are also wrapped (simplified behavior)
-	if !strings.Contains(compiledStr, "{{#if ${{ true }} }}") {
-		t.Error("Compiled workflow should contain wrapped literal true")
+	// Verify that literal values are also replaced with placeholders
+	// true and false literals get normalized to __GH_AW_TRUE__ and __GH_AW_FALSE__
+	if !strings.Contains(compiledStr, "{{#if __GH_AW_TRUE__ }}") {
+		t.Error("Compiled workflow should contain placeholder for literal true")
 	}
 
-	if !strings.Contains(compiledStr, "{{#if ${{ false }} }}") {
-		t.Error("Compiled workflow should contain wrapped literal false")
+	if !strings.Contains(compiledStr, "{{#if __GH_AW_FALSE__ }}") {
+		t.Error("Compiled workflow should contain placeholder for literal false")
 	}
 
 	// Verify the setupGlobals helper is used