diff --git a/pkg/workflow/compiler.go b/pkg/workflow/compiler.go
index 37caf1d84bc..50d26961523 100644
--- a/pkg/workflow/compiler.go
+++ b/pkg/workflow/compiler.go
@@ -177,6 +177,12 @@ func (c *Compiler) validateWorkflowData(workflowData *WorkflowData, markdownPath
 		return formatCompilerError(markdownPath, "error", err.Error(), err)
 	}
 
+	// Validate safe-outputs max configuration
+	log.Printf("Validating safe-outputs max fields")
+	if err := validateSafeOutputsMax(workflowData.SafeOutputs); err != nil {
+		return formatCompilerError(markdownPath, "error", err.Error(), err)
+	}
+
 	// Validate safe-outputs allowed-domains configuration
 	log.Printf("Validating safe-outputs allowed-domains")
 	if err := c.validateSafeOutputsAllowedDomains(workflowData.SafeOutputs); err != nil {
diff --git a/pkg/workflow/safe_outputs_max_validation_test.go b/pkg/workflow/safe_outputs_max_validation_test.go
new file mode 100644
index 00000000000..c99d24cd9c6
--- /dev/null
+++ b/pkg/workflow/safe_outputs_max_validation_test.go
@@ -0,0 +1,235 @@
+//go:build !integration
+
+package workflow
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+func TestValidateSafeOutputsMax(t *testing.T) {
+	t.Run("nil config is valid", func(t *testing.T) {
+		err := validateSafeOutputsMax(nil)
+		assert.NoError(t, err, "nil config should be valid")
+	})
+
+	t.Run("config with no max fields is valid", func(t *testing.T) {
+		config := &SafeOutputsConfig{}
+		err := validateSafeOutputsMax(config)
+		assert.NoError(t, err, "config with no max fields should be valid")
+	})
+
+	t.Run("max of 1 is valid", func(t *testing.T) {
+		config := &SafeOutputsConfig{
+			AddComments: &AddCommentsConfig{
+				BaseSafeOutputConfig: BaseSafeOutputConfig{Max: strPtr("1")},
+			},
+		}
+		err := validateSafeOutputsMax(config)
+		assert.NoError(t, err, "max: 1 should be valid")
+	})
+
+	t.Run("max of 5 is valid", func(t *testing.T) {
+		config := &SafeOutputsConfig{
+			CreateIssues: &CreateIssuesConfig{
+				BaseSafeOutputConfig: BaseSafeOutputConfig{Max: strPtr("5")},
+			},
+		}
+		err := validateSafeOutputsMax(config)
+		assert.NoError(t, err, "max: 5 should be valid")
+	})
+
+	t.Run("max of -1 is valid (unlimited)", func(t *testing.T) {
+		config := &SafeOutputsConfig{
+			AddComments: &AddCommentsConfig{
+				BaseSafeOutputConfig: BaseSafeOutputConfig{Max: strPtr("-1")},
+			},
+		}
+		err := validateSafeOutputsMax(config)
+		assert.NoError(t, err, "max: -1 should be valid (means unlimited per spec)")
+	})
+
+	t.Run("max of 0 is invalid", func(t *testing.T) {
+		config := &SafeOutputsConfig{
+			AddComments: &AddCommentsConfig{
+				BaseSafeOutputConfig: BaseSafeOutputConfig{Max: strPtr("0")},
+			},
+		}
+		err := validateSafeOutputsMax(config)
+		require.Error(t, err, "max: 0 should be invalid")
+		assert.Contains(t, err.Error(), "max must be a positive integer or -1", "error should explain valid values")
+		assert.Contains(t, err.Error(), "add-comment", "error should mention the field name")
+	})
+
+	t.Run("max of -2 is invalid", func(t *testing.T) {
+		config := &SafeOutputsConfig{
+			CreateIssues: &CreateIssuesConfig{
+				BaseSafeOutputConfig: BaseSafeOutputConfig{Max: strPtr("-2")},
+			},
+		}
+		err := validateSafeOutputsMax(config)
+		require.Error(t, err, "max: -2 should be invalid")
+		assert.Contains(t, err.Error(), "max must be a positive integer or -1", "error should explain valid values")
+	})
+
+	t.Run("max as GitHub Actions expression is skipped", func(t *testing.T) {
+		config := &SafeOutputsConfig{
+			AddComments: &AddCommentsConfig{
+				BaseSafeOutputConfig: BaseSafeOutputConfig{Max: strPtr("${{ inputs.max }}")},
+			},
+		}
+		err := validateSafeOutputsMax(config)
+		assert.NoError(t, err, "GitHub Actions expression should be skipped")
+	})
+
+	t.Run("nil max is valid", func(t *testing.T) {
+		config := &SafeOutputsConfig{
+			AddComments: &AddCommentsConfig{
+				BaseSafeOutputConfig: BaseSafeOutputConfig{Max: nil},
+			},
+		}
+		err := validateSafeOutputsMax(config)
+		assert.NoError(t, err, "nil max should be valid")
+	})
+
+	t.Run("dispatch_repository tool max of 0 is invalid", func(t *testing.T) {
+		maxVal := "0"
+		config := &SafeOutputsConfig{
+			DispatchRepository: &DispatchRepositoryConfig{
+				Tools: map[string]*DispatchRepositoryToolConfig{
+					"my-tool": {Max: &maxVal},
+				},
+			},
+		}
+		err := validateSafeOutputsMax(config)
+		require.Error(t, err, "dispatch_repository max: 0 should be invalid")
+		assert.Contains(t, err.Error(), "max must be a positive integer or -1", "error should explain valid values")
+		assert.Contains(t, err.Error(), "my-tool", "error should mention the tool name")
+		assert.Contains(t, err.Error(), "dispatch_repository", "error should use underscore form")
+	})
+
+	t.Run("dispatch_repository tool max of -1 is valid (unlimited)", func(t *testing.T) {
+		maxVal := "-1"
+		config := &SafeOutputsConfig{
+			DispatchRepository: &DispatchRepositoryConfig{
+				Tools: map[string]*DispatchRepositoryToolConfig{
+					"my-tool": {Max: &maxVal},
+				},
+			},
+		}
+		err := validateSafeOutputsMax(config)
+		assert.NoError(t, err, "dispatch_repository max: -1 should be valid")
+	})
+
+	t.Run("dispatch_repository tool max of 1 is valid", func(t *testing.T) {
+		maxVal := "1"
+		config := &SafeOutputsConfig{
+			DispatchRepository: &DispatchRepositoryConfig{
+				Tools: map[string]*DispatchRepositoryToolConfig{
+					"my-tool": {Max: &maxVal},
+				},
+			},
+		}
+		err := validateSafeOutputsMax(config)
+		assert.NoError(t, err, "dispatch_repository max: 1 should be valid")
+	})
+
+	t.Run("dispatch_repository tool max as expression is skipped", func(t *testing.T) {
+		maxVal := "${{ inputs.max }}"
+		config := &SafeOutputsConfig{
+			DispatchRepository: &DispatchRepositoryConfig{
+				Tools: map[string]*DispatchRepositoryToolConfig{
+					"my-tool": {Max: &maxVal},
+				},
+			},
+		}
+		err := validateSafeOutputsMax(config)
+		assert.NoError(t, err, "GitHub Actions expression for dispatch_repository should be skipped")
+	})
+
+	t.Run("multiple configs with one invalid returns error", func(t *testing.T) {
+		config := &SafeOutputsConfig{
+			AddComments: &AddCommentsConfig{
+				BaseSafeOutputConfig: BaseSafeOutputConfig{Max: strPtr("3")},
+			},
+			CreateIssues: &CreateIssuesConfig{
+				BaseSafeOutputConfig: BaseSafeOutputConfig{Max: strPtr("0")},
+			},
+		}
+		err := validateSafeOutputsMax(config)
+		require.Error(t, err, "config with one invalid max should return error")
+		assert.Contains(t, err.Error(), "max must be a positive integer or -1", "error should explain valid values")
+	})
+}
+
+func TestValidateSafeOutputsMaxIntegration(t *testing.T) {
+	compiler := &Compiler{}
+
+	t.Run("max of 0 is rejected during config extraction via compiler", func(t *testing.T) {
+		frontmatter := map[string]any{
+			"safe-outputs": map[string]any{
+				"add-comment": map[string]any{
+					"max": 0,
+				},
+			},
+		}
+
+		config := compiler.extractSafeOutputsConfig(frontmatter)
+		require.NotNil(t, config, "config should be extracted")
+
+		err := validateSafeOutputsMax(config)
+		require.Error(t, err, "max: 0 should fail validation")
+		assert.Contains(t, err.Error(), "max must be a positive integer or -1", "error message should explain valid values")
+	})
+
+	t.Run("max of -2 is rejected during config extraction via compiler", func(t *testing.T) {
+		frontmatter := map[string]any{
+			"safe-outputs": map[string]any{
+				"create-issue": map[string]any{
+					"max": -2,
+				},
+			},
+		}
+
+		config := compiler.extractSafeOutputsConfig(frontmatter)
+		require.NotNil(t, config, "config should be extracted")
+
+		err := validateSafeOutputsMax(config)
+		require.Error(t, err, "max: -2 should fail validation")
+		assert.Contains(t, err.Error(), "max must be a positive integer or -1", "error message should explain valid values")
+	})
+
+	t.Run("max of -1 passes validation (unlimited)", func(t *testing.T) {
+		frontmatter := map[string]any{
+			"safe-outputs": map[string]any{
+				"add-comment": map[string]any{
+					"max": -1,
+				},
+			},
+		}
+
+		config := compiler.extractSafeOutputsConfig(frontmatter)
+		require.NotNil(t, config, "config should be extracted")
+
+		err := validateSafeOutputsMax(config)
+		assert.NoError(t, err, "max: -1 should pass validation (unlimited per spec)")
+	})
+
+	t.Run("max of 1 passes validation", func(t *testing.T) {
+		frontmatter := map[string]any{
+			"safe-outputs": map[string]any{
+				"add-comment": map[string]any{
+					"max": 1,
+				},
+			},
+		}
+
+		config := compiler.extractSafeOutputsConfig(frontmatter)
+		require.NotNil(t, config, "config should be extracted")
+
+		err := validateSafeOutputsMax(config)
+		assert.NoError(t, err, "max: 1 should pass validation")
+	})
+}
diff --git a/pkg/workflow/safe_outputs_validation.go b/pkg/workflow/safe_outputs_validation.go
index cb466de0650..1cefdfebae9 100644
--- a/pkg/workflow/safe_outputs_validation.go
+++ b/pkg/workflow/safe_outputs_validation.go
@@ -2,7 +2,10 @@ package workflow
 
 import (
 	"fmt"
+	"reflect"
 	"regexp"
+	"sort"
+	"strconv"
 	"strings"
 
 	"github.com/github/gh-aw/pkg/stringutil"
@@ -405,3 +408,112 @@ func isGitHubExpression(s string) bool {
 	// and there must be something between them
 	return openIndex >= 0 && closeIndex > openIndex+3
 }
+
+var safeOutputsMaxValidationLog = newValidationLogger("safe_outputs_max")
+
+// isInvalidMaxValue returns true if n is not a valid max field value.
+// Valid values are positive integers (n > 0) or -1 (unlimited).
+// Invalid values are 0 and negative integers except -1.
+func isInvalidMaxValue(n int) bool {
+	if n == -1 {
+		return false // -1 = unlimited, explicitly allowed by spec
+	}
+	return n <= 0
+}
+
+// maxInvalidErrSuffix is the common suffix of max validation error messages.
+const maxInvalidErrSuffix = "\n\nThe max field controls how many times this safe output can be triggered.\nProvide a positive integer (e.g., max: 1 or max: 5) or -1 for unlimited"
+
+// validateSafeOutputsMax validates that all max fields in safe-outputs configs hold valid values.
+// Valid values are positive integers (n > 0) or -1 (unlimited per spec).
+// 0 and other negative values are rejected.
+// GitHub Actions expressions (e.g. "${{ inputs.max }}") are not evaluable at compile time
+// and are therefore skipped.
+func validateSafeOutputsMax(config *SafeOutputsConfig) error {
+	if config == nil {
+		return nil
+	}
+
+	safeOutputsMaxValidationLog.Print("Validating safe-outputs max fields")
+
+	val := reflect.ValueOf(config).Elem()
+
+	// Iterate over sorted field names for deterministic error reporting.
+	sortedFieldNames := make([]string, 0, len(safeOutputFieldMapping))
+	for fieldName := range safeOutputFieldMapping {
+		sortedFieldNames = append(sortedFieldNames, fieldName)
+	}
+	sort.Strings(sortedFieldNames)
+
+	// Validate max on all named safe output fields that embed BaseSafeOutputConfig
+	for _, fieldName := range sortedFieldNames {
+		toolName := safeOutputFieldMapping[fieldName]
+		field := val.FieldByName(fieldName)
+		if !field.IsValid() || field.IsNil() {
+			continue
+		}
+
+		elem := field.Elem()
+		baseCfgField := elem.FieldByName("BaseSafeOutputConfig")
+		if !baseCfgField.IsValid() {
+			continue
+		}
+
+		maxField := baseCfgField.FieldByName("Max")
+		if !maxField.IsValid() || maxField.IsNil() {
+			continue
+		}
+
+		maxPtr, ok := maxField.Interface().(*string)
+		if !ok || maxPtr == nil || isExpressionString(*maxPtr) {
+			continue
+		}
+
+		n, err := strconv.Atoi(*maxPtr)
+		if err != nil {
+			continue
+		}
+
+		if isInvalidMaxValue(n) {
+			toolDisplayName := strings.ReplaceAll(toolName, "_", "-")
+			safeOutputsMaxValidationLog.Printf("Invalid max value %d for %s", n, toolDisplayName)
+			return fmt.Errorf(
+				"safe-outputs.%s: max must be a positive integer or -1 (unlimited), got %d%s",
+				toolDisplayName, n, maxInvalidErrSuffix,
+			)
+		}
+	}
+
+	// Validate max on dispatch_repository tools (different structure: map of tools).
+	// Use sorted tool names for deterministic error reporting.
+	if config.DispatchRepository != nil {
+		sortedToolNames := make([]string, 0, len(config.DispatchRepository.Tools))
+		for toolName := range config.DispatchRepository.Tools {
+			sortedToolNames = append(sortedToolNames, toolName)
+		}
+		sort.Strings(sortedToolNames)
+
+		for _, toolName := range sortedToolNames {
+			tool := config.DispatchRepository.Tools[toolName]
+			if tool == nil || tool.Max == nil || isExpressionString(*tool.Max) {
+				continue
+			}
+
+			n, err := strconv.Atoi(*tool.Max)
+			if err != nil {
+				continue
+			}
+
+			if isInvalidMaxValue(n) {
+				safeOutputsMaxValidationLog.Printf("Invalid max value %d for dispatch_repository tool %s", n, toolName)
+				return fmt.Errorf(
+					"safe-outputs.dispatch_repository.%s: max must be a positive integer or -1 (unlimited), got %d%s",
+					toolName, n, maxInvalidErrSuffix,
+				)
+			}
+		}
+	}
+
+	safeOutputsMaxValidationLog.Print("Safe-outputs max fields validation passed")
+	return nil
+}