diff --git a/.github/workflows/mcp-inspector.lock.yml b/.github/workflows/mcp-inspector.lock.yml
index cdeeddf93e9..a651357db6d 100644
--- a/.github/workflows/mcp-inspector.lock.yml
+++ b/.github/workflows/mcp-inspector.lock.yml
@@ -674,7 +674,7 @@ jobs:
         env:
           GH_AW_FILE_ROOT: "${{ runner.temp }}/gh-aw"
           GH_AW_FILE_CONFIG: "{\"files\":[{\"path\":\"safeoutputs/config.json\",\"content_env\":\"GH_AW_SAFE_OUTPUTS_CONFIG\"}]}"
-          GH_AW_SAFE_OUTPUTS_CONFIG: "{\"create_discussion\":{\"category\":\"audits\",\"close_older_discussions\":true,\"expires\":24,\"fallback_to_issue\":true,\"max\":1,\"title_prefix\":\"[mcp-inspector] \"},\"create_report_incomplete_issue\":{},\"missing_data\":{},\"missing_tool\":{},\"noop\":{\"max\":1,\"report-as-issue\":\"false\"},\"post-to-slack-channel\":{\"description\":\"Post a message to a Slack channel. Message must be 200 characters or less. Supports basic Slack markdown: *bold*, _italic_, ~strike~, `code`, ```code block```, \\u003equote, and links \\u003curl|text\\u003e. Requires GH_AW_SLACK_CHANNEL_ID environment variable to be set.\",\"inputs\":{\"message\":{\"default\":null,\"description\":\"The message to post (max 200 characters, supports Slack markdown)\",\"required\":true,\"type\":\"string\"}},\"output\":\"Message posted to Slack successfully!\"},\"report_incomplete\":{}}"
+          GH_AW_SAFE_OUTPUTS_CONFIG: "{\"create_discussion\":{\"category\":\"audits\",\"close_older_discussions\":true,\"expires\":24,\"fallback_to_issue\":true,\"max\":1,\"title_prefix\":\"[mcp-inspector] \"},\"create_report_incomplete_issue\":{},\"missing_data\":{},\"missing_tool\":{},\"noop\":{\"max\":1,\"report-as-issue\":\"false\"},\"post-to-slack-channel\":{\"description\":\"Post a message to a Slack channel. Message must be 200 characters or less. Supports basic Slack markdown: *bold*, _italic_, ~strike~, `code`, ```code block```, >quote, and links <url|text>. Requires GH_AW_SLACK_CHANNEL_ID environment variable to be set.\",\"inputs\":{\"message\":{\"default\":null,\"description\":\"The message to post (max 200 characters, supports Slack markdown)\",\"required\":true,\"type\":\"string\"}},\"output\":\"Message posted to Slack successfully!\"},\"report_incomplete\":{}}"
         with:
           script: |
             const path = require('path');
diff --git a/pkg/workflow/compiler_safe_outputs_builder.go b/pkg/workflow/compiler_safe_outputs_builder.go
index 4d72e9e28a0..9f1ce1df701 100644
--- a/pkg/workflow/compiler_safe_outputs_builder.go
+++ b/pkg/workflow/compiler_safe_outputs_builder.go
@@ -9,6 +9,7 @@ import (
 	"strings"
 	"sync/atomic"
 
+	"github.com/github/gh-aw/pkg/jsonutil"
 	"github.com/github/gh-aw/pkg/logger"
 )
 
@@ -150,18 +151,19 @@ func (b *handlerConfigBuilder) AddTemplatableJSONSlice(key string, value []strin
 }
 
 func marshalSafeOutputsConfig(config map[string]any) ([]byte, error) {
-	configJSON, err := json.Marshal(config)
+	configJSON, err := jsonutil.MarshalCompactNoHTMLEscape(config)
 	if err != nil {
 		return nil, err
 	}
+	result := []byte(configJSON)
 	for _, expression := range templatableJSONExpressions(config) {
-		placeholder, err := json.Marshal(expression.placeholder())
+		placeholderJSON, err := jsonutil.MarshalCompactNoHTMLEscape(expression.placeholder())
 		if err != nil {
 			return nil, err
 		}
-		configJSON = bytes.ReplaceAll(configJSON, placeholder, []byte(expression.expr))
+		result = bytes.ReplaceAll(result, []byte(placeholderJSON), []byte(expression.expr))
 	}
-	return configJSON, nil
+	return result, nil
 }
 
 var (
diff --git a/pkg/workflow/compiler_safe_outputs_config_targets_test.go b/pkg/workflow/compiler_safe_outputs_config_targets_test.go
index d09bb6190f6..4db1345a9a6 100644
--- a/pkg/workflow/compiler_safe_outputs_config_targets_test.go
+++ b/pkg/workflow/compiler_safe_outputs_config_targets_test.go
@@ -120,6 +120,29 @@ func TestHandlerConfigClosePullRequestTargetRepo(t *testing.T) {
 	}
 }
 
+func TestMarshalSafeOutputsConfigPreservesExpressionOperators(t *testing.T) {
+	configJSON, err := marshalSafeOutputsConfig(map[string]any{
+		"create_issue": map[string]any{
+			"target-repo": "${{ condition && value || fallback }}",
+		},
+	})
+
+	require.NoError(t, err)
+	assert.Contains(t, string(configJSON), "${{ condition && value || fallback }}")
+	assert.NotContains(t, string(configJSON), `\u0026`)
+}
+
+func TestMarshalSafeOutputsConfigPreservesTemplatableExpressionOperators(t *testing.T) {
+	builder := newHandlerConfigBuilder()
+	builder.AddTemplatableJSONSlice("items", []string{"${{ condition && value || fallback }}"})
+
+	configJSON, err := marshalSafeOutputsConfig(builder.config)
+
+	require.NoError(t, err)
+	assert.Contains(t, string(configJSON), "${{ toJSON(condition && value || fallback) }}")
+	assert.NotContains(t, string(configJSON), `\u0026`)
+}
+
 func TestHandlerConfigCreateCheckRunTarget(t *testing.T) {
 	compiler := NewCompiler()