diff --git a/apps/server/src/api-data/automation/__tests__/automation.service.test.ts b/apps/server/src/api-data/automation/__tests__/automation.service.test.ts
index 817f3d7df..031cf2a8c 100644
--- a/apps/server/src/api-data/automation/__tests__/automation.service.test.ts
+++ b/apps/server/src/api-data/automation/__tests__/automation.service.test.ts
@@ -112,6 +112,26 @@ describe('testConditions()', () => {
       const result = testConditions([{ field: 'eventNow.title', operator: 'equals', value: '' }], 'all', mockStore);
       expect(result).toBe(true);
     });
+
+    it('should handle trueness boolean comparisons', () => {
+      const mockStore = makeRuntimeStateData({ eventNow: { countToEnd: true } as PlayableEvent });
+      expect(
+        testConditions([{ field: 'eventNow.countToEnd', operator: 'equals', value: 'true' }], 'all', mockStore),
+      ).toBe(true);
+      expect(
+        testConditions([{ field: 'eventNow.countToEnd', operator: 'equals', value: 'false' }], 'all', mockStore),
+      ).toBe(false);
+    });
+
+    it('should handle falseness boolean comparisons', () => {
+      const mockStore = makeRuntimeStateData({ eventNow: { countToEnd: false } as PlayableEvent });
+      expect(
+        testConditions([{ field: 'eventNow.countToEnd', operator: 'equals', value: 'false' }], 'all', mockStore),
+      ).toBe(true);
+      expect(
+        testConditions([{ field: 'eventNow.countToEnd', operator: 'equals', value: 'true' }], 'all', mockStore),
+      ).toBe(false);
+    });
   });
 
   describe('not_equals operator', () => {
diff --git a/apps/server/src/api-data/automation/automation.service.ts b/apps/server/src/api-data/automation/automation.service.ts
index 1aa6ab349..c5fbffec2 100644
--- a/apps/server/src/api-data/automation/automation.service.ts
+++ b/apps/server/src/api-data/automation/automation.service.ts
@@ -14,7 +14,7 @@ import { isOntimeCloud } from '../../externals.js';
 import { emitOSC } from './clients/osc.client.js';
 import { emitHTTP } from './clients/http.client.js';
 import { getAutomationsEnabled, getAutomations, getAutomationTriggers } from './automation.dao.js';
-import { isGreaterThan, isLessThan } from './automation.utils.js';
+import { isBooleanEquals, isGreaterThan, isLessThan } from './automation.utils.js';
 
 /**
  * Exposes a method for triggering actions based on a TimerLifeCycle event
@@ -74,12 +74,18 @@ export function testConditions(
 
   function evaluateCondition(filter: AutomationFilter): boolean {
     const { field, operator, value } = filter;
+    const lowerCasedValue = value.toLowerCase();
     const fieldValue = getPropertyFromPath(field, state);
 
     // if value is empty string, the user could be meaning to check if the value does not exist
     // we use loose equality to be able to check for converted values (eg '10' == 10)
     switch (operator) {
       case 'equals':
+        // handle the case where we are comparing boolean strings
+
+        if (typeof fieldValue === 'boolean') {
+          return isBooleanEquals(fieldValue, lowerCasedValue);
+        }
         // overload the edge case where we use empty string to check if a value does not exist
         if (value === '' && fieldValue === undefined) {
           return true;
@@ -88,14 +94,8 @@ export function testConditions(
       case 'not_equals':
         return fieldValue != value;
       case 'greater_than':
-        if (typeof fieldValue !== 'number') {
-          return false;
-        }
         return isGreaterThan(fieldValue, value);
       case 'less_than':
-        if (typeof fieldValue !== 'number') {
-          return false;
-        }
         return isLessThan(fieldValue, value);
       case 'contains':
         return typeof fieldValue === 'string' && fieldValue.includes(value);
diff --git a/apps/server/src/api-data/automation/automation.utils.ts b/apps/server/src/api-data/automation/automation.utils.ts
index 72eb0539d..b3929d584 100644
--- a/apps/server/src/api-data/automation/automation.utils.ts
+++ b/apps/server/src/api-data/automation/automation.utils.ts
@@ -79,7 +79,8 @@ export function parseTemplateNested(template: string, state: object, humanReadab
         value = undefined;
       }
     } else {
-      value = getPropertyFromPath(variableName, state);
+      // we cast to string since this will be used in a string context
+      value = getPropertyFromPath(variableName, state) as string;
     }
     if (value !== undefined) {
       parsedTemplate = parsedTemplate.replace(match[0], value);
@@ -140,17 +141,18 @@ const quickAliases: AliasesDefinition = {
  * @example isGreaterThan('5', '10') // false
  * @example isGreaterThan('Ontime', 'Cool') // false
  */
-export function isGreaterThan(a: string, b: string): boolean {
-  const aValue = Number(a);
-  const bValue = Number(b);
-
-  // we check if the values encore numbers and compare them
-  if (!isNaN(aValue) && !isNaN(bValue)) {
-    return aValue > bValue;
+export function isGreaterThan(a: unknown, b: string): boolean {
+  // If either value is not a number, there is no logical comparison to be made
+  if (typeof a !== 'number') {
+    return false;
   }
 
-  // If either value is not a number, there is no logical comparison to be made
-  return false;
+  const bValue = Number(b);
+  if (isNaN(bValue)) {
+    return false;
+  }
+
+  return a > bValue;
 }
 
 /**
@@ -159,15 +161,33 @@ export function isGreaterThan(a: string, b: string): boolean {
  * @example isLessThan('5', '10') // true
  * @example isLessThan('Ontime', 'Cool') // false
  */
-export function isLessThan(a: string, b: string): boolean {
-  const aValue = Number(a);
-  const bValue = Number(b);
-
-  // we check if the values encore numbers and compare them
-  if (!isNaN(aValue) && !isNaN(bValue)) {
-    return aValue < bValue;
+export function isLessThan(a: unknown, b: string): boolean {
+  // If either value is not a number, there is no logical comparison to be made
+  if (typeof a !== 'number') {
+    return false;
   }
 
-  // If either value is not a number, there is no logical comparison to be made
+  const bValue = Number(b);
+  if (isNaN(bValue)) {
+    return false;
+  }
+
+  return a < bValue;
+}
+
+/**
+ * Utility encapsulates logic for comparing two strings which may encode booleans
+ * @example isBooleanEquals(true, 'true') // true
+ * @example isBooleanEquals(true, 'false') // false
+ * @example isBooleanEquals(true, 'something') // false
+ */
+export function isBooleanEquals(a: boolean, b: string): boolean {
+  if (b === 'true') {
+    return a === true;
+  }
+
+  if (b === 'false') {
+    return a === false;
+  }
   return false;
 }