diff --git a/db/knex_migrations/2024-08-24-0000-conditions.js b/db/knex_migrations/2024-08-24-0000-conditions.js
new file mode 100644
index 000000000..96352fdc4
--- /dev/null
+++ b/db/knex_migrations/2024-08-24-0000-conditions.js
@@ -0,0 +1,12 @@
+exports.up = function (knex) {
+    return knex.schema
+        .alterTable("monitor", function (table) {
+            table.text("conditions").notNullable().defaultTo("[]");
+        });
+};
+
+exports.down = function (knex) {
+    return knex.schema.alterTable("monitor", function (table) {
+        table.dropColumn("conditions");
+    });
+};
diff --git a/server/client.js b/server/client.js
index 58ed8f956..72f0a4e8e 100644
--- a/server/client.js
+++ b/server/client.js
@@ -213,6 +213,32 @@ async function sendRemoteBrowserList(socket) {
     return list;
 }
 
+/**
+ * Send list of monitor types to client
+ * @param {Socket} socket Socket.io socket instance
+ * @returns {Promise<void>}
+ */
+async function sendMonitorTypeList(socket) {
+    const result = Object.entries(UptimeKumaServer.monitorTypeList).map(([ key, type ]) => {
+        return [ key, {
+            supportsConditions: type.supportsConditions,
+            conditionVariables: type.conditionVariables.map(v => {
+                return {
+                    id: v.id,
+                    operators: v.operators.map(o => {
+                        return {
+                            id: o.id,
+                            caption: o.caption,
+                        };
+                    }),
+                };
+            }),
+        }];
+    });
+
+    io.to(socket.userID).emit("monitorTypeList", Object.fromEntries(result));
+}
+
 module.exports = {
     sendNotificationList,
     sendImportantHeartbeatList,
@@ -222,4 +248,5 @@ module.exports = {
     sendInfo,
     sendDockerHostList,
     sendRemoteBrowserList,
+    sendMonitorTypeList,
 };
diff --git a/server/model/monitor.js b/server/model/monitor.js
index 73901e807..b55e98918 100644
--- a/server/model/monitor.js
+++ b/server/model/monitor.js
@@ -164,6 +164,7 @@ class Monitor extends BeanModel {
             snmpOid: this.snmpOid,
             jsonPathOperator: this.jsonPathOperator,
             snmpVersion: this.snmpVersion,
+            conditions: JSON.parse(this.conditions),
         };
 
         if (includeSensitiveData) {
diff --git a/server/monitor-conditions/evaluator.js b/server/monitor-conditions/evaluator.js
new file mode 100644
index 000000000..3860a3325
--- /dev/null
+++ b/server/monitor-conditions/evaluator.js
@@ -0,0 +1,71 @@
+const { ConditionExpressionGroup, ConditionExpression, LOGICAL } = require("./expression");
+const { operatorMap } = require("./operators");
+
+/**
+ * @param {ConditionExpression} expression Expression to evaluate
+ * @param {object} context Context to evaluate against; These are values for variables in the expression
+ * @returns {boolean} Whether the expression evaluates true or false
+ * @throws {Error}
+ */
+function evaluateExpression(expression, context) {
+    /**
+     * @type {import("./operators").ConditionOperator|null}
+     */
+    const operator = operatorMap.get(expression.operator) || null;
+    if (operator === null) {
+        throw new Error("Unexpected expression operator ID '" + expression.operator + "'. Expected one of [" + operatorMap.keys().join(",") + "]");
+    }
+
+    if (!Object.prototype.hasOwnProperty.call(context, expression.variable)) {
+        throw new Error("Variable missing in context: " + expression.variable);
+    }
+
+    return operator.test(context[expression.variable], expression.value);
+}
+
+/**
+ * @param {ConditionExpressionGroup} group Group of expressions to evaluate
+ * @param {object} context Context to evaluate against; These are values for variables in the expression
+ * @returns {boolean} Whether the group evaluates true or false
+ * @throws {Error}
+ */
+function evaluateExpressionGroup(group, context) {
+    if (!group.children.length) {
+        throw new Error("ConditionExpressionGroup must contain at least one child.");
+    }
+
+    let result = null;
+
+    for (const child of group.children) {
+        let childResult;
+
+        if (child instanceof ConditionExpression) {
+            childResult = evaluateExpression(child, context);
+        } else if (child instanceof ConditionExpressionGroup) {
+            childResult = evaluateExpressionGroup(child, context);
+        } else {
+            throw new Error("Invalid child type in ConditionExpressionGroup. Expected ConditionExpression or ConditionExpressionGroup");
+        }
+
+        if (result === null) {
+            result = childResult; // Initialize result with the first child's result
+        } else if (child.andOr === LOGICAL.OR) {
+            result = result || childResult;
+        } else if (child.andOr === LOGICAL.AND) {
+            result = result && childResult;
+        } else {
+            throw new Error("Invalid logical operator in child of ConditionExpressionGroup. Expected 'and' or 'or'. Got '" + group.andOr + "'");
+        }
+    }
+
+    if (result === null) {
+        throw new Error("ConditionExpressionGroup did not result in a boolean.");
+    }
+
+    return result;
+}
+
+module.exports = {
+    evaluateExpression,
+    evaluateExpressionGroup,
+};
diff --git a/server/monitor-conditions/expression.js b/server/monitor-conditions/expression.js
new file mode 100644
index 000000000..1e7036959
--- /dev/null
+++ b/server/monitor-conditions/expression.js
@@ -0,0 +1,111 @@
+/**
+ * @readonly
+ * @enum {string}
+ */
+const LOGICAL = {
+    AND: "and",
+    OR: "or",
+};
+
+/**
+ * Recursively processes an array of raw condition objects and populates the given parent group with
+ * corresponding ConditionExpression or ConditionExpressionGroup instances.
+ * @param {Array} conditions Array of raw condition objects, where each object represents either a group or an expression.
+ * @param {ConditionExpressionGroup} parentGroup The parent group to which the instantiated ConditionExpression or ConditionExpressionGroup objects will be added.
+ * @returns {void}
+ */
+function processMonitorConditions(conditions, parentGroup) {
+    conditions.forEach(condition => {
+        const andOr = condition.andOr === LOGICAL.OR ? LOGICAL.OR : LOGICAL.AND;
+
+        if (condition.type === "group") {
+            const group = new ConditionExpressionGroup([], andOr);
+
+            // Recursively process the group's children
+            processMonitorConditions(condition.children, group);
+
+            parentGroup.children.push(group);
+        } else if (condition.type === "expression") {
+            const expression = new ConditionExpression(condition.variable, condition.operator, condition.value, andOr);
+            parentGroup.children.push(expression);
+        }
+    });
+}
+
+class ConditionExpressionGroup {
+    /**
+     * @type {ConditionExpressionGroup[]|ConditionExpression[]} Groups and/or expressions to test
+     */
+    children = [];
+
+    /**
+     * @type {LOGICAL} Connects group result with previous group/expression results
+     */
+    andOr;
+
+    /**
+     * @param {ConditionExpressionGroup[]|ConditionExpression[]} children Groups and/or expressions to test
+     * @param {LOGICAL} andOr Connects group result with previous group/expression results
+     */
+    constructor(children = [], andOr = LOGICAL.AND) {
+        this.children = children;
+        this.andOr = andOr;
+    }
+
+    /**
+     * @param {Monitor} monitor Monitor instance
+     * @returns {ConditionExpressionGroup|null} A ConditionExpressionGroup with the Monitor's conditions
+     */
+    static fromMonitor(monitor) {
+        const conditions = JSON.parse(monitor.conditions);
+        if (conditions.length === 0) {
+            return null;
+        }
+
+        const root = new ConditionExpressionGroup();
+        processMonitorConditions(conditions, root);
+
+        return root;
+    }
+}
+
+class ConditionExpression {
+    /**
+     * @type {string} ID of variable
+     */
+    variable;
+
+    /**
+     * @type {string} ID of operator
+     */
+    operator;
+
+    /**
+     * @type {string} Value to test with the operator
+     */
+    value;
+
+    /**
+     * @type {LOGICAL} Connects expression result with previous group/expression results
+     */
+    andOr;
+
+    /**
+     * @param {string} variable ID of variable to test against
+     * @param {string} operator ID of operator to test the variable with
+     * @param {string} value Value to test with the operator
+     * @param {LOGICAL} andOr Connects expression result with previous group/expression results
+     */
+    constructor(variable, operator, value, andOr = LOGICAL.AND) {
+        this.variable = variable;
+        this.operator = operator;
+        this.value = value;
+        this.andOr = andOr;
+    }
+}
+
+module.exports = {
+    LOGICAL,
+    ConditionExpressionGroup,
+    ConditionExpression,
+};
diff --git a/server/monitor-conditions/operators.js b/server/monitor-conditions/operators.js
new file mode 100644
index 000000000..d900dff9d
--- /dev/null
+++ b/server/monitor-conditions/operators.js
@@ -0,0 +1,318 @@
+class ConditionOperator {
+    id = undefined;
+    caption = undefined;
+
+    /**
+     * @type {mixed} variable
+     * @type {mixed} value
+     */
+    test(variable, value) {
+        throw new Error("You need to override test()");
+    }
+}
+
+const OP_STR_EQUALS = "equals";
+
+const OP_STR_NOT_EQUALS = "not_equals";
+
+const OP_CONTAINS = "contains";
+
+const OP_NOT_CONTAINS = "not_contains";
+
+const OP_STARTS_WITH = "starts_with";
+
+const OP_NOT_STARTS_WITH = "not_starts_with";
+
+const OP_ENDS_WITH = "ends_with";
+
+const OP_NOT_ENDS_WITH = "not_ends_with";
+
+const OP_NUM_EQUALS = "num_equals";
+
+const OP_NUM_NOT_EQUALS = "num_not_equals";
+
+const OP_LT = "lt";
+
+const OP_GT = "gt";
+
+const OP_LTE = "lte";
+
+const OP_GTE = "gte";
+
+/**
+ * Asserts a variable is equal to a value.
+ */
+class StringEqualsOperator extends ConditionOperator {
+    id = OP_STR_EQUALS;
+    caption = "equals";
+
+    /**
+     * @inheritdoc
+     */
+    test(variable, value) {
+        return variable === value;
+    }
+}
+
+/**
+ * Asserts a variable is not equal to a value.
+ */
+class StringNotEqualsOperator extends ConditionOperator {
+    id = OP_STR_NOT_EQUALS;
+    caption = "not equals";
+
+    /**
+     * @inheritdoc
+     */
+    test(variable, value) {
+        return variable !== value;
+    }
+}
+
+/**
+ * Asserts a variable contains a value.
+ * Handles both Array and String variable types.
+ */
+class ContainsOperator extends ConditionOperator {
+    id = OP_CONTAINS;
+    caption = "contains";
+
+    /**
+     * @inheritdoc
+     */
+    test(variable, value) {
+        if (Array.isArray(variable)) {
+            return variable.includes(value);
+        }
+
+        return variable.indexOf(value) !== -1;
+    }
+}
+
+/**
+ * Asserts a variable does not contain a value.
+ * Handles both Array and String variable types.
+ */
+class NotContainsOperator extends ConditionOperator {
+    id = OP_NOT_CONTAINS;
+    caption = "not contains";
+
+    /**
+     * @inheritdoc
+     */
+    test(variable, value) {
+        if (Array.isArray(variable)) {
+            return !variable.includes(value);
+        }
+
+        return variable.indexOf(value) === -1;
+    }
+}
+
+/**
+ * Asserts a variable starts with a value.
+ */
+class StartsWithOperator extends ConditionOperator {
+    id = OP_STARTS_WITH;
+    caption = "starts with";
+
+    /**
+     * @inheritdoc
+     */
+    test(variable, value) {
+        return variable.startsWith(value);
+    }
+}
+
+/**
+ * Asserts a variable does not start with a value.
+ */
+class NotStartsWithOperator extends ConditionOperator {
+    id = OP_NOT_STARTS_WITH;
+    caption = "not starts with";
+
+    /**
+     * @inheritdoc
+     */
+    test(variable, value) {
+        return !variable.startsWith(value);
+    }
+}
+
+/**
+ * Asserts a variable ends with a value.
+ */
+class EndsWithOperator extends ConditionOperator {
+    id = OP_ENDS_WITH;
+    caption = "ends with";
+
+    /**
+     * @inheritdoc
+     */
+    test(variable, value) {
+        return variable.endsWith(value);
+    }
+}
+
+/**
+ * Asserts a variable does not end with a value.
+ */
+class NotEndsWithOperator extends ConditionOperator {
+    id = OP_NOT_ENDS_WITH;
+    caption = "not ends with";
+
+    /**
+     * @inheritdoc
+     */
+    test(variable, value) {
+        return !variable.endsWith(value);
+    }
+}
+
+/**
+ * Asserts a numeric variable is equal to a value.
+ */
+class NumberEqualsOperator extends ConditionOperator {
+    id = OP_NUM_EQUALS;
+    caption = "equals";
+
+    /**
+     * @inheritdoc
+     */
+    test(variable, value) {
+        return variable === Number(value);
+    }
+}
+
+/**
+ * Asserts a numeric variable is not equal to a value.
+ */
+class NumberNotEqualsOperator extends ConditionOperator {
+    id = OP_NUM_NOT_EQUALS;
+    caption = "not equals";
+
+    /**
+     * @inheritdoc
+     */
+    test(variable, value) {
+        return variable !== Number(value);
+    }
+}
+
+/**
+ * Asserts a variable is less than a value.
+ */
+class LessThanOperator extends ConditionOperator {
+    id = OP_LT;
+    caption = "less than";
+
+    /**
+     * @inheritdoc
+     */
+    test(variable, value) {
+        return variable < Number(value);
+    }
+}
+
+/**
+ * Asserts a variable is greater than a value.
+ */
+class GreaterThanOperator extends ConditionOperator {
+    id = OP_GT;
+    caption = "greater than";
+
+    /**
+     * @inheritdoc
+     */
+    test(variable, value) {
+        return variable > Number(value);
+    }
+}
+
+/**
+ * Asserts a variable is less than or equal to a value.
+ */
+class LessThanOrEqualToOperator extends ConditionOperator {
+    id = OP_LTE;
+    caption = "less than or equal to";
+
+    /**
+     * @inheritdoc
+     */
+    test(variable, value) {
+        return variable <= Number(value);
+    }
+}
+
+/**
+ * Asserts a variable is greater than or equal to a value.
+ */
+class GreaterThanOrEqualToOperator extends ConditionOperator {
+    id = OP_GTE;
+    caption = "greater than or equal to";
+
+    /**
+     * @inheritdoc
+     */
+    test(variable, value) {
+        return variable >= Number(value);
+    }
+}
+
+const operatorMap = new Map([
+    [ OP_STR_EQUALS, new StringEqualsOperator ],
+    [ OP_STR_NOT_EQUALS, new StringNotEqualsOperator ],
+    [ OP_CONTAINS, new ContainsOperator ],
+    [ OP_NOT_CONTAINS, new NotContainsOperator ],
+    [ OP_STARTS_WITH, new StartsWithOperator ],
+    [ OP_NOT_STARTS_WITH, new NotStartsWithOperator ],
+    [ OP_ENDS_WITH, new EndsWithOperator ],
+    [ OP_NOT_ENDS_WITH, new NotEndsWithOperator ],
+    [ OP_NUM_EQUALS, new NumberEqualsOperator ],
+    [ OP_NUM_NOT_EQUALS, new NumberNotEqualsOperator ],
+    [ OP_LT, new LessThanOperator ],
+    [ OP_GT, new GreaterThanOperator ],
+    [ OP_LTE, new LessThanOrEqualToOperator ],
+    [ OP_GTE, new GreaterThanOrEqualToOperator ],
+]);
+
+const defaultStringOperators = [
+    operatorMap.get(OP_STR_EQUALS),
+    operatorMap.get(OP_STR_NOT_EQUALS),
+    operatorMap.get(OP_CONTAINS),
+    operatorMap.get(OP_NOT_CONTAINS),
+    operatorMap.get(OP_STARTS_WITH),
+    operatorMap.get(OP_NOT_STARTS_WITH),
+    operatorMap.get(OP_ENDS_WITH),
+    operatorMap.get(OP_NOT_ENDS_WITH)
+];
+
+const defaultNumberOperators = [
+    operatorMap.get(OP_NUM_EQUALS),
+    operatorMap.get(OP_NUM_NOT_EQUALS),
+    operatorMap.get(OP_LT),
+    operatorMap.get(OP_GT),
+    operatorMap.get(OP_LTE),
+    operatorMap.get(OP_GTE)
+];
+
+module.exports = {
+    OP_STR_EQUALS,
+    OP_STR_NOT_EQUALS,
+    OP_CONTAINS,
+    OP_NOT_CONTAINS,
+    OP_STARTS_WITH,
+    OP_NOT_STARTS_WITH,
+    OP_ENDS_WITH,
+    OP_NOT_ENDS_WITH,
+    OP_NUM_EQUALS,
+    OP_NUM_NOT_EQUALS,
+    OP_LT,
+    OP_GT,
+    OP_LTE,
+    OP_GTE,
+    operatorMap,
+    defaultStringOperators,
+    defaultNumberOperators,
+    ConditionOperator,
+};
diff --git a/server/monitor-conditions/variables.js b/server/monitor-conditions/variables.js
new file mode 100644
index 000000000..af98d2f29
--- /dev/null
+++ b/server/monitor-conditions/variables.js
@@ -0,0 +1,31 @@
+/**
+ * Represents a variable used in a condition and the set of operators that can be applied to this variable.
+ *
+ * A `ConditionVariable` holds the ID of the variable and a list of operators that define how this variable can be evaluated
+ * in conditions. For example, if the variable is a request body or a specific field in a request, the operators can include
+ * operations such as equality checks, comparisons, or other custom evaluations.
+ */
+class ConditionVariable {
+    /**
+     * @type {string}
+     */
+    id;
+
+    /**
+     * @type {import("./operators").ConditionOperator[]}
+     */
+    operators = {};
+
+    /**
+     * @param {string} id ID of variable
+     * @param {import("./operators").ConditionOperator[]} operators Operators the condition supports
+     */
+    constructor(id, operators = []) {
+        this.id = id;
+        this.operators = operators;
+    }
+}
+
+module.exports = {
+    ConditionVariable,
+};
diff --git a/server/monitor-types/dns.js b/server/monitor-types/dns.js
index d038b6805..8b87932fe 100644
--- a/server/monitor-types/dns.js
+++ b/server/monitor-types/dns.js
@@ -1,12 +1,22 @@
 const { MonitorType } = require("./monitor-type");
-const { UP } = require("../../src/util");
+const { UP, DOWN } = require("../../src/util");
 const dayjs = require("dayjs");
 const { dnsResolve } = require("../util-server");
 const { R } = require("redbean-node");
+const { ConditionVariable } = require("../monitor-conditions/variables");
+const { defaultStringOperators } = require("../monitor-conditions/operators");
+const { ConditionExpressionGroup } = require("../monitor-conditions/expression");
+const { evaluateExpressionGroup } = require("../monitor-conditions/evaluator");
 
 class DnsMonitorType extends MonitorType {
     name = "dns";
 
+    supportsConditions = true;
+
+    conditionVariables = [
+        new ConditionVariable("record", defaultStringOperators ),
+    ];
+
     /**
      * @inheritdoc
      */
@@ -17,28 +27,48 @@ class DnsMonitorType extends MonitorType {
         let dnsRes = await dnsResolve(monitor.hostname, monitor.dns_resolve_server, monitor.port, monitor.dns_resolve_type);
         heartbeat.ping = dayjs().valueOf() - startTime;
 
-        if (monitor.dns_resolve_type === "A" || monitor.dns_resolve_type === "AAAA" || monitor.dns_resolve_type === "TXT" || monitor.dns_resolve_type === "PTR") {
-            dnsMessage += "Records: ";
-            dnsMessage += dnsRes.join(" | ");
-        } else if (monitor.dns_resolve_type === "CNAME" || monitor.dns_resolve_type === "PTR") {
-            dnsMessage += dnsRes[0];
-        } else if (monitor.dns_resolve_type === "CAA") {
-            dnsMessage += dnsRes[0].issue;
-        } else if (monitor.dns_resolve_type === "MX") {
-            dnsRes.forEach(record => {
-                dnsMessage += `Hostname: ${record.exchange} - Priority: ${record.priority} | `;
-            });
-            dnsMessage = dnsMessage.slice(0, -2);
-        } else if (monitor.dns_resolve_type === "NS") {
-            dnsMessage += "Servers: ";
-            dnsMessage += dnsRes.join(" | ");
-        } else if (monitor.dns_resolve_type === "SOA") {
-            dnsMessage += `NS-Name: ${dnsRes.nsname} | Hostmaster: ${dnsRes.hostmaster} | Serial: ${dnsRes.serial} | Refresh: ${dnsRes.refresh} | Retry: ${dnsRes.retry} | Expire: ${dnsRes.expire} | MinTTL: ${dnsRes.minttl}`;
-        } else if (monitor.dns_resolve_type === "SRV") {
-            dnsRes.forEach(record => {
-                dnsMessage += `Name: ${record.name} | Port: ${record.port} | Priority: ${record.priority} | Weight: ${record.weight} | `;
-            });
-            dnsMessage = dnsMessage.slice(0, -2);
+        const conditions = ConditionExpressionGroup.fromMonitor(monitor);
+        let conditionsResult = true;
+        const handleConditions = (data) => conditions ? evaluateExpressionGroup(conditions, data) : true;
+
+        switch (monitor.dns_resolve_type) {
+            case "A":
+            case "AAAA":
+            case "TXT":
+            case "PTR":
+                dnsMessage = `Records: ${dnsRes.join(" | ")}`;
+                conditionsResult = dnsRes.some(record => handleConditions({ record }));
+                break;
+
+            case "CNAME":
+                dnsMessage = dnsRes[0];
+                conditionsResult = handleConditions({ record: dnsRes[0] });
+                break;
+
+            case "CAA":
+                dnsMessage = dnsRes[0].issue;
+                conditionsResult = handleConditions({ record: dnsRes[0].issue });
+                break;
+
+            case "MX":
+                dnsMessage = dnsRes.map(record => `Hostname: ${record.exchange} - Priority: ${record.priority}`).join(" | ");
+                conditionsResult = dnsRes.some(record => handleConditions({ record: record.exchange }));
+                break;
+
+            case "NS":
+                dnsMessage = `Servers: ${dnsRes.join(" | ")}`;
+                conditionsResult = dnsRes.some(record => handleConditions({ record }));
+                break;
+
+            case "SOA":
+                dnsMessage = `NS-Name: ${dnsRes.nsname} | Hostmaster: ${dnsRes.hostmaster} | Serial: ${dnsRes.serial} | Refresh: ${dnsRes.refresh} | Retry: ${dnsRes.retry} | Expire: ${dnsRes.expire} | MinTTL: ${dnsRes.minttl}`;
+                conditionsResult = handleConditions({ record: dnsRes.nsname });
+                break;
+
+            case "SRV":
+                dnsMessage = dnsRes.map(record => `Name: ${record.name} | Port: ${record.port} | Priority: ${record.priority} | Weight: ${record.weight}`).join(" | ");
+                conditionsResult = dnsRes.some(record => handleConditions({ record: record.name }));
+                break;
         }
 
         if (monitor.dns_last_result !== dnsMessage && dnsMessage !== undefined) {
@@ -46,7 +76,7 @@ class DnsMonitorType extends MonitorType {
         }
 
         heartbeat.msg = dnsMessage;
-        heartbeat.status = UP;
+        heartbeat.status = conditionsResult ? UP : DOWN;
     }
 }
 
diff --git a/server/monitor-types/monitor-type.js b/server/monitor-types/monitor-type.js
index 8290bdd76..8f3cbcac4 100644
--- a/server/monitor-types/monitor-type.js
+++ b/server/monitor-types/monitor-type.js
@@ -1,6 +1,19 @@
 class MonitorType {
     name = undefined;
 
+    /**
+     * Whether or not this type supports monitor conditions. Controls UI visibility in monitor form.
+     * @type {boolean}
+     */
+    supportsConditions = false;
+
+    /**
+     * Variables supported by this type. e.g. an HTTP type could have a "response_code" variable to test against.
+     * This property controls the choices displayed in the monitor edit form.
+     * @type {import("../monitor-conditions/variables").ConditionVariable[]}
+     */
+    conditionVariables = [];
+
     /**
      * Run the monitoring check on the given monitor
      * @param {Monitor} monitor Monitor to check
diff --git a/server/server.js b/server/server.js
index 21491da9a..1f27b3c43 100644
--- a/server/server.js
+++ b/server/server.js
@@ -132,7 +132,7 @@ const twoFAVerifyOptions = {
 const testMode = !!args["test"] || false;
 
 // Must be after io instantiation
-const { sendNotificationList, sendHeartbeatList, sendInfo, sendProxyList, sendDockerHostList, sendAPIKeyList, sendRemoteBrowserList } = require("./client");
+const { sendNotificationList, sendHeartbeatList, sendInfo, sendProxyList, sendDockerHostList, sendAPIKeyList, sendRemoteBrowserList, sendMonitorTypeList } = require("./client");
 const { statusPageSocketHandler } = require("./socket-handlers/status-page-socket-handler");
 const { databaseSocketHandler } = require("./socket-handlers/database-socket-handler");
 const { remoteBrowserSocketHandler } = require("./socket-handlers/remote-browser-socket-handler");
@@ -716,6 +716,8 @@ let needSetup = false;
                 monitor.kafkaProducerBrokers = JSON.stringify(monitor.kafkaProducerBrokers);
                 monitor.kafkaProducerSaslOptions = JSON.stringify(monitor.kafkaProducerSaslOptions);
 
+                monitor.conditions = JSON.stringify(monitor.conditions);
+
                 bean.import(monitor);
                 bean.user_id = socket.userID;
 
@@ -866,6 +868,7 @@ let needSetup = false;
                 bean.snmpOid = monitor.snmpOid;
                 bean.jsonPathOperator = monitor.jsonPathOperator;
                 bean.timeout = monitor.timeout;
+                bean.conditions = JSON.stringify(monitor.conditions);
 
                 bean.validate();
 
@@ -1671,6 +1674,7 @@ async function afterLogin(socket, user) {
         sendDockerHostList(socket),
         sendAPIKeyList(socket),
         sendRemoteBrowserList(socket),
+        sendMonitorTypeList(socket),
     ]);
 
     await StatusPage.sendStatusPageList(io, socket);
diff --git a/src/components/EditMonitorCondition.vue b/src/components/EditMonitorCondition.vue
new file mode 100644
index 000000000..ac1b02dd2
--- /dev/null
+++ b/src/components/EditMonitorCondition.vue
@@ -0,0 +1,152 @@
+<template>
+    <div class="monitor-condition mb-3" data-testid="condition">
+        <button
+            v-if="!isInGroup || !isFirst || !isLast"
+            class="btn btn-outline-danger remove-button"
+            type="button"
+            :aria-label="$t('conditionDelete')"
+            data-testid="remove-condition"
+            @click="remove"
+        >
+            <font-awesome-icon icon="trash" />
+        </button>
+
+        <select v-if="!isFirst" v-model="model.andOr" class="form-select and-or-select" data-testid="condition-and-or">
+            <option value="and">{{ $t("and") }}</option>
+            <option value="or">{{ $t("or") }}</option>
+        </select>
+
+        <select v-model="model.variable" class="form-select" data-testid="condition-variable">
+            <option
+                v-for="variable in conditionVariables"
+                :key="variable.id"
+                :value="variable.id"
+            >
+                {{ $t(variable.id) }}
+            </option>
+        </select>
+
+        <select v-model="model.operator" class="form-select" data-testid="condition-operator">
+            <option
+                v-for="operator in getVariableOperators(model.variable)"
+                :key="operator.id"
+                :value="operator.id"
+            >
+                {{ $t(operator.caption) }}
+            </option>
+        </select>
+
+        <input
+            v-model="model.value"
+            type="text"
+            class="form-control"
+            :aria-label="$t('conditionValuePlaceholder')"
+            data-testid="condition-value"
+            required
+        />
+    </div>
+</template>
+
+<script>
+export default {
+    name: "EditMonitorCondition",
+
+    props: {
+        /**
+         * The monitor condition
+         */
+        modelValue: {
+            type: Object,
+            required: true,
+        },
+
+        /**
+         * Whether this is the first condition
+         */
+        isFirst: {
+            type: Boolean,
+            required: true,
+        },
+
+        /**
+         * Whether this is the last condition
+         */
+        isLast: {
+            type: Boolean,
+            required: true,
+        },
+
+        /**
+         * Whether this condition is in a group
+         */
+        isInGroup: {
+            type: Boolean,
+            required: false,
+            default: false,
+        },
+
+        /**
+         * Variable choices
+         */
+        conditionVariables: {
+            type: Array,
+            required: true,
+        },
+    },
+
+    emits: [ "update:modelValue", "remove" ],
+
+    computed: {
+        model: {
+            get() {
+                return this.modelValue;
+            },
+            set(value) {
+                this.$emit("update:modelValue", value);
+            }
+        }
+    },
+
+    methods: {
+        remove() {
+            this.$emit("remove", this.model);
+        },
+
+        getVariableOperators(variableId) {
+            return this.conditionVariables.find(v => v.id === variableId)?.operators ?? [];
+        },
+    },
+};
+</script>
+
+<style lang="scss" scoped>
+@import "../assets/vars.scss";
+
+.monitor-condition {
+    display: flex;
+    flex-wrap: wrap;
+}
+
+.remove-button {
+    justify-self: flex-end;
+    margin-bottom: 12px;
+    margin-left: auto;
+}
+
+@container (min-width: 500px) {
+    .monitor-condition {
+        display: flex;
+        flex-wrap: nowrap;
+    }
+
+    .remove-button {
+        margin-bottom: 0;
+        margin-left: 10px;
+        order: 100;
+    }
+
+    .and-or-select {
+        width: auto;
+    }
+}
+</style>
diff --git a/src/components/EditMonitorConditionGroup.vue b/src/components/EditMonitorConditionGroup.vue
new file mode 100644
index 000000000..910b41508
--- /dev/null
+++ b/src/components/EditMonitorConditionGroup.vue
@@ -0,0 +1,189 @@
+<template>
+    <div class="condition-group mb-3" data-testid="condition-group">
+        <div class="d-flex">
+            <select v-if="!isFirst" v-model="model.andOr" class="form-select" style="width: auto;" data-testid="condition-group-and-or">
+                <option value="and">{{ $t("and") }}</option>
+                <option value="or">{{ $t("or") }}</option>
+            </select>
+        </div>
+
+        <div class="condition-group-inner mt-2 pa-2">
+            <div class="condition-group-conditions">
+                <template v-for="(child, childIndex) in model.children" :key="childIndex">
+                    <EditMonitorConditionGroup
+                        v-if="child.type === 'group'"
+                        v-model="model.children[childIndex]"
+                        :is-first="childIndex === 0"
+                        :get-new-group="getNewGroup"
+                        :get-new-condition="getNewCondition"
+                        :condition-variables="conditionVariables"
+                        @remove="removeChild"
+                    />
+                    <EditMonitorCondition
+                        v-else
+                        v-model="model.children[childIndex]"
+                        :is-first="childIndex === 0"
+                        :is-last="childIndex === model.children.length - 1"
+                        :is-in-group="true"
+                        :condition-variables="conditionVariables"
+                        @remove="removeChild"
+                    />
+                </template>
+            </div>
+
+            <div class="condition-group-actions mt-3">
+                <button class="btn btn-outline-secondary me-2" type="button" data-testid="add-condition-button" @click="addCondition">
+                    {{ $t("conditionAdd") }}
+                </button>
+                <button class="btn btn-outline-secondary me-2" type="button" data-testid="add-group-button" @click="addGroup">
+                    {{ $t("conditionAddGroup") }}
+                </button>
+                <button
+                    class="btn btn-outline-danger"
+                    type="button"
+                    :aria-label="$t('conditionDeleteGroup')"
+                    data-testid="remove-condition-group"
+                    @click="remove"
+                >
+                    <font-awesome-icon icon="trash" />
+                </button>
+            </div>
+        </div>
+    </div>
+</template>
+
+<script>
+import EditMonitorCondition from "./EditMonitorCondition.vue";
+
+export default {
+    name: "EditMonitorConditionGroup",
+
+    components: {
+        EditMonitorCondition,
+    },
+
+    props: {
+        /**
+         * The condition group
+         */
+        modelValue: {
+            type: Object,
+            required: true,
+        },
+
+        /**
+         * Whether this is the first condition
+         */
+        isFirst: {
+            type: Boolean,
+            required: true,
+        },
+
+        /**
+         * Function to generate a new group model
+         */
+        getNewGroup: {
+            type: Function,
+            required: true,
+        },
+
+        /**
+         * Function to generate a new condition model
+         */
+        getNewCondition: {
+            type: Function,
+            required: true,
+        },
+
+        /**
+         * Variable choices
+         */
+        conditionVariables: {
+            type: Array,
+            required: true,
+        },
+    },
+
+    emits: [ "update:modelValue", "remove" ],
+
+    computed: {
+        model: {
+            get() {
+                return this.modelValue;
+            },
+            set(value) {
+                this.$emit("update:modelValue", value);
+            }
+        }
+    },
+
+    methods: {
+        addGroup() {
+            const conditions = [ ...this.model.children ];
+            conditions.push(this.getNewGroup());
+            this.model.children = conditions;
+        },
+
+        addCondition() {
+            const conditions = [ ...this.model.children ];
+            conditions.push(this.getNewCondition());
+            this.model.children = conditions;
+        },
+
+        remove() {
+            this.$emit("remove", this.model);
+        },
+
+        removeChild(child) {
+            const idx = this.model.children.indexOf(child);
+            if (idx !== -1) {
+                this.model.children.splice(idx, 1);
+            }
+        },
+    },
+};
+</script>
+
+<style lang="scss" scoped>
+@import "../assets/vars.scss";
+
+.condition-group-inner {
+    background: rgba(0, 0, 0, 0.05);
+    padding: 20px;
+}
+
+.dark .condition-group-inner {
+    background: rgba(255, 255, 255, 0.05);
+}
+
+.condition-group-conditions {
+    container-type: inline-size;
+}
+
+.condition-group-actions {
+    display: grid;
+    gap: 10px;
+}
+
+// Delete button
+.condition-group-actions > :last-child {
+    margin-left: auto;
+    margin-top: 14px;
+}
+
+@container (min-width: 400px) {
+    .condition-group-actions {
+        display: flex;
+    }
+
+    // Delete button
+    .condition-group-actions > :last-child {
+        margin-left: auto;
+        margin-top: 0;
+    }
+
+    .btn-delete-group {
+        margin-left: auto;
+    }
+}
+</style>
diff --git a/src/components/EditMonitorConditions.vue b/src/components/EditMonitorConditions.vue
new file mode 100644
index 000000000..60f7c6589
--- /dev/null
+++ b/src/components/EditMonitorConditions.vue
@@ -0,0 +1,149 @@
+<template>
+    <div class="monitor-conditions">
+        <label class="form-label">{{ $t("Conditions") }}</label>
+        <div class="monitor-conditions-conditions">
+            <template v-for="(condition, conditionIndex) in model" :key="conditionIndex">
+                <EditMonitorConditionGroup
+                    v-if="condition.type === 'group'"
+                    v-model="model[conditionIndex]"
+                    :is-first="conditionIndex === 0"
+                    :get-new-group="getNewGroup"
+                    :get-new-condition="getNewCondition"
+                    :condition-variables="conditionVariables"
+                    @remove="removeCondition"
+                />
+                <EditMonitorCondition
+                    v-else
+                    v-model="model[conditionIndex]"
+                    :is-first="conditionIndex === 0"
+                    :is-last="conditionIndex === model.length - 1"
+                    :condition-variables="conditionVariables"
+                    @remove="removeCondition"
+                />
+            </template>
+        </div>
+        <div class="monitor-conditions-buttons">
+            <button class="btn btn-outline-secondary me-2" type="button" data-testid="add-condition-button" @click="addCondition">
+                {{ $t("conditionAdd") }}
+            </button>
+            <button class="btn btn-outline-secondary me-2" type="button" data-testid="add-group-button" @click="addGroup">
+                {{ $t("conditionAddGroup") }}
+            </button>
+        </div>
+    </div>
+</template>
+
+<script>
+import EditMonitorConditionGroup from "./EditMonitorConditionGroup.vue";
+import EditMonitorCondition from "./EditMonitorCondition.vue";
+
+export default {
+    name: "EditMonitorConditions",
+
+    components: {
+        EditMonitorConditionGroup,
+        EditMonitorCondition,
+    },
+
+    props: {
+        /**
+         * The monitor conditions
+         */
+        modelValue: {
+            type: Array,
+            required: true,
+        },
+
+        conditionVariables: {
+            type: Array,
+            required: true,
+        },
+    },
+
+    emits: [ "update:modelValue" ],
+
+    computed: {
+        model: {
+            get() {
+                return this.modelValue;
+            },
+            set(value) {
+                this.$emit("update:modelValue", value);
+            }
+        }
+    },
+
+    created() {
+        if (this.model.length === 0) {
+            this.addCondition();
+        }
+    },
+
+    methods: {
+        getNewGroup() {
+            return {
+                type: "group",
+                children: [ this.getNewCondition() ],
+                andOr: "and",
+            };
+        },
+
+        getNewCondition() {
+            const firstVariable = this.conditionVariables[0]?.id || null;
+            const firstOperator = this.getVariableOperators(firstVariable)[0] || null;
+            return {
+                type: "expression",
+                variable: firstVariable,
+                operator: firstOperator?.id || null,
+                value: "",
+                andOr: "and",
+            };
+        },
+
+        addGroup() {
+            const conditions = [ ...this.model ];
+            conditions.push(this.getNewGroup());
+            this.$emit("update:modelValue", conditions);
+        },
+
+        addCondition() {
+            const conditions = [ ...this.model ];
+            conditions.push(this.getNewCondition());
+            this.$emit("update:modelValue", conditions);
+        },
+
+        removeCondition(condition) {
+            const conditions = [ ...this.model ];
+            const idx = conditions.indexOf(condition);
+            if (idx !== -1) {
+                conditions.splice(idx, 1);
+                this.$emit("update:modelValue", conditions);
+            }
+        },
+
+        getVariableOperators(variableId) {
+            return this.conditionVariables.find(v => v.id === variableId)?.operators ?? [];
+        },
+    },
+};
+</script>
+
+<style lang="scss" scoped>
+@import "../assets/vars.scss";
+
+.monitor-conditions,
+.monitor-conditions-conditions {
+    container-type: inline-size;
+}
+
+.monitor-conditions-buttons {
+    display: grid;
+    gap: 10px;
+}
+
+@container (min-width: 400px) {
+    .monitor-conditions-buttons {
+        display: flex;
+    }
+}
+</style>
diff --git a/src/lang/en.json b/src/lang/en.json
index a09f01627..e8b74a9e8 100644
--- a/src/lang/en.json
+++ b/src/lang/en.json
@@ -444,6 +444,7 @@
     "backupOutdatedWarning": "Deprecated: Since a lot of features were added and this backup feature is a bit unmaintained, it cannot generate or restore a complete backup.",
     "backupRecommend": "Please backup the volume or the data folder (./data/) directly instead.",
     "Optional": "Optional",
+    "and": "and",
     "or": "or",
     "sameAsServerTimezone": "Same as Server Timezone",
     "startDateTime": "Start Date/Time",
@@ -994,5 +995,24 @@
     "Cannot connect to the socket server.": "Cannot connect to the socket server.",
     "SIGNL4": "SIGNL4",
     "SIGNL4 Webhook URL": "SIGNL4 Webhook URL",
-    "signl4Docs": "You can find more information about how to configure SIGNL4 and how to obtain the SIGNL4 webhook URL in the {0}."
+    "signl4Docs": "You can find more information about how to configure SIGNL4 and how to obtain the SIGNL4 webhook URL in the {0}.",
+    "Conditions": "Conditions",
+    "conditionAdd": "Add Condition",
+    "conditionDelete": "Delete Condition",
+    "conditionAddGroup": "Add Group",
+    "conditionDeleteGroup": "Delete Group",
+    "conditionValuePlaceholder": "Value",
+    "equals": "equals",
+    "not equals": "not equals",
+    "contains": "contains",
+    "not contains": "not contains",
+    "starts with": "starts with",
+    "not starts with": "not starts with",
+    "ends with": "ends with",
+    "not ends with": "not ends with",
+    "less than": "less than",
+    "greater than": "greater than",
+    "less than or equal to": "less than or equal to",
+    "greater than or equal to": "greater than or equal to",
+    "record": "record"
 }
diff --git a/src/mixins/socket.js b/src/mixins/socket.js
index f305cc7c1..4541161c2 100644
--- a/src/mixins/socket.js
+++ b/src/mixins/socket.js
@@ -38,6 +38,7 @@ export default {
             allowLoginDialog: false,        // Allowed to show login dialog, but "loggedIn" have to be true too. This exists because prevent the login dialog show 0.1s in first before the socket server auth-ed.
             loggedIn: false,
             monitorList: { },
+            monitorTypeList: {},
             maintenanceList: {},
             apiKeyList: {},
             heartbeatList: { },
@@ -153,6 +154,10 @@ export default {
                 this.monitorList = data;
             });
 
+            socket.on("monitorTypeList", (data) => {
+                this.monitorTypeList = data;
+            });
+
             socket.on("maintenanceList", (data) => {
                 this.maintenanceList = data;
             });
diff --git a/src/pages/Details.vue b/src/pages/Details.vue
index 16e45dab5..17d32365c 100644
--- a/src/pages/Details.vue
+++ b/src/pages/Details.vue
@@ -79,7 +79,7 @@
                         <span class="word">{{ $t("checkEverySecond", [ monitor.interval ]) }}</span>
                     </div>
                     <div class="col-md-4 text-center">
-                        <span class="badge rounded-pill" :class=" 'bg-' + status.color " style="font-size: 30px;">{{ status.text }}</span>
+                        <span class="badge rounded-pill" :class=" 'bg-' + status.color " style="font-size: 30px;" data-testid="monitor-status">{{ status.text }}</span>
                     </div>
                 </div>
             </div>
diff --git a/src/pages/EditMonitor.vue b/src/pages/EditMonitor.vue
index 8318bb7aa..eca386e0e 100644
--- a/src/pages/EditMonitor.vue
+++ b/src/pages/EditMonitor.vue
@@ -10,7 +10,7 @@
 
                             <div class="my-3">
                                 <label for="type" class="form-label">{{ $t("Monitor Type") }}</label>
-                                <select id="type" v-model="monitor.type" class="form-select">
+                                <select id="type" v-model="monitor.type" class="form-select" data-testid="monitor-type-select">
                                     <optgroup :label="$t('General Monitor Type')">
                                         <option value="group">
                                             {{ $t("Group") }}
@@ -99,7 +99,7 @@
                             <!-- Friendly Name -->
                             <div class="my-3">
                                 <label for="name" class="form-label">{{ $t("Friendly Name") }}</label>
-                                <input id="name" v-model="monitor.name" type="text" class="form-control" required>
+                                <input id="name" v-model="monitor.name" type="text" class="form-control" required data-testid="friendly-name-input">
                             </div>
 
                             <!-- URL -->
@@ -237,7 +237,15 @@
                             <!-- TCP Port / Ping / DNS / Steam / MQTT / Radius / Tailscale Ping / SNMP only -->
                             <div v-if="monitor.type === 'port' || monitor.type === 'ping' || monitor.type === 'dns' || monitor.type === 'steam' || monitor.type === 'gamedig' || monitor.type === 'mqtt' || monitor.type === 'radius' || monitor.type === 'tailscale-ping' || monitor.type === 'snmp'" class="my-3">
                                 <label for="hostname" class="form-label">{{ $t("Hostname") }}</label>
-                                <input id="hostname" v-model="monitor.hostname" type="text" class="form-control" :pattern="`${monitor.type === 'mqtt' ? mqttIpOrHostnameRegexPattern : ipOrHostnameRegexPattern}`" required>
+                                <input
+                                    id="hostname"
+                                    v-model="monitor.hostname"
+                                    type="text"
+                                    class="form-control"
+                                    :pattern="`${monitor.type === 'mqtt' ? mqttIpOrHostnameRegexPattern : ipOrHostnameRegexPattern}`"
+                                    required
+                                    data-testid="hostname-input"
+                                >
                             </div>
 
                             <!-- Port -->
@@ -343,6 +351,7 @@
                                         :preselect-first="false"
                                         :max-height="500"
                                         :taggable="false"
+                                        data-testid="resolve-type-select"
                                     ></VueMultiselect>
 
                                     <div class="form-text">
@@ -509,6 +518,14 @@
                                 </div>
                             </template>
 
+                            <!-- Conditions -->
+                            <EditMonitorConditions
+                                v-if="supportsConditions && conditionVariables.length > 0"
+                                v-model="monitor.conditions"
+                                :condition-variables="conditionVariables"
+                                class="my-3"
+                            />
+
                             <!-- Interval -->
                             <div class="my-3">
                                 <label for="interval" class="form-label">{{ $t("Heartbeat Interval") }} ({{ $t("checkEverySecond", [ monitor.interval ]) }})</label>
@@ -963,7 +980,15 @@
                     </div>
 
                     <div class="fixed-bottom-bar p-3">
-                        <button id="monitor-submit-btn" class="btn btn-primary" type="submit" :disabled="processing">{{ $t("Save") }}</button>
+                        <button
+                            id="monitor-submit-btn"
+                            class="btn btn-primary"
+                            type="submit"
+                            :disabled="processing"
+                            data-testid="save-button"
+                        >
+                            {{ $t("Save") }}
+                        </button>
                     </div>
                 </div>
             </form>
@@ -972,7 +997,7 @@
             <DockerHostDialog ref="dockerHostDialog" @added="addedDockerHost" />
             <ProxyDialog ref="proxyDialog" @added="addedProxy" />
             <CreateGroupDialog ref="createGroupDialog" @added="addedDraftGroup" />
-            <RemoteBrowserDialog ref="remoteBrowserDialog" @added="addedRemoteBrowser" />
+            <RemoteBrowserDialog ref="remoteBrowserDialog" />
         </div>
     </transition>
 </template>
@@ -991,6 +1016,7 @@ import TagsManager from "../components/TagsManager.vue";
 import { genSecret, isDev, MAX_INTERVAL_SECOND, MIN_INTERVAL_SECOND, sleep } from "../util.ts";
 import { hostNameRegexPattern } from "../util-frontend";
 import HiddenInput from "../components/HiddenInput.vue";
+import EditMonitorConditions from "../components/EditMonitorConditions.vue";
 
 const toast = useToast;
 
@@ -1034,7 +1060,8 @@ const monitorDefaults = {
     kafkaProducerSsl: false,
     kafkaProducerAllowAutoTopicCreation: false,
     gamedigGivenPortOnly: true,
-    remote_browser: null
+    remote_browser: null,
+    conditions: []
 };
 
 export default {
@@ -1049,6 +1076,7 @@ export default {
         RemoteBrowserDialog,
         TagsManager,
         VueMultiselect,
+        EditMonitorConditions,
     },
 
     data() {
@@ -1303,7 +1331,15 @@ message HealthCheckResponse {
                     value: null,
                 }];
             }
-        }
+        },
+
+        supportsConditions() {
+            return this.$root.monitorTypeList[this.monitor.type]?.supportsConditions || false;
+        },
+
+        conditionVariables() {
+            return this.$root.monitorTypeList[this.monitor.type]?.conditionVariables || [];
+        },
     },
     watch: {
         "$root.proxyList"() {
@@ -1336,7 +1372,7 @@ message HealthCheckResponse {
             }
         },
 
-        "monitor.type"() {
+        "monitor.type"(newType, oldType) {
             if (this.monitor.type === "push") {
                 if (! this.monitor.pushToken) {
                     // ideally this would require checking if the generated token is already used
@@ -1408,6 +1444,10 @@ message HealthCheckResponse {
                 }
             }
 
+            // Reset conditions since condition variables likely change:
+            if (oldType && newType !== oldType) {
+                this.monitor.conditions = [];
+            }
         },
 
         currentGameObject(newGameObject, previousGameObject) {
diff --git a/test/backend-test/monitor-conditions/test-evaluator.js b/test/backend-test/monitor-conditions/test-evaluator.js
new file mode 100644
index 000000000..da7c7fabf
--- /dev/null
+++ b/test/backend-test/monitor-conditions/test-evaluator.js
@@ -0,0 +1,46 @@
+const test = require("node:test");
+const assert = require("node:assert");
+const { ConditionExpressionGroup, ConditionExpression, LOGICAL } = require("../../../server/monitor-conditions/expression.js");
+const { evaluateExpressionGroup, evaluateExpression } = require("../../../server/monitor-conditions/evaluator.js");
+
+test("Test evaluateExpression", async (t) => {
+    const expr = new ConditionExpression("record", "contains", "mx1.example.com");
+    assert.strictEqual(true, evaluateExpression(expr, { record: "mx1.example.com" }));
+    assert.strictEqual(false, evaluateExpression(expr, { record: "mx2.example.com" }));
+});
+
+test("Test evaluateExpressionGroup with logical AND", async (t) => {
+    const group = new ConditionExpressionGroup([
+        new ConditionExpression("record", "contains", "mx1."),
+        new ConditionExpression("record", "contains", "example.com", LOGICAL.AND),
+    ]);
+    assert.strictEqual(true, evaluateExpressionGroup(group, { record: "mx1.example.com" }));
+    assert.strictEqual(false, evaluateExpressionGroup(group, { record: "mx1." }));
+    assert.strictEqual(false, evaluateExpressionGroup(group, { record: "example.com" }));
+});
+
+test("Test evaluateExpressionGroup with logical OR", async (t) => {
+    const group = new ConditionExpressionGroup([
+        new ConditionExpression("record", "contains", "example.com"),
+        new ConditionExpression("record", "contains", "example.org", LOGICAL.OR),
+    ]);
+    assert.strictEqual(true, evaluateExpressionGroup(group, { record: "example.com" }));
+    assert.strictEqual(true, evaluateExpressionGroup(group, { record: "example.org" }));
+    assert.strictEqual(false, evaluateExpressionGroup(group, { record: "example.net" }));
+});
+
+test("Test evaluateExpressionGroup with nested group", async (t) => {
+    const group = new ConditionExpressionGroup([
+        new ConditionExpression("record", "contains", "mx1."),
+        new ConditionExpressionGroup([
+            new ConditionExpression("record", "contains", "example.com"),
+            new ConditionExpression("record", "contains", "example.org", LOGICAL.OR),
+        ]),
+    ]);
+    assert.strictEqual(false, evaluateExpressionGroup(group, { record: "mx1." }));
+    assert.strictEqual(true, evaluateExpressionGroup(group, { record: "mx1.example.com" }));
+    assert.strictEqual(true, evaluateExpressionGroup(group, { record: "mx1.example.org" }));
+    assert.strictEqual(false, evaluateExpressionGroup(group, { record: "example.com" }));
+    assert.strictEqual(false, evaluateExpressionGroup(group, { record: "example.org" }));
+    assert.strictEqual(false, evaluateExpressionGroup(group, { record: "mx1.example.net" }));
+});
diff --git a/test/backend-test/monitor-conditions/test-expressions.js b/test/backend-test/monitor-conditions/test-expressions.js
new file mode 100644
index 000000000..fc723a244
--- /dev/null
+++ b/test/backend-test/monitor-conditions/test-expressions.js
@@ -0,0 +1,55 @@
+const test = require("node:test");
+const assert = require("node:assert");
+const { ConditionExpressionGroup, ConditionExpression } = require("../../../server/monitor-conditions/expression.js");
+
+test("Test ConditionExpressionGroup.fromMonitor", async (t) => {
+    const monitor = {
+        conditions: JSON.stringify([
+            {
+                "type": "expression",
+                "andOr": "and",
+                "operator": "contains",
+                "value": "foo",
+                "variable": "record"
+            },
+            {
+                "type": "group",
+                "andOr": "and",
+                "children": [
+                    {
+                        "type": "expression",
+                        "andOr": "and",
+                        "operator": "contains",
+                        "value": "bar",
+                        "variable": "record"
+                    },
+                    {
+                        "type": "group",
+                        "andOr": "and",
+                        "children": [
+                            {
+                                "type": "expression",
+                                "andOr": "and",
+                                "operator": "contains",
+                                "value": "car",
+                                "variable": "record"
+                            }
+                        ]
+                    },
+                ]
+            },
+        ]),
+    };
+    const root = ConditionExpressionGroup.fromMonitor(monitor);
+    assert.strictEqual(true, root.children.length === 2);
+    assert.strictEqual(true, root.children[0] instanceof ConditionExpression);
+    assert.strictEqual(true, root.children[0].value === "foo");
+    assert.strictEqual(true, root.children[1] instanceof ConditionExpressionGroup);
+    assert.strictEqual(true, root.children[1].children.length === 2);
+    assert.strictEqual(true, root.children[1].children[0] instanceof ConditionExpression);
+    assert.strictEqual(true, root.children[1].children[0].value === "bar");
+    assert.strictEqual(true, root.children[1].children[1] instanceof ConditionExpressionGroup);
+    assert.strictEqual(true, root.children[1].children[1].children.length === 1);
+    assert.strictEqual(true, root.children[1].children[1].children[0] instanceof ConditionExpression);
+    assert.strictEqual(true, root.children[1].children[1].children[0].value === "car");
+});
diff --git a/test/backend-test/monitor-conditions/test-operators.js b/test/backend-test/monitor-conditions/test-operators.js
new file mode 100644
index 000000000..e663c9a50
--- /dev/null
+++ b/test/backend-test/monitor-conditions/test-operators.js
@@ -0,0 +1,108 @@
+const test = require("node:test");
+const assert = require("node:assert");
+const { operatorMap, OP_CONTAINS, OP_NOT_CONTAINS, OP_LT, OP_GT, OP_LTE, OP_GTE, OP_STR_EQUALS, OP_STR_NOT_EQUALS, OP_NUM_EQUALS, OP_NUM_NOT_EQUALS, OP_STARTS_WITH, OP_ENDS_WITH, OP_NOT_STARTS_WITH, OP_NOT_ENDS_WITH } = require("../../../server/monitor-conditions/operators.js");
+
+test("Test StringEqualsOperator", async (t) => {
+    const op = operatorMap.get(OP_STR_EQUALS);
+    assert.strictEqual(true, op.test("mx1.example.com", "mx1.example.com"));
+    assert.strictEqual(false, op.test("mx1.example.com", "mx1.example.org"));
+    assert.strictEqual(false, op.test("1", 1)); // strict equality
+});
+
+test("Test StringNotEqualsOperator", async (t) => {
+    const op = operatorMap.get(OP_STR_NOT_EQUALS);
+    assert.strictEqual(true, op.test("mx1.example.com", "mx1.example.org"));
+    assert.strictEqual(false, op.test("mx1.example.com", "mx1.example.com"));
+    assert.strictEqual(true, op.test(1, "1")); // variable is not typecasted (strict equality)
+});
+
+test("Test ContainsOperator with scalar", async (t) => {
+    const op = operatorMap.get(OP_CONTAINS);
+    assert.strictEqual(true, op.test("mx1.example.org", "example.org"));
+    assert.strictEqual(false, op.test("mx1.example.org", "example.com"));
+});
+
+test("Test ContainsOperator with array", async (t) => {
+    const op = operatorMap.get(OP_CONTAINS);
+    assert.strictEqual(true, op.test([ "example.org" ], "example.org"));
+    assert.strictEqual(false, op.test([ "example.org" ], "example.com"));
+});
+
+test("Test NotContainsOperator with scalar", async (t) => {
+    const op = operatorMap.get(OP_NOT_CONTAINS);
+    assert.strictEqual(true, op.test("example.org", ".com"));
+    assert.strictEqual(false, op.test("example.org", ".org"));
+});
+
+test("Test NotContainsOperator with array", async (t) => {
+    const op = operatorMap.get(OP_NOT_CONTAINS);
+    assert.strictEqual(true, op.test([ "example.org" ], "example.com"));
+    assert.strictEqual(false, op.test([ "example.org" ], "example.org"));
+});
+
+test("Test StartsWithOperator", async (t) => {
+    const op = operatorMap.get(OP_STARTS_WITH);
+    assert.strictEqual(true, op.test("mx1.example.com", "mx1"));
+    assert.strictEqual(false, op.test("mx1.example.com", "mx2"));
+});
+
+test("Test NotStartsWithOperator", async (t) => {
+    const op = operatorMap.get(OP_NOT_STARTS_WITH);
+    assert.strictEqual(true, op.test("mx1.example.com", "mx2"));
+    assert.strictEqual(false, op.test("mx1.example.com", "mx1"));
+});
+
+test("Test EndsWithOperator", async (t) => {
+    const op = operatorMap.get(OP_ENDS_WITH);
+    assert.strictEqual(true, op.test("mx1.example.com", "example.com"));
+    assert.strictEqual(false, op.test("mx1.example.com", "example.net"));
+});
+
+test("Test NotEndsWithOperator", async (t) => {
+    const op = operatorMap.get(OP_NOT_ENDS_WITH);
+    assert.strictEqual(true, op.test("mx1.example.com", "example.net"));
+    assert.strictEqual(false, op.test("mx1.example.com", "example.com"));
+});
+
+test("Test NumberEqualsOperator", async (t) => {
+    const op = operatorMap.get(OP_NUM_EQUALS);
+    assert.strictEqual(true, op.test(1, 1));
+    assert.strictEqual(true, op.test(1, "1"));
+    assert.strictEqual(false, op.test(1, "2"));
+});
+
+test("Test NumberNotEqualsOperator", async (t) => {
+    const op = operatorMap.get(OP_NUM_NOT_EQUALS);
+    assert.strictEqual(true, op.test(1, "2"));
+    assert.strictEqual(false, op.test(1, "1"));
+});
+
+test("Test LessThanOperator", async (t) => {
+    const op = operatorMap.get(OP_LT);
+    assert.strictEqual(true, op.test(1, 2));
+    assert.strictEqual(true, op.test(1, "2"));
+    assert.strictEqual(false, op.test(1, 1));
+});
+
+test("Test GreaterThanOperator", async (t) => {
+    const op = operatorMap.get(OP_GT);
+    assert.strictEqual(true, op.test(2, 1));
+    assert.strictEqual(true, op.test(2, "1"));
+    assert.strictEqual(false, op.test(1, 1));
+});
+
+test("Test LessThanOrEqualToOperator", async (t) => {
+    const op = operatorMap.get(OP_LTE);
+    assert.strictEqual(true, op.test(1, 1));
+    assert.strictEqual(true, op.test(1, 2));
+    assert.strictEqual(true, op.test(1, "2"));
+    assert.strictEqual(false, op.test(1, 0));
+});
+
+test("Test GreaterThanOrEqualToOperator", async (t) => {
+    const op = operatorMap.get(OP_GTE);
+    assert.strictEqual(true, op.test(1, 1));
+    assert.strictEqual(true, op.test(2, 1));
+    assert.strictEqual(true, op.test(2, "2"));
+    assert.strictEqual(false, op.test(2, 3));
+});
diff --git a/test/e2e/specs/monitor-form.spec.js b/test/e2e/specs/monitor-form.spec.js
new file mode 100644
index 000000000..7efc117c0
--- /dev/null
+++ b/test/e2e/specs/monitor-form.spec.js
@@ -0,0 +1,109 @@
+import { expect, test } from "@playwright/test";
+import { login, restoreSqliteSnapshot, screenshot } from "../util-test";
+
+test.describe("Monitor Form", () => {
+
+    test.beforeEach(async ({ page }) => {
+        await restoreSqliteSnapshot(page);
+    });
+
+    test("condition ui", async ({ page }, testInfo) => {
+        await page.goto("./add");
+        await login(page);
+        await screenshot(testInfo, page);
+
+        const monitorTypeSelect = page.getByTestId("monitor-type-select");
+        await expect(monitorTypeSelect).toBeVisible();
+
+        await monitorTypeSelect.selectOption("dns");
+        const selectedValue = await monitorTypeSelect.evaluate(select => select.value);
+        expect(selectedValue).toBe("dns");
+
+        // Add Conditions & verify:
+        await page.getByTestId("add-condition-button").click();
+        expect(await page.getByTestId("condition").count()).toEqual(2); // 1 added by default + 1 explicitly added
+
+        // Add a Condition Group & verify:
+        await page.getByTestId("add-group-button").click();
+        expect(await page.getByTestId("condition-group").count()).toEqual(1);
+        expect(await page.getByTestId("condition").count()).toEqual(3); // 2 solo conditions + 1 condition in group
+
+        await screenshot(testInfo, page);
+
+        // Remove a condition & verify:
+        await page.getByTestId("remove-condition").first().click();
+        expect(await page.getByTestId("condition").count()).toEqual(2); // 1 solo condition + 1 condition in group
+
+        // Remove a condition group & verify:
+        await page.getByTestId("remove-condition-group").first().click();
+        expect(await page.getByTestId("condition-group").count()).toEqual(0);
+
+        await screenshot(testInfo, page);
+    });
+
+    test("successful condition", async ({ page }, testInfo) => {
+        await page.goto("./add");
+        await login(page);
+        await screenshot(testInfo, page);
+
+        const monitorTypeSelect = page.getByTestId("monitor-type-select");
+        await expect(monitorTypeSelect).toBeVisible();
+
+        await monitorTypeSelect.selectOption("dns");
+        const selectedValue = await monitorTypeSelect.evaluate(select => select.value);
+        expect(selectedValue).toBe("dns");
+
+        const friendlyName = "Example DNS NS";
+        await page.getByTestId("friendly-name-input").fill(friendlyName);
+        await page.getByTestId("hostname-input").fill("example.com");
+
+        // Vue-Multiselect component
+        const resolveTypeSelect = page.getByTestId("resolve-type-select");
+        await resolveTypeSelect.click();
+        await resolveTypeSelect.getByRole("option", { name: "NS" }).click();
+
+        await page.getByTestId("add-condition-button").click();
+        expect(await page.getByTestId("condition").count()).toEqual(2); // 1 added by default + 1 explicitly added
+        await page.getByTestId("condition-value").nth(0).fill("a.iana-servers.net");
+        await page.getByTestId("condition-and-or").nth(0).selectOption("or");
+        await page.getByTestId("condition-value").nth(1).fill("b.iana-servers.net");
+        await screenshot(testInfo, page);
+
+        await page.getByTestId("save-button").click();
+        await page.waitForURL("/dashboard/*"); // wait for the monitor to be created
+        await expect(page.getByTestId("monitor-status")).toHaveText("up", { ignoreCase: true });
+        await screenshot(testInfo, page);
+    });
+
+    test("failing condition", async ({ page }, testInfo) => {
+        await page.goto("./add");
+        await login(page);
+        await screenshot(testInfo, page);
+
+        const monitorTypeSelect = page.getByTestId("monitor-type-select");
+        await expect(monitorTypeSelect).toBeVisible();
+
+        await monitorTypeSelect.selectOption("dns");
+        const selectedValue = await monitorTypeSelect.evaluate(select => select.value);
+        expect(selectedValue).toBe("dns");
+
+        const friendlyName = "Example DNS NS";
+        await page.getByTestId("friendly-name-input").fill(friendlyName);
+        await page.getByTestId("hostname-input").fill("example.com");
+
+        // Vue-Multiselect component
+        const resolveTypeSelect = page.getByTestId("resolve-type-select");
+        await resolveTypeSelect.click();
+        await resolveTypeSelect.getByRole("option", { name: "NS" }).click();
+
+        expect(await page.getByTestId("condition").count()).toEqual(1); // 1 added by default
+        await page.getByTestId("condition-value").nth(0).fill("definitely-not.net");
+        await screenshot(testInfo, page);
+
+        await page.getByTestId("save-button").click();
+        await page.waitForURL("/dashboard/*"); // wait for the monitor to be created
+        await expect(page.getByTestId("monitor-status")).toHaveText("down", { ignoreCase: true });
+        await screenshot(testInfo, page);
+    });
+
+});