diff --git a/README.md b/README.md
index ad479d7b5..a605a6943 100644
--- a/README.md
+++ b/README.md
@@ -266,6 +266,7 @@ The special E2E client settings should be defined in `env.yml`:
 | CONNECTED_DATA_PLATFORM_TRIP_HISTORY_UPLOAD_JOB_FREQUENCY_IN_MINUTES | integer | Optional | 5 | CDP trip history upload frequency. |
 | CONNECTED_DATA_PLATFORM_UPLOAD_BLANK_FILES | boolean | Optional | true | Whether to upload files where no records have been written. Defaults to true. |
 | DEFAULT_USAGE_PLAN_ID | string | Required | 123e45 | AWS API gateway default usage plan used when creating API keys for API users. |
+| MAXIMUM_MONITORED_TRIP_ITINERARY_CHECKS | integer | Optional | 3 | The maximum number of attempts to obtain a monitored trip itinerary. |
 | MAXIMUM_PERMITTED_MONITORED_TRIPS | integer | Optional | 5 | The maximum number of saved monitored trips. |
 | MONGO_DB_NAME | string | Required | otp_middleware | The name of the OTP Middleware Mongo DB. |
 | MONGO_HOST | string | Optional | localhost:27017 | Mongo host address. |
diff --git a/configurations/default/env.yml.tmp b/configurations/default/env.yml.tmp
index 746e021b7..93730bf49 100644
--- a/configurations/default/env.yml.tmp
+++ b/configurations/default/env.yml.tmp
@@ -104,5 +104,8 @@ US_RIDE_GWINNETT_BUS_OPERATOR_NOTIFIER_API_URL: https://bus.notifier.example.com
 US_RIDE_GWINNETT_BUS_OPERATOR_NOTIFIER_API_KEY: your-key
 US_RIDE_GWINNETT_BUS_OPERATOR_NOTIFIER_QUALIFYING_ROUTES: agency_id:route_id
 
+MAXIMUM_MONITORED_TRIP_ITINERARY_CHECKS: 3
+
 # The location for an OTP plan query request.
-PLAN_QUERY_RESOURCE_URI: https://plan.resource.com
\ No newline at end of file
+PLAN_QUERY_RESOURCE_URI: https://plan.resource.com
+
diff --git a/src/main/java/org/opentripplanner/middleware/controllers/api/MonitoredTripController.java b/src/main/java/org/opentripplanner/middleware/controllers/api/MonitoredTripController.java
index f22f60bbb..476e99b11 100644
--- a/src/main/java/org/opentripplanner/middleware/controllers/api/MonitoredTripController.java
+++ b/src/main/java/org/opentripplanner/middleware/controllers/api/MonitoredTripController.java
@@ -104,7 +104,7 @@ MonitoredTrip postCreateHook(MonitoredTrip monitoredTrip, Request req) {
      * monitored trip job, so return the trip as found in the database after the job completes.
      */
     private MonitoredTrip runCheckMonitoredTrip(MonitoredTrip monitoredTrip) throws Exception {
-        new CheckMonitoredTrip(monitoredTrip).run();
+        new CheckMonitoredTrip(monitoredTrip, false).run();
         return Persistence.monitoredTrips.getById(monitoredTrip.id);
     }
 
diff --git a/src/main/java/org/opentripplanner/middleware/models/MonitoredTrip.java b/src/main/java/org/opentripplanner/middleware/models/MonitoredTrip.java
index 382937cdb..6d0e25ef9 100644
--- a/src/main/java/org/opentripplanner/middleware/models/MonitoredTrip.java
+++ b/src/main/java/org/opentripplanner/middleware/models/MonitoredTrip.java
@@ -173,6 +173,11 @@ public class MonitoredTrip extends Model {
      */
     public boolean notifyAtLeadingInterval = true;
 
+    /**
+     * The number of attempts made to obtain a trip's itinerary from OTP which matches this trip.
+     */
+    public int attemptsToGetMatchingItinerary;
+
     public MonitoredTrip() {
     }
 
diff --git a/src/main/java/org/opentripplanner/middleware/tripmonitor/jobs/CheckMonitoredTrip.java b/src/main/java/org/opentripplanner/middleware/tripmonitor/jobs/CheckMonitoredTrip.java
index 3e0fdd1f7..081bbbc66 100644
--- a/src/main/java/org/opentripplanner/middleware/tripmonitor/jobs/CheckMonitoredTrip.java
+++ b/src/main/java/org/opentripplanner/middleware/tripmonitor/jobs/CheckMonitoredTrip.java
@@ -54,6 +54,9 @@ public class CheckMonitoredTrip implements Runnable {
 
     private final String OTP_UI_NAME = ConfigUtils.getConfigPropertyAsText("OTP_UI_NAME");
 
+    public static final int MAXIMUM_MONITORED_TRIP_ITINERARY_CHECKS =
+        ConfigUtils.getConfigPropertyAsInt("MAXIMUM_MONITORED_TRIP_ITINERARY_CHECKS", 3);
+
     private final String ACCOUNT_PATH = "/#/account";
 
     private final String TRIPS_PATH = ACCOUNT_PATH + "/trips";
@@ -113,8 +116,15 @@ public class CheckMonitoredTrip implements Runnable {
     /** The OTP Response provider */
     private Supplier<OtpResponse> otpResponseProvider;
 
+    private final boolean hasTolerantItineraryCheck;
+
     public CheckMonitoredTrip(MonitoredTrip trip) throws CloneNotSupportedException {
+        this(trip, true);
+    }
+
+    public CheckMonitoredTrip(MonitoredTrip trip, boolean hasTolerantItineraryCheck) throws CloneNotSupportedException {
         this.trip = trip;
+        this.hasTolerantItineraryCheck = hasTolerantItineraryCheck;
         previousJourneyState = trip.journeyState;
         journeyState = previousJourneyState.clone();
         previousMatchingItinerary = trip.journeyState.matchingItinerary;
@@ -122,7 +132,16 @@ public CheckMonitoredTrip(MonitoredTrip trip) throws CloneNotSupportedException
     }
 
     public CheckMonitoredTrip(MonitoredTrip trip, Supplier<OtpResponse> otpResponseProvider) throws CloneNotSupportedException {
-        this(trip);
+        this(trip, false);
+        this.otpResponseProvider = otpResponseProvider;
+    }
+
+    public CheckMonitoredTrip(
+        MonitoredTrip trip,
+        Supplier<OtpResponse> otpResponseProvider,
+        boolean hasTolerantItineraryCheck
+    ) throws CloneNotSupportedException {
+        this(trip, hasTolerantItineraryCheck);
         this.otpResponseProvider = otpResponseProvider;
     }
 
@@ -246,6 +265,7 @@ private boolean makeOTPRequestAndUpdateMatchingItineraryInternal() {
             if (ItineraryUtils.itinerariesMatch(trip.itinerary, candidateItinerary)) {
                 // matching itinerary found!
                 LOG.info("Found matching itinerary!");
+                trip.attemptsToGetMatchingItinerary = 0;
 
                 // Set the matching itinerary.
                 matchingItinerary = candidateItinerary;
@@ -283,40 +303,68 @@ private boolean makeOTPRequestAndUpdateMatchingItineraryInternal() {
         // If this point is reached, a matching itinerary was not found
         LOG.warn("No comparison itinerary found in otp response for trip");
 
-        // Check whether this trip should no longer ever be checked due to not having matching itineraries on any
-        // monitored day of the week. For trips that are only monitored on one day of the week, they could have been not
-        // possible for just that day, but could again be possible the next week. Therefore, this checks if the trip
-        // was not possible on all monitored days of the previous week and if so, it updates the journeyState to say
-        // that the trip is no longer possible.
-        boolean noMatchingItineraryFoundOnPreviousChecks =
-            !trip.itineraryExistence.isPossibleOnAtLeastOneMonitoredDayOfTheWeek(trip);
-        journeyState.tripStatus = noMatchingItineraryFoundOnPreviousChecks
-            ? TripStatus.NO_LONGER_POSSIBLE
-            : TripStatus.NEXT_TRIP_NOT_POSSIBLE;
+        if (hasReachedMaxItineraryChecks()) {
+            // Check whether this trip should no longer ever be checked due to not having matching itineraries on any
+            // monitored day of the week. For trips that are only monitored on one day of the week, they could have been not
+            // possible for just that day, but could again be possible the next week. Therefore, this checks if the trip
+            // was not possible on all monitored days of the previous week and if so, it updates the journeyState to say
+            // that the trip is no longer possible.
+            boolean noMatchingItineraryFoundOnPreviousChecks =
+                !trip.itineraryExistence.isPossibleOnAtLeastOneMonitoredDayOfTheWeek(trip);
+            journeyState.tripStatus = noMatchingItineraryFoundOnPreviousChecks
+                ? TripStatus.NO_LONGER_POSSIBLE
+                : TripStatus.NEXT_TRIP_NOT_POSSIBLE;
 
-        LOG.info(
-            noMatchingItineraryFoundOnPreviousChecks
-                ? "Trip checking has no more possible days to check, TRIP NO LONGER POSSIBLE!"
-                : "Trip is not possible today, will check again next week."
-        );
+            LOG.info(
+                noMatchingItineraryFoundOnPreviousChecks
+                    ? "Trip checking has no more possible days to check, TRIP NO LONGER POSSIBLE!"
+                    : "Trip is not possible today, will check again next week."
+            );
 
-        // update trip itinerary existence to reflect that trip was not possible on this day of the week
-        trip.itineraryExistence
-            .getResultForDayOfWeek(targetZonedDateTime.getDayOfWeek())
-            .handleInvalidDate(targetZonedDateTime);
-        updateMonitoredTrip();
+            // update trip itinerary existence to reflect that trip was not possible on this day of the week
+            trip.itineraryExistence
+                .getResultForDayOfWeek(targetZonedDateTime.getDayOfWeek())
+                .handleInvalidDate(targetZonedDateTime);
+            updateMonitoredTrip();
 
-        // send an appropriate notification if the trip is still possible on another day of the week, or if it is now
-        // not possible on any day of the week that the trip should be monitored
-        enqueueNotification(
-            TripMonitorNotification.createItineraryNotFoundNotification(
-                !noMatchingItineraryFoundOnPreviousChecks,
-                getOtpUserLocale()
-            )
-        );
+            // send an appropriate notification if the trip is still possible on another day of the week, or if it is now
+            // not possible on any day of the week that the trip should be monitored
+            enqueueNotification(
+                TripMonitorNotification.createItineraryNotFoundNotification(
+                    !noMatchingItineraryFoundOnPreviousChecks,
+                    getOtpUserLocale()
+                )
+            );
+        }
         return false;
     }
 
+    /**
+     * If the OTP response does not contain the expected itinerary, check the number of attempts made and decide whether
+     * to try again or stop checking.
+     */
+    private boolean hasReachedMaxItineraryChecks() {
+        if (!hasTolerantItineraryCheck) {
+            LOG.info("Tolerant itinerary check disabled.");
+            return true;
+        }
+        trip.attemptsToGetMatchingItinerary++;
+        LOG.info(
+            "Attempt {} of {} to get matching itinerary.",
+            trip.attemptsToGetMatchingItinerary,
+            MAXIMUM_MONITORED_TRIP_ITINERARY_CHECKS
+        );
+        if (trip.attemptsToGetMatchingItinerary < MAXIMUM_MONITORED_TRIP_ITINERARY_CHECKS) {
+            if (Persistence.monitoredTrips.getById(trip.id) == null) {
+                // Trip has been deleted. Continue as if maximum itinerary checks have been reached.
+                return true;
+            }
+            Persistence.monitoredTrips.replace(trip.id, trip);
+            return false;
+        }
+        return true;
+    }
+
     /** Default implementation for OtpResponse provider that actually invokes the OTP server. */
     private OtpResponse getOtpResponse() {
         return OtpDispatcher.sendOtpRequestWithErrorHandling(getQueryParamsForTargetZonedDateTime());
diff --git a/src/main/resources/env.schema.json b/src/main/resources/env.schema.json
index 715cef056..fcc9f79f8 100644
--- a/src/main/resources/env.schema.json
+++ b/src/main/resources/env.schema.json
@@ -128,6 +128,11 @@
       "examples": ["123e45"],
       "description": "AWS API gateway default usage plan used when creating API keys for API users."
     },
+    "MAXIMUM_MONITORED_TRIP_ITINERARY_CHECKS": {
+      "type": "integer",
+      "examples": ["3"],
+      "description": "The maximum number of attempts to obtain a monitored trip itinerary."
+    },
     "MAXIMUM_PERMITTED_MONITORED_TRIPS": {
       "type": "integer",
       "examples": ["5"],
diff --git a/src/main/resources/latest-spark-swagger-output.yaml b/src/main/resources/latest-spark-swagger-output.yaml
index 009779b5c..0e0f1348c 100644
--- a/src/main/resources/latest-spark-swagger-output.yaml
+++ b/src/main/resources/latest-spark-swagger-output.yaml
@@ -56,10 +56,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/AdminUser"
           schema:
             $ref: "#/definitions/AdminUser"
+          responseSchema:
+            $ref: "#/definitions/AdminUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -90,10 +90,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/AdminUser"
           schema:
             $ref: "#/definitions/AdminUser"
+          responseSchema:
+            $ref: "#/definitions/AdminUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -123,10 +123,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/Job"
           schema:
             $ref: "#/definitions/Job"
+          responseSchema:
+            $ref: "#/definitions/Job"
   /api/admin/user:
     get:
       tags:
@@ -155,10 +155,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/ResponseList"
           schema:
             $ref: "#/definitions/ResponseList"
+          responseSchema:
+            $ref: "#/definitions/ResponseList"
     post:
       tags:
       - "api/admin/user"
@@ -178,10 +178,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/AdminUser"
           schema:
             $ref: "#/definitions/AdminUser"
+          responseSchema:
+            $ref: "#/definitions/AdminUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -220,10 +220,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/AdminUser"
           schema:
             $ref: "#/definitions/AdminUser"
+          responseSchema:
+            $ref: "#/definitions/AdminUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -269,10 +269,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/AdminUser"
           schema:
             $ref: "#/definitions/AdminUser"
+          responseSchema:
+            $ref: "#/definitions/AdminUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -309,10 +309,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/AdminUser"
           schema:
             $ref: "#/definitions/AdminUser"
+          responseSchema:
+            $ref: "#/definitions/AdminUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -356,10 +356,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/ApiUser"
           schema:
             $ref: "#/definitions/ApiUser"
+          responseSchema:
+            $ref: "#/definitions/ApiUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -402,10 +402,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/ApiUser"
           schema:
             $ref: "#/definitions/ApiUser"
+          responseSchema:
+            $ref: "#/definitions/ApiUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -447,10 +447,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/TokenHolder"
           schema:
             $ref: "#/definitions/TokenHolder"
+          responseSchema:
+            $ref: "#/definitions/TokenHolder"
   /api/secure/application/fromtoken:
     get:
       tags:
@@ -464,10 +464,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/ApiUser"
           schema:
             $ref: "#/definitions/ApiUser"
+          responseSchema:
+            $ref: "#/definitions/ApiUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -498,10 +498,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/ApiUser"
           schema:
             $ref: "#/definitions/ApiUser"
+          responseSchema:
+            $ref: "#/definitions/ApiUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -531,10 +531,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/Job"
           schema:
             $ref: "#/definitions/Job"
+          responseSchema:
+            $ref: "#/definitions/Job"
   /api/secure/application:
     get:
       tags:
@@ -563,10 +563,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/ResponseList"
           schema:
             $ref: "#/definitions/ResponseList"
+          responseSchema:
+            $ref: "#/definitions/ResponseList"
     post:
       tags:
       - "api/secure/application"
@@ -586,10 +586,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/ApiUser"
           schema:
             $ref: "#/definitions/ApiUser"
+          responseSchema:
+            $ref: "#/definitions/ApiUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -628,10 +628,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/ApiUser"
           schema:
             $ref: "#/definitions/ApiUser"
+          responseSchema:
+            $ref: "#/definitions/ApiUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -677,10 +677,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/ApiUser"
           schema:
             $ref: "#/definitions/ApiUser"
+          responseSchema:
+            $ref: "#/definitions/ApiUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -717,10 +717,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/ApiUser"
           schema:
             $ref: "#/definitions/ApiUser"
+          responseSchema:
+            $ref: "#/definitions/ApiUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -754,10 +754,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/CDPUser"
           schema:
             $ref: "#/definitions/CDPUser"
+          responseSchema:
+            $ref: "#/definitions/CDPUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -788,10 +788,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/CDPUser"
           schema:
             $ref: "#/definitions/CDPUser"
+          responseSchema:
+            $ref: "#/definitions/CDPUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -821,10 +821,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/Job"
           schema:
             $ref: "#/definitions/Job"
+          responseSchema:
+            $ref: "#/definitions/Job"
   /api/secure/cdp:
     get:
       tags:
@@ -853,10 +853,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/ResponseList"
           schema:
             $ref: "#/definitions/ResponseList"
+          responseSchema:
+            $ref: "#/definitions/ResponseList"
     post:
       tags:
       - "api/secure/cdp"
@@ -876,10 +876,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/CDPUser"
           schema:
             $ref: "#/definitions/CDPUser"
+          responseSchema:
+            $ref: "#/definitions/CDPUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -918,10 +918,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/CDPUser"
           schema:
             $ref: "#/definitions/CDPUser"
+          responseSchema:
+            $ref: "#/definitions/CDPUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -967,10 +967,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/CDPUser"
           schema:
             $ref: "#/definitions/CDPUser"
+          responseSchema:
+            $ref: "#/definitions/CDPUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1007,10 +1007,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/CDPUser"
           schema:
             $ref: "#/definitions/CDPUser"
+          responseSchema:
+            $ref: "#/definitions/CDPUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1050,10 +1050,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/ItineraryExistence"
           schema:
             $ref: "#/definitions/ItineraryExistence"
+          responseSchema:
+            $ref: "#/definitions/ItineraryExistence"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1102,10 +1102,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/ResponseList"
           schema:
             $ref: "#/definitions/ResponseList"
+          responseSchema:
+            $ref: "#/definitions/ResponseList"
     post:
       tags:
       - "api/secure/monitoredtrip"
@@ -1125,10 +1125,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/MonitoredTrip"
           schema:
             $ref: "#/definitions/MonitoredTrip"
+          responseSchema:
+            $ref: "#/definitions/MonitoredTrip"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1167,10 +1167,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/MonitoredTrip"
           schema:
             $ref: "#/definitions/MonitoredTrip"
+          responseSchema:
+            $ref: "#/definitions/MonitoredTrip"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1216,10 +1216,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/MonitoredTrip"
           schema:
             $ref: "#/definitions/MonitoredTrip"
+          responseSchema:
+            $ref: "#/definitions/MonitoredTrip"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1257,10 +1257,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/MonitoredTrip"
           schema:
             $ref: "#/definitions/MonitoredTrip"
+          responseSchema:
+            $ref: "#/definitions/MonitoredTrip"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1298,10 +1298,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/TrackingResponse"
           schema:
             $ref: "#/definitions/TrackingResponse"
+          responseSchema:
+            $ref: "#/definitions/TrackingResponse"
   /api/secure/monitoredtrip/updatetracking:
     post:
       tags:
@@ -1319,10 +1319,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/TrackingResponse"
           schema:
             $ref: "#/definitions/TrackingResponse"
+          responseSchema:
+            $ref: "#/definitions/TrackingResponse"
   /api/secure/monitoredtrip/track:
     post:
       tags:
@@ -1340,10 +1340,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/TrackingResponse"
           schema:
             $ref: "#/definitions/TrackingResponse"
+          responseSchema:
+            $ref: "#/definitions/TrackingResponse"
   /api/secure/monitoredtrip/endtracking:
     post:
       tags:
@@ -1361,10 +1361,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/EndTrackingResponse"
           schema:
             $ref: "#/definitions/EndTrackingResponse"
+          responseSchema:
+            $ref: "#/definitions/EndTrackingResponse"
   /api/secure/monitoredtrip/forciblyendtracking:
     post:
       tags:
@@ -1382,10 +1382,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/EndTrackingResponse"
           schema:
             $ref: "#/definitions/EndTrackingResponse"
+          responseSchema:
+            $ref: "#/definitions/EndTrackingResponse"
   /api/secure/triprequests:
     get:
       tags:
@@ -1430,10 +1430,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/TripRequest"
           schema:
             $ref: "#/definitions/TripRequest"
+          responseSchema:
+            $ref: "#/definitions/TripRequest"
   /api/secure/monitoredcomponent:
     get:
       tags:
@@ -1462,10 +1462,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/ResponseList"
           schema:
             $ref: "#/definitions/ResponseList"
+          responseSchema:
+            $ref: "#/definitions/ResponseList"
     post:
       tags:
       - "api/secure/monitoredcomponent"
@@ -1485,10 +1485,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/MonitoredComponent"
           schema:
             $ref: "#/definitions/MonitoredComponent"
+          responseSchema:
+            $ref: "#/definitions/MonitoredComponent"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1527,10 +1527,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/MonitoredComponent"
           schema:
             $ref: "#/definitions/MonitoredComponent"
+          responseSchema:
+            $ref: "#/definitions/MonitoredComponent"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1576,10 +1576,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/MonitoredComponent"
           schema:
             $ref: "#/definitions/MonitoredComponent"
+          responseSchema:
+            $ref: "#/definitions/MonitoredComponent"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1617,10 +1617,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/MonitoredComponent"
           schema:
             $ref: "#/definitions/MonitoredComponent"
+          responseSchema:
+            $ref: "#/definitions/MonitoredComponent"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1660,10 +1660,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/VerificationResult"
           schema:
             $ref: "#/definitions/VerificationResult"
+          responseSchema:
+            $ref: "#/definitions/VerificationResult"
   /api/secure/user/{id}/verify_sms/{code}:
     post:
       tags:
@@ -1683,10 +1683,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/VerificationResult"
           schema:
             $ref: "#/definitions/VerificationResult"
+          responseSchema:
+            $ref: "#/definitions/VerificationResult"
   /api/secure/user/fromtoken:
     get:
       tags:
@@ -1700,10 +1700,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/OtpUser"
           schema:
             $ref: "#/definitions/OtpUser"
+          responseSchema:
+            $ref: "#/definitions/OtpUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1734,10 +1734,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/OtpUser"
           schema:
             $ref: "#/definitions/OtpUser"
+          responseSchema:
+            $ref: "#/definitions/OtpUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1767,10 +1767,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/Job"
           schema:
             $ref: "#/definitions/Job"
+          responseSchema:
+            $ref: "#/definitions/Job"
   /api/secure/user:
     get:
       tags:
@@ -1799,10 +1799,10 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
-            $ref: "#/definitions/ResponseList"
           schema:
             $ref: "#/definitions/ResponseList"
+          responseSchema:
+            $ref: "#/definitions/ResponseList"
     post:
       tags:
       - "api/secure/user"
@@ -1822,10 +1822,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/OtpUser"
           schema:
             $ref: "#/definitions/OtpUser"
+          responseSchema:
+            $ref: "#/definitions/OtpUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1864,10 +1864,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/OtpUser"
           schema:
             $ref: "#/definitions/OtpUser"
+          responseSchema:
+            $ref: "#/definitions/OtpUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1913,10 +1913,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/OtpUser"
           schema:
             $ref: "#/definitions/OtpUser"
+          responseSchema:
+            $ref: "#/definitions/OtpUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -1953,10 +1953,10 @@ paths:
         "200":
           description: "Successful operation"
           examples: {}
-          responseSchema:
-            $ref: "#/definitions/OtpUser"
           schema:
             $ref: "#/definitions/OtpUser"
+          responseSchema:
+            $ref: "#/definitions/OtpUser"
         "400":
           description: "The request was not formed properly (e.g., some required parameters\
             \ may be missing). See the details of the returned response to determine\
@@ -2010,11 +2010,11 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
+          schema:
             type: "array"
             items:
               $ref: "#/definitions/ApiUsageResult"
-          schema:
+          responseSchema:
             type: "array"
             items:
               $ref: "#/definitions/ApiUsageResult"
@@ -2041,11 +2041,11 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
+          schema:
             type: "array"
             items:
               $ref: "#/definitions/BugsnagEvent"
-          schema:
+          responseSchema:
             type: "array"
             items:
               $ref: "#/definitions/BugsnagEvent"
@@ -2072,11 +2072,11 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
+          schema:
             type: "array"
             items:
               $ref: "#/definitions/CDPFile"
-          schema:
+          responseSchema:
             type: "array"
             items:
               $ref: "#/definitions/CDPFile"
@@ -2097,11 +2097,11 @@ paths:
       responses:
         "200":
           description: "successful operation"
-          responseSchema:
+          schema:
             type: "array"
             items:
               $ref: "#/definitions/URL"
-          schema:
+          responseSchema:
             type: "array"
             items:
               $ref: "#/definitions/URL"
@@ -2566,6 +2566,9 @@ definitions:
         $ref: "#/definitions/JourneyState"
       notifyAtLeadingInterval:
         type: "boolean"
+      attemptsToGetMatchingItinerary:
+        type: "integer"
+        format: "int32"
   StopTime:
     type: "object"
     properties:
diff --git a/src/test/java/org/opentripplanner/middleware/tripmonitor/jobs/CheckMonitoredTripTest.java b/src/test/java/org/opentripplanner/middleware/tripmonitor/jobs/CheckMonitoredTripTest.java
index 5986a74d6..9bc9a3eb6 100644
--- a/src/test/java/org/opentripplanner/middleware/tripmonitor/jobs/CheckMonitoredTripTest.java
+++ b/src/test/java/org/opentripplanner/middleware/tripmonitor/jobs/CheckMonitoredTripTest.java
@@ -47,6 +47,8 @@
 import static org.junit.jupiter.api.Assertions.assertNotNull;
 import static org.junit.jupiter.api.Assertions.assertNull;
 import static org.junit.jupiter.api.Assertions.assertTrue;
+import static org.opentripplanner.middleware.tripmonitor.TripStatus.NEXT_TRIP_NOT_POSSIBLE;
+import static org.opentripplanner.middleware.tripmonitor.TripStatus.TRIP_ACTIVE;
 import static org.opentripplanner.middleware.tripmonitor.jobs.CheckMonitoredTripBasicTest.makeMonitoredTripFromNow;
 import static org.opentripplanner.middleware.tripmonitor.jobs.CheckMonitoredTripBasicTest.setRecurringTodayAndTomorrow;
 
@@ -408,7 +410,7 @@ void canMakeOTPRequestAndUpdateMatchingItineraryForPreviouslyUnmatchedItinerary(
 
         // verify that status is active
         assertEquals(
-            TripStatus.TRIP_ACTIVE,
+            TRIP_ACTIVE,
             updatedTrip.journeyState.tripStatus,
             "updated trips status should be active"
         );
@@ -473,7 +475,7 @@ void canMakeOTPRequestAndResolveUnmatchedItinerary() throws Exception {
 
         // verify that status is active
         assertEquals(
-            TripStatus.NEXT_TRIP_NOT_POSSIBLE,
+            NEXT_TRIP_NOT_POSSIBLE,
             updatedTrip.journeyState.tripStatus,
             "updated trips status should indicate trip is not possible this day"
         );
@@ -550,7 +552,7 @@ void canMakeOTPRequestAndResolveNoLongerPossibleTrip() throws Exception {
         // fetch updated trip from persistence
         MonitoredTrip updatedTrip = Persistence.monitoredTrips.getById(mockTrip.id);
 
-        // verify that status is active
+        // verify that trip status is no longer possible
         assertEquals(
             TripStatus.NO_LONGER_POSSIBLE,
             updatedTrip.journeyState.tripStatus,
@@ -580,7 +582,7 @@ void canMakeOTPRequestAndResolveNoLongerPossibleTrip() throws Exception {
     void shouldReportOneTimeTripInPastAsCompleted() throws CloneNotSupportedException {
         MonitoredTrip trip = makeMonitoredTripFromNow(-900, -300);
         trip.journeyState.matchingItinerary = trip.itinerary;
-        trip.journeyState.tripStatus = TripStatus.TRIP_ACTIVE;
+        trip.journeyState.tripStatus = TRIP_ACTIVE;
 
         new CheckMonitoredTrip(trip, this::mockOtpPlanResponse).checkOtpAndUpdateTripStatus();
         assertEquals(TripStatus.PAST_TRIP, trip.journeyState.tripStatus);
@@ -591,7 +593,7 @@ void shouldReportOneTimeTripInPastWithTrackingAsActive() throws CloneNotSupporte
         MonitoredTrip trip = createPastActiveTripWithTrackedJourney();
 
         new CheckMonitoredTrip(trip, this::mockOtpPlanResponse).checkOtpAndUpdateTripStatus();
-        assertEquals(TripStatus.TRIP_ACTIVE, trip.journeyState.tripStatus);
+        assertEquals(TRIP_ACTIVE, trip.journeyState.tripStatus);
     }
 
     private static MonitoredTrip createPastActiveTripWithTrackedJourney() {
@@ -614,7 +616,7 @@ private static MonitoredTrip createPastActiveTrip() {
         trip.userId = user.id;
         trip.journeyState.matchingItinerary = trip.itinerary;
         trip.journeyState.targetDate = todayFormatted;
-        trip.journeyState.tripStatus = TripStatus.TRIP_ACTIVE;
+        trip.journeyState.tripStatus = TRIP_ACTIVE;
         Persistence.monitoredTrips.create(trip);
         return trip;
     }
@@ -647,7 +649,7 @@ void shouldReportRecurringTripInstanceInPastWithTrackingAsActive() throws Except
         check.shouldSkipMonitoredTripCheck(false);
         check.checkOtpAndUpdateTripStatus();
         // Trip should remain active, and the target date should still be "today".
-        assertEquals(TripStatus.TRIP_ACTIVE, trip.journeyState.tripStatus);
+        assertEquals(TRIP_ACTIVE, trip.journeyState.tripStatus);
         assertEquals(todayFormatted, trip.journeyState.targetDate);
     }
 
@@ -656,4 +658,92 @@ static String getShiftedDay(Date startTime, int dayShift) {
         Date nextDayStart = Date.from(startInstant.plus(dayShift, ChronoUnit.DAYS));
         return DateTimeUtils.makeOtpZonedDateTime(nextDayStart).format(DateTimeFormatter.ISO_LOCAL_DATE);
     }
+
+    @Test
+    void canBeTolerantWithItineraryChecks() throws Exception {
+        MonitoredTrip monitoredTrip = PersistenceTestUtils.createMonitoredTrip(
+            user.id,
+            OtpTestUtils.OTP2_DISPATCHER_PLAN_RESPONSE.clone(),
+            false,
+            OtpTestUtils.createDefaultJourneyState()
+        );
+        monitoredTrip.itineraryExistence.monday = new ItineraryExistence.ItineraryExistenceResult();
+        Persistence.monitoredTrips.create(monitoredTrip);
+
+        OtpResponse expectedResponse = getMockOtpResponse();
+        OtpResponse unexpectedResponse = getMockOtpResponse();
+        // Remove the final itinerary leg so that the matching itineraries check fails.
+        unexpectedResponse.plan.itineraries.get(0).legs.remove(2);
+
+        // Mock the current time to be 8:45am on Monday, June 15, 2020.
+        DateTimeUtils.useFixedClockAt(
+            noonMonday8June2020
+                .withDayOfMonth(15)
+                .withHour(8)
+                .withMinute(45)
+        );
+
+        // Match on first attempts.
+        assertCheckMonitoredTrip(monitoredTrip, expectedResponse, true, 0, TRIP_ACTIVE);
+        assertCheckMonitoredTrip(monitoredTrip, expectedResponse, false, 0, TRIP_ACTIVE);
+
+        // Fail on first attempt.
+        assertCheckMonitoredTrip(monitoredTrip, unexpectedResponse, false, 0, NEXT_TRIP_NOT_POSSIBLE);
+
+        // Reactivate trip.
+        monitoredTrip.journeyState.tripStatus = TRIP_ACTIVE;
+        Persistence.monitoredTrips.replace(monitoredTrip.id, monitoredTrip);
+
+        // Match on second attempt.
+        assertCheckMonitoredTrip(monitoredTrip, unexpectedResponse, true, 1, TRIP_ACTIVE);
+        assertCheckMonitoredTrip(monitoredTrip, expectedResponse, true, 0, TRIP_ACTIVE);
+
+        // Match on third attempt.
+        for (int i = 1; i <= 3; i++) {
+            int expectedAttempts = (i < 3) ? i : 0;
+            OtpResponse response = (i < 3) ? unexpectedResponse : expectedResponse;
+            assertCheckMonitoredTrip(monitoredTrip, response, true, expectedAttempts, TRIP_ACTIVE);
+        }
+
+        int maxChecks = CheckMonitoredTrip.MAXIMUM_MONITORED_TRIP_ITINERARY_CHECKS;
+
+        // Fail after maximum checks have been reached.
+        for (int i = 1; i <= maxChecks; i++) {
+            TripStatus tripStatus = (i < maxChecks) ? TRIP_ACTIVE : NEXT_TRIP_NOT_POSSIBLE;
+            assertCheckMonitoredTrip(monitoredTrip, unexpectedResponse, true, i, tripStatus);
+        }
+
+        // Clear the created trip.
+        PersistenceTestUtils.deleteMonitoredTrip(monitoredTrip);
+    }
+
+    /**
+     * Create mock OTP response and set the base times of the first itinerary to Monday, June 15, 2020.
+     */
+    private OtpResponse getMockOtpResponse() {
+        OtpResponse mockResponse = mockOtpPlanResponse();
+        Itinerary mockMondayJune15Itinerary = mockResponse.plan.itineraries.get(0);
+        OtpTestUtils.updateBaseItineraryTime(
+            mockMondayJune15Itinerary,
+            DateTimeUtils.makeOtpZonedDateTime(mockMondayJune15Itinerary.startTime)
+                .withDayOfMonth(15)
+        );
+        return mockResponse;
+    }
+
+    /**
+     * Run check on monitored trip and confirm expected state.
+     */
+    private void assertCheckMonitoredTrip(
+        MonitoredTrip monitoredTrip,
+        OtpResponse mockResponse,
+        boolean hasTolerantItineraryCheck,
+        int expectedAttempts,
+        TripStatus expectedTripStatus
+    ) throws CloneNotSupportedException {
+        CheckMonitoredTrip checkMonitoredTrip = new CheckMonitoredTrip(monitoredTrip, () -> mockResponse, hasTolerantItineraryCheck);
+        checkMonitoredTrip.run();
+        assertEquals(expectedAttempts, monitoredTrip.attemptsToGetMatchingItinerary);
+        assertEquals(expectedTripStatus, monitoredTrip.journeyState.tripStatus);
+    }
 }