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 49b854425..6a5877510 100644
--- a/src/main/java/org/opentripplanner/middleware/controllers/api/MonitoredTripController.java
+++ b/src/main/java/org/opentripplanner/middleware/controllers/api/MonitoredTripController.java
@@ -9,10 +9,12 @@
 import org.opentripplanner.middleware.models.MonitoredTrip;
 import org.opentripplanner.middleware.models.OtpUser;
 import org.opentripplanner.middleware.persistence.Persistence;
+import org.opentripplanner.middleware.models.RelatedUser;
 import org.opentripplanner.middleware.tripmonitor.jobs.CheckMonitoredTrip;
 import org.opentripplanner.middleware.tripmonitor.jobs.MonitoredTripLocks;
 import org.opentripplanner.middleware.utils.InvalidItineraryReason;
 import org.opentripplanner.middleware.utils.JsonUtils;
+import org.opentripplanner.middleware.utils.NotificationUtils;
 import org.opentripplanner.middleware.utils.SwaggerUtils;
 import spark.Request;
 import spark.Response;
@@ -22,12 +24,17 @@
 
 import static io.github.manusant.ss.descriptor.MethodDescriptor.path;
 import static com.mongodb.client.model.Filters.eq;
+import static org.opentripplanner.middleware.i18n.Message.TRIP_INVITE_COMPANION;
+import static org.opentripplanner.middleware.i18n.Message.TRIP_INVITE_OBSERVER;
+import static org.opentripplanner.middleware.i18n.Message.TRIP_INVITE_PRIMARY_TRAVELER;
 import static org.opentripplanner.middleware.models.MonitoredTrip.USER_ID_FIELD_NAME;
+import static org.opentripplanner.middleware.models.MonitoredTrip.getAddedUsers;
 import static org.opentripplanner.middleware.utils.ConfigUtils.getConfigPropertyAsInt;
 import static org.opentripplanner.middleware.utils.HttpUtils.JSON_ONLY;
 import static org.opentripplanner.middleware.utils.JsonUtils.getPOJOFromRequestBody;
 import static org.opentripplanner.middleware.utils.JsonUtils.logMessageAndHalt;
 
+
 /**
  * Implementation of the {@link ApiController} abstract class for managing {@link MonitoredTrip} entities. This
  * controller connects with Auth0 services using the hooks provided by {@link ApiController}.
@@ -90,6 +97,8 @@ MonitoredTrip preCreateHook(MonitoredTrip monitoredTrip, Request req) {
             }
         }
 
+        notifyTripCompanionsAndObservers(monitoredTrip, null);
+
         return monitoredTrip;
     }
 
@@ -128,6 +137,30 @@ private void preCreateOrUpdateChecks(MonitoredTrip monitoredTrip, Request req) {
         processTripQueryParams(monitoredTrip, req);
     }
 
+    /** Notify users added as companions or observers to a trip. (Removed users won't get notified.) */
+    private void notifyTripCompanionsAndObservers(MonitoredTrip monitoredTrip, MonitoredTrip originalTrip) {
+        MonitoredTrip.TripUsers usersToNotify = getAddedUsers(monitoredTrip, originalTrip);
+        OtpUser tripCreator = Persistence.otpUsers.getById(monitoredTrip.userId);
+
+        if (usersToNotify.companion != null) {
+            OtpUser companionUser = Persistence.otpUsers.getOneFiltered(Filters.eq("email", usersToNotify.companion.email));
+            NotificationUtils.notifyCompanion(monitoredTrip, tripCreator, companionUser, TRIP_INVITE_COMPANION);
+        }
+
+        if (usersToNotify.primary != null) {
+            // email could be used too for primary users
+            OtpUser primaryUser = Persistence.otpUsers.getById(usersToNotify.primary.userId);
+            NotificationUtils.notifyCompanion(monitoredTrip, tripCreator, primaryUser, TRIP_INVITE_PRIMARY_TRAVELER);
+        }
+
+        if (!usersToNotify.observers.isEmpty()) {
+            for (RelatedUser observer : usersToNotify.observers) {
+                OtpUser observerUser = Persistence.otpUsers.getOneFiltered(Filters.eq("email", observer.email));
+                NotificationUtils.notifyCompanion(monitoredTrip, tripCreator, observerUser, TRIP_INVITE_OBSERVER);
+            }
+        }
+    }
+
     /**
      * Processes the {@link MonitoredTrip} query parameters, so the trip's fields match the query parameters.
      * If an error occurs regarding the query params, returns a HTTP 400 status.
@@ -171,6 +204,9 @@ MonitoredTrip preUpdateHook(MonitoredTrip monitoredTrip, MonitoredTrip preExisti
             // perform the database update here before releasing the lock to be sure that the record is updated in the
             // database before a CheckMonitoredTripJob analyzes the data
             Persistence.monitoredTrips.replace(monitoredTrip.id, monitoredTrip);
+
+            notifyTripCompanionsAndObservers(monitoredTrip, preExisting);
+
             return runCheckMonitoredTrip(monitoredTrip);
         } catch (Exception e) {
             // FIXME: an error happened while updating the trip, but the trip might have been saved to the DB, so return
diff --git a/src/main/java/org/opentripplanner/middleware/i18n/Message.java b/src/main/java/org/opentripplanner/middleware/i18n/Message.java
index 1870b5dc1..5449885b2 100644
--- a/src/main/java/org/opentripplanner/middleware/i18n/Message.java
+++ b/src/main/java/org/opentripplanner/middleware/i18n/Message.java
@@ -44,6 +44,9 @@ public enum Message {
     TRIP_DELAY_EARLY,
     TRIP_DELAY_LATE,
     TRIP_DELAY_MINUTES,
+    TRIP_INVITE_COMPANION,
+    TRIP_INVITE_PRIMARY_TRAVELER,
+    TRIP_INVITE_OBSERVER,
     TRIP_NOT_FOUND_NOTIFICATION,
     TRIP_NO_LONGER_POSSIBLE_NOTIFICATION,
     TRIP_REMINDER_NOTIFICATION,
diff --git a/src/main/java/org/opentripplanner/middleware/models/AbstractUser.java b/src/main/java/org/opentripplanner/middleware/models/AbstractUser.java
index 7164e3491..16ea0ab6f 100644
--- a/src/main/java/org/opentripplanner/middleware/models/AbstractUser.java
+++ b/src/main/java/org/opentripplanner/middleware/models/AbstractUser.java
@@ -1,6 +1,7 @@
 package org.opentripplanner.middleware.models;
 
 import com.auth0.exception.Auth0Exception;
+import com.fasterxml.jackson.annotation.JsonIgnoreProperties;
 import org.opentripplanner.middleware.auth.Auth0Connection;
 import org.opentripplanner.middleware.auth.RequestingUser;
 import org.opentripplanner.middleware.auth.Permission;
@@ -19,6 +20,7 @@
  * It provides a place to centralize common fields that all users share (e.g., email) and common methods (such as the
  * authorization check {@link #canBeManagedBy}.
  */
+@JsonIgnoreProperties(ignoreUnknown = true)
 public abstract class AbstractUser extends Model {
     private static final Logger LOG = LoggerFactory.getLogger(AbstractUser.class);
     private static final long serialVersionUID = 1L;
diff --git a/src/main/java/org/opentripplanner/middleware/models/MonitoredTrip.java b/src/main/java/org/opentripplanner/middleware/models/MonitoredTrip.java
index b688282c1..4a49703a5 100644
--- a/src/main/java/org/opentripplanner/middleware/models/MonitoredTrip.java
+++ b/src/main/java/org/opentripplanner/middleware/models/MonitoredTrip.java
@@ -27,7 +27,10 @@
 import java.time.ZonedDateTime;
 import java.util.ArrayList;
 import java.util.List;
+import java.util.Objects;
+import java.util.Set;
 import java.util.function.Function;
+import java.util.stream.Collectors;
 
 /**
  * A monitored trip represents a trip a user would like to receive notification on if affected by a delay and/or route
@@ -432,6 +435,69 @@ public boolean isOneTime() {
      * @return true if the trip has a (confirmed) companion, false otherwise.
      */
     public boolean hasConfirmedCompanion() {
-        return companion != null && companion.status == RelatedUser.RelatedUserStatus.CONFIRMED;
+        return companion != null && companion.isConfirmed();
+    }
+
+    /**
+     * Gets users not previously involved (as primary traveler, companion, or observer) in a trip.
+     */
+    public static TripUsers getAddedUsers(MonitoredTrip monitoredTrip, MonitoredTrip originalTrip) {
+        RelatedUser addedCompanion = null;
+        if (monitoredTrip.hasConfirmedCompanion() && (
+            originalTrip == null ||
+            originalTrip.companion == null ||
+            !originalTrip.companion.email.equals(monitoredTrip.companion.email)
+        )) {
+            // Include the companion if creating trip or setting companion for the first time,
+            // or setting a different companion.
+            addedCompanion = monitoredTrip.companion;
+        }
+
+        MobilityProfileLite addedPrimaryTraveler = null;
+        if (monitoredTrip.primary != null && (
+            originalTrip == null ||
+            originalTrip.primary == null ||
+            !originalTrip.primary.userId.equals(monitoredTrip.primary.userId)
+        )) {
+            // Include the primary traveler if creating trip or setting primary traveler for the first time,
+            // or setting a different primary traveler.
+            addedPrimaryTraveler = monitoredTrip.primary;
+        }
+
+        List<RelatedUser> addedObservers = new ArrayList<>();
+        if (monitoredTrip.observers != null) {
+            List<RelatedUser> confirmedObservers = monitoredTrip.observers.stream()
+                .filter(Objects::nonNull)
+                .filter(RelatedUser::isConfirmed)
+                .collect(Collectors.toList());
+            if (originalTrip == null || originalTrip.observers == null) {
+                // Include all observers if creating trip or setting observers for the first time.
+                addedObservers.addAll(confirmedObservers);
+            } else {
+                // If observers have been set before, include observers not previously present.
+                Set<String> existingObserverEmails = originalTrip.observers.stream()
+                    .map(obs -> obs.email)
+                    .collect(Collectors.toSet());
+                confirmedObservers.forEach(obs -> {
+                    if (!existingObserverEmails.contains(obs.email)) {
+                        addedObservers.add(obs);
+                    }
+                });
+            }
+        }
+
+        return new TripUsers(addedPrimaryTraveler, addedCompanion, addedObservers);
+    }
+
+    public static class TripUsers {
+        public final RelatedUser companion;
+        public final List<RelatedUser> observers;
+        public final MobilityProfileLite primary;
+
+        public TripUsers(MobilityProfileLite primary, RelatedUser companion, List<RelatedUser> observers) {
+            this.primary = primary;
+            this.companion = companion;
+            this.observers = observers;
+        }
     }
 }
diff --git a/src/main/java/org/opentripplanner/middleware/models/RelatedUser.java b/src/main/java/org/opentripplanner/middleware/models/RelatedUser.java
index 920e94eda..25b518b56 100644
--- a/src/main/java/org/opentripplanner/middleware/models/RelatedUser.java
+++ b/src/main/java/org/opentripplanner/middleware/models/RelatedUser.java
@@ -1,5 +1,8 @@
 package org.opentripplanner.middleware.models;
 
+import com.fasterxml.jackson.annotation.JsonIgnore;
+import org.bson.codecs.pojo.annotations.BsonIgnore;
+
 /** A related user is a companion or observer requested by a dependent. */
 public class RelatedUser {
     public enum RelatedUserStatus {
@@ -15,6 +18,10 @@ public RelatedUser() {
         // Required for JSON deserialization.
     }
 
+    public RelatedUser(String email, RelatedUserStatus status) {
+        this(email, status, null);
+    }
+
     public RelatedUser(String email, RelatedUserStatus status, String nickname) {
         this.email = email;
         this.status = status;
@@ -25,5 +32,11 @@ public RelatedUser(String email, RelatedUserStatus status, String nickname, Stri
         this (email, status, nickname);
         this.acceptKey = acceptKey;
     }
+
+    @JsonIgnore
+    @BsonIgnore
+    public boolean isConfirmed() {
+        return status == RelatedUserStatus.CONFIRMED;
+    }
 }
 
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 d8c44769f..d8fbb962c 100644
--- a/src/main/java/org/opentripplanner/middleware/tripmonitor/jobs/CheckMonitoredTrip.java
+++ b/src/main/java/org/opentripplanner/middleware/tripmonitor/jobs/CheckMonitoredTrip.java
@@ -28,6 +28,7 @@
 import java.time.LocalDate;
 import java.time.ZoneId;
 import java.time.ZonedDateTime;
+import java.time.temporal.ChronoUnit;
 import java.util.ArrayList;
 import java.util.Collections;
 import java.util.Date;
@@ -59,8 +60,6 @@ public class CheckMonitoredTrip implements Runnable {
 
     public static final String ACCOUNT_PATH = "/#/account";
 
-    private final String TRIPS_PATH = ACCOUNT_PATH + "/trips";
-
     public static final String SETTINGS_PATH = ACCOUNT_PATH + "/settings";
 
     public final MonitoredTrip trip;
@@ -529,21 +528,15 @@ private void sendNotifications() {
         String tripNameOrReminder = hasInitialReminder ? initialReminderNotification.body : trip.tripName;
 
         Locale locale = getOtpUserLocale();
-        String tripLinkLabel = Message.TRIP_LINK_TEXT.get(locale);
-        String tripUrl = getTripUrl();
         // A HashMap is needed instead of a Map for template data to be serialized to the template renderer.
-        Map<String, Object> templateData = new HashMap<>(Map.of(
+        Map<String, Object> templateData = new HashMap<>();
+        templateData.putAll(Map.of(
             "emailGreeting", Message.TRIP_EMAIL_GREETING.get(locale),
             "tripNameOrReminder", tripNameOrReminder,
-            "tripLinkLabelAndUrl", label(tripLinkLabel, tripUrl, locale),
-            "tripLinkAnchorLabel", tripLinkLabel,
-            "tripUrl", tripUrl,
-            "emailFooter", String.format(Message.TRIP_EMAIL_FOOTER.get(locale), OTP_UI_NAME),
-            "manageLinkText", Message.TRIP_EMAIL_MANAGE_NOTIFICATIONS.get(locale),
-            "manageLinkUrl", String.format("%s%s", OTP_UI_URL, SETTINGS_PATH),
             "notifications", new ArrayList<>(notifications),
             "smsFooter", Message.SMS_STOP_NOTIFICATIONS.get(locale)
         ));
+        templateData.putAll(NotificationUtils.getTripNotificationFields(trip, locale));
         if (hasInitialReminder) {
             templateData.put("initialReminder", initialReminderNotification);
         }
@@ -588,9 +581,7 @@ private boolean sendPush(OtpUser otpUser, Map<String, Object> data) {
      */
     private boolean sendEmail(OtpUser otpUser, Map<String, Object> data) {
         Locale locale = getOtpUserLocale();
-        String subject = trip.tripName != null
-            ? String.format(Message.TRIP_EMAIL_SUBJECT.get(locale), trip.tripName)
-            : String.format(Message.TRIP_EMAIL_SUBJECT_FOR_USER.get(locale), otpUser.email);
+        String subject = NotificationUtils.getTripEmailSubject(otpUser, locale, trip);
         return NotificationUtils.sendEmail(
             otpUser,
             subject,
@@ -670,6 +661,18 @@ public boolean shouldSkipMonitoredTripCheck(boolean persist) throws Exception {
             return true;
         }
 
+        // For trips that are snoozed, see if they should be unsnoozed first.
+        if (trip.snoozed) {
+            if (shouldUnsnoozeTrip()) {
+                // Clear previous matching itinerary as we want to start afresh.
+                // The snoozed state will be updated later in the process.
+                previousMatchingItinerary = null;
+            } else {
+                LOG.info("Skipping: Trip is snoozed.");
+                return true;
+            }
+        }
+
         if (isPrevMatchingItineraryNotConcluded()) {
             // Skip checking the trip the rest of the time that it is active if the trip was deemed not possible for the
             // next possible time during a previous query to find candidate itinerary matches.
@@ -678,12 +681,6 @@ public boolean shouldSkipMonitoredTripCheck(boolean persist) throws Exception {
                 return true;
             }
 
-            // skip checking the trip if it has been snoozed
-            if (trip.snoozed) {
-                LOG.info("Skipping: Trip is snoozed.");
-                return true;
-            }
-
             matchingItinerary = previousMatchingItinerary;
             targetZonedDateTime = DateTimeUtils.makeOtpZonedDateTime(previousJourneyState.targetDate, trip.tripTime);
         } else {
@@ -926,7 +923,24 @@ private Locale getOtpUserLocale() {
         return I18nUtils.getOtpUserLocale(getOtpUser());
     }
 
-    private String getTripUrl() {
-        return String.format("%s%s/%s", OTP_UI_URL, TRIPS_PATH, trip.id);
+    /**
+     * Whether a trip should be unsnoozed and monitoring should resume.
+     * @return true if the current time is after the calendar day (on or after midnight)
+     * after the matching trip start day, false otherwise.
+     */
+    public boolean shouldUnsnoozeTrip() {
+        ZoneId otpZoneId = DateTimeUtils.getOtpZoneId();
+        var midnightAfterLastChecked = ZonedDateTime
+            .ofInstant(
+                Instant.ofEpochMilli(previousJourneyState.lastCheckedEpochMillis).plus(1, ChronoUnit.DAYS),
+                otpZoneId
+            )
+            .withHour(0)
+            .withMinute(0)
+            .withSecond(0);
+
+        ZonedDateTime now = DateTimeUtils.nowAsZonedDateTime(otpZoneId);
+        // Include equal or after midnight as true.
+        return !now.isBefore(midnightAfterLastChecked);
     }
 }
diff --git a/src/main/java/org/opentripplanner/middleware/triptracker/TravelerLocator.java b/src/main/java/org/opentripplanner/middleware/triptracker/TravelerLocator.java
index e444fbe62..5c7e5da32 100644
--- a/src/main/java/org/opentripplanner/middleware/triptracker/TravelerLocator.java
+++ b/src/main/java/org/opentripplanner/middleware/triptracker/TravelerLocator.java
@@ -4,6 +4,7 @@
 import org.opentripplanner.middleware.otp.response.Leg;
 import org.opentripplanner.middleware.otp.response.Place;
 import org.opentripplanner.middleware.otp.response.Step;
+import org.opentripplanner.middleware.triptracker.instruction.ContinueInstruction;
 import org.opentripplanner.middleware.triptracker.instruction.DeviatedInstruction;
 import org.opentripplanner.middleware.triptracker.instruction.GetOffHereTransitInstruction;
 import org.opentripplanner.middleware.triptracker.instruction.GetOffNextStopTransitInstruction;
@@ -27,6 +28,7 @@
 import java.util.Map;
 import java.util.Optional;
 import java.util.stream.Collectors;
+import java.util.stream.IntStream;
 
 import static org.opentripplanner.middleware.triptracker.instruction.TripInstruction.NO_INSTRUCTION;
 import static org.opentripplanner.middleware.triptracker.instruction.TripInstruction.TRIP_INSTRUCTION_IMMEDIATE_RADIUS;
@@ -59,7 +61,7 @@ public static String getInstruction(
     ) {
         if (hasRequiredWalkLeg(travelerPosition)) {
             if (hasRequiredTripStatus(tripStatus)) {
-                TripInstruction tripInstruction = alignTravelerToTrip(travelerPosition, isStartOfTrip);
+                TripInstruction tripInstruction = alignTravelerToTrip(travelerPosition, isStartOfTrip, false);
                 if (tripInstruction != null) {
                     return tripInstruction.build();
                 }
@@ -124,7 +126,7 @@ private static TripInstruction getBackOnTrack(
         TravelerPosition travelerPosition,
         boolean isStartOfTrip
     ) {
-        TripInstruction instruction = alignTravelerToTrip(travelerPosition, isStartOfTrip);
+        TripInstruction instruction = alignTravelerToTrip(travelerPosition, isStartOfTrip, true);
         if (instruction != null && instruction.hasInstruction()) {
             return instruction;
         }
@@ -169,7 +171,8 @@ private static String getBusStopName(Leg busLeg) {
     @Nullable
     public static TripInstruction alignTravelerToTrip(
         TravelerPosition travelerPosition,
-        boolean isStartOfTrip
+        boolean isStartOfTrip,
+        boolean travelerHasDeviated
     ) {
         Locale locale = travelerPosition.locale;
 
@@ -182,16 +185,72 @@ public static TripInstruction alignTravelerToTrip(
         }
 
         Step nextStep = snapToWaypoint(travelerPosition, travelerPosition.expectedLeg.steps);
+        TripInstruction tripInstruction = null;
         if (nextStep != null && (!isPositionPastStep(travelerPosition, nextStep) || isStartOfTrip)) {
-            return new OnTrackInstruction(
+            tripInstruction = new OnTrackInstruction(
                 getDistance(travelerPosition.currentPosition, new Coordinates(nextStep)),
                 nextStep,
                 locale
             );
         }
+        return (travelerHasDeviated || (tripInstruction != null && tripInstruction.hasInstruction()))
+            ? tripInstruction
+            : getContinueInstruction(travelerPosition, nextStep, locale);
+    }
+
+    /**
+     * Traveler is on track, but no immediate instruction is available. Provide a "continue on street" reassurance
+     * instruction if the traveler is on a walk leg. This will be based on the next or previous step depending on the
+     * traveler's relative position to both.
+     */
+    private static ContinueInstruction getContinueInstruction(
+        TravelerPosition travelerPosition,
+        Step nextStep,
+        Locale locale
+    ) {
+        if (
+            Boolean.TRUE.equals(!travelerPosition.expectedLeg.transitLeg) &&
+            travelerPosition.expectedLeg.steps != null &&
+            !travelerPosition.expectedLeg.steps.isEmpty()
+        ) {
+            Step previousStep = getPreviousStep(travelerPosition.expectedLeg.steps, nextStep);
+            if (previousStep != null) {
+                boolean travelerBetweenSteps = isPointBetween(previousStep.toCoordinates(), nextStep.toCoordinates(), travelerPosition.currentPosition);
+                if (travelerBetweenSteps) {
+                    return new ContinueInstruction(previousStep, locale);
+                } else if (isWithinStepRange(travelerPosition, previousStep)) {
+                    return new ContinueInstruction(previousStep, locale);
+                } else if (isWithinStepRange(travelerPosition, nextStep)) {
+                    return new ContinueInstruction(nextStep, locale);
+                }
+            }
+        }
         return null;
     }
 
+    /**
+     * The traveler is still with the provided step range.
+     */
+    private static boolean isWithinStepRange(TravelerPosition travelerPosition, Step step) {
+        double distanceFromTravelerToStep = getDistance(travelerPosition.currentPosition, step.toCoordinates());
+        return distanceFromTravelerToStep < step.distance;
+    }
+
+    /**
+     * Get the step prior to the next step provided.
+     */
+    private static Step getPreviousStep(List<Step> steps, Step nextStep) {
+        if (steps.get(0).equals(nextStep)) {
+            return null;
+        }
+        Optional<Step> previousStep = IntStream
+            .range(0, steps.size())
+            .filter(i -> steps.get(i).equals(nextStep))
+            .mapToObj(i -> steps.get(i - 1))
+            .findFirst();
+        return previousStep.orElse(null);
+    }
+
     /**
      * Send bus notification if the first leg is a bus leg or approaching a bus leg and within the notify window.
      */
diff --git a/src/main/java/org/opentripplanner/middleware/triptracker/instruction/ContinueInstruction.java b/src/main/java/org/opentripplanner/middleware/triptracker/instruction/ContinueInstruction.java
new file mode 100644
index 000000000..d961ec6d7
--- /dev/null
+++ b/src/main/java/org/opentripplanner/middleware/triptracker/instruction/ContinueInstruction.java
@@ -0,0 +1,22 @@
+package org.opentripplanner.middleware.triptracker.instruction;
+
+import org.apache.logging.log4j.util.Strings;
+import org.opentripplanner.middleware.otp.response.Step;
+
+import java.util.Locale;
+
+public class ContinueInstruction extends SelfLegInstruction {
+    public ContinueInstruction(Step legStep, Locale locale) {
+        this.legStep = legStep;
+        this.locale = locale;
+    }
+
+    @Override
+    public String build() {
+        if (legStep != null && !Strings.isBlank(legStep.streetName)) {
+            // TODO: i18n
+            return String.format("Continue on %s", legStep.streetName);
+        }
+        return NO_INSTRUCTION;
+    }
+}
diff --git a/src/main/java/org/opentripplanner/middleware/utils/NotificationUtils.java b/src/main/java/org/opentripplanner/middleware/utils/NotificationUtils.java
index 3e378d8a8..251f39240 100644
--- a/src/main/java/org/opentripplanner/middleware/utils/NotificationUtils.java
+++ b/src/main/java/org/opentripplanner/middleware/utils/NotificationUtils.java
@@ -25,6 +25,7 @@
 import java.io.IOException;
 import java.net.URI;
 import java.net.URLEncoder;
+import java.util.HashMap;
 import java.util.List;
 import java.util.Locale;
 import java.util.Map;
@@ -32,8 +33,17 @@
 import java.util.stream.Collectors;
 
 import static java.nio.charset.StandardCharsets.UTF_8;
+import static org.opentripplanner.middleware.i18n.Message.TRIP_EMAIL_FOOTER;
+import static org.opentripplanner.middleware.i18n.Message.TRIP_EMAIL_MANAGE_NOTIFICATIONS;
+import static org.opentripplanner.middleware.i18n.Message.TRIP_EMAIL_SUBJECT;
+import static org.opentripplanner.middleware.i18n.Message.TRIP_EMAIL_SUBJECT_FOR_USER;
+import static org.opentripplanner.middleware.i18n.Message.TRIP_LINK_TEXT;
 import static org.opentripplanner.middleware.i18n.Message.TRIP_SURVEY_NOTIFICATION;
+import static org.opentripplanner.middleware.tripmonitor.jobs.CheckMonitoredTrip.ACCOUNT_PATH;
+import static org.opentripplanner.middleware.tripmonitor.jobs.CheckMonitoredTrip.SETTINGS_PATH;
 import static org.opentripplanner.middleware.utils.ConfigUtils.getConfigPropertyAsText;
+import static org.opentripplanner.middleware.utils.I18nUtils.getOtpUserLocale;
+import static org.opentripplanner.middleware.utils.I18nUtils.label;
 
 /**
  * This class contains utils for sending SMS, email, and push notifications.
@@ -56,6 +66,9 @@ public class NotificationUtils {
     private static final String PUSH_API_URL = getConfigPropertyAsText("PUSH_API_URL");
     private static final String TRIP_SURVEY_ID = getConfigPropertyAsText("TRIP_SURVEY_ID");
     private static final String TRIP_SURVEY_SUBDOMAIN = getConfigPropertyAsText("TRIP_SURVEY_SUBDOMAIN");
+    private static final String OTP_UI_NAME = ConfigUtils.getConfigPropertyAsText("OTP_UI_NAME");
+    private static final String OTP_UI_URL = ConfigUtils.getConfigPropertyAsText("OTP_UI_URL");
+    private static final String TRIPS_PATH = ACCOUNT_PATH + "/trips";
 
     /**
      * Although SMS are 160 characters long and Twilio supports sending up to 1600 characters,
@@ -466,6 +479,76 @@ public static void updatePushDevices(OtpUser otpUser) {
       	}
     }
 
+    /**
+     * Gets the localized subject line for a trip notification.
+     */
+    public static String getTripEmailSubject(OtpUser otpUser, Locale locale, MonitoredTrip trip) {
+        return trip.tripName != null
+            ? String.format(TRIP_EMAIL_SUBJECT.get(locale), trip.tripName)
+            : String.format(TRIP_EMAIL_SUBJECT_FOR_USER.get(locale), otpUser.email);
+    }
+
+    /**
+     * Replaces the sender display name with the specified user's name (fallback to the user's email).
+     */
+    public static String replaceUserNameInFromEmail(String fromEmail, OtpUser otpUser) {
+        if (Strings.isBlank(fromEmail)) return fromEmail;
+
+        int firstBracketIndex = fromEmail.indexOf('<');
+        int lastBracketIndex = fromEmail.indexOf('>');
+        // HACK: If falling back on email, replace the "@" sign so that the user's email does not override the
+        // application email in brackets.
+        String displayedName = Strings.isBlank(otpUser.name) ? otpUser.email.replace("@", " at ") : otpUser.name;
+        return String.format("%s %s", displayedName, fromEmail.substring(firstBracketIndex, lastBracketIndex + 1));
+    }
+
+    /**
+     * Sends a notification to a specified companion user.
+     */
+    public static void notifyCompanion(
+        MonitoredTrip monitoredTrip,
+        OtpUser tripCreator,
+        OtpUser companionUser,
+        org.opentripplanner.middleware.i18n.Message message
+    ) {
+        if (companionUser != null) {
+            Locale locale = getOtpUserLocale(companionUser);
+            String greeting = message.get(locale);
+
+            // A HashMap is needed instead of a Map for template data to be serialized to the template renderer.
+            Map<String, Object> templateData = new HashMap<>();
+            templateData.put("emailGreeting", String.format(greeting, tripCreator.email));
+            templateData.putAll(getTripNotificationFields(monitoredTrip, locale));
+
+            sendEmail(
+                replaceUserNameInFromEmail(FROM_EMAIL, tripCreator),
+                companionUser.email,
+                getTripEmailSubject(companionUser, locale, monitoredTrip),
+                "ShareTripText.ftl",
+                "ShareTripHtml.ftl",
+                templateData
+            );
+        }
+    }
+
+    private static String getTripUrl(MonitoredTrip trip) {
+        return String.format("%s%s/%s", OTP_UI_URL, TRIPS_PATH, trip.id);
+    }
+
+    public static Map<String, Object> getTripNotificationFields(MonitoredTrip monitoredTrip, Locale locale) {
+        String tripLinkLabel = TRIP_LINK_TEXT.get(locale);
+        String tripUrl = getTripUrl(monitoredTrip);
+
+        return Map.of(
+            "tripUrl", tripUrl,
+            "tripLinkAnchorLabel", tripLinkLabel,
+            "tripLinkLabelAndUrl", label(tripLinkLabel, tripUrl, locale),
+            "emailFooter", String.format(TRIP_EMAIL_FOOTER.get(locale), OTP_UI_NAME),
+            "manageLinkText", TRIP_EMAIL_MANAGE_NOTIFICATIONS.get(locale),
+            "manageLinkUrl", String.format("%s%s", OTP_UI_URL, SETTINGS_PATH)
+        );
+    }
+
     static class NotificationInfo {
         /** ID for tracking notifications and survey responses. */
         public final String notificationId;
diff --git a/src/main/resources/Message.properties b/src/main/resources/Message.properties
index d0b090e68..397aae44b 100644
--- a/src/main/resources/Message.properties
+++ b/src/main/resources/Message.properties
@@ -29,6 +29,9 @@ TRIP_DELAY_ON_TIME = about on time
 TRIP_DELAY_EARLY = %s early
 TRIP_DELAY_LATE = %s late
 TRIP_DELAY_MINUTES = %d minutes
+TRIP_INVITE_COMPANION = %s added you as a companion for their trip.
+TRIP_INVITE_PRIMARY_TRAVELER = %s made you the primary traveler on this trip.
+TRIP_INVITE_OBSERVER = %s added you as an observer for their trip.
 TRIP_NOT_FOUND_NOTIFICATION = Your itinerary was not found in today's trip planner results. Please check real-time conditions and plan a new trip.
 TRIP_NO_LONGER_POSSIBLE_NOTIFICATION = Your itinerary is no longer possible on any monitored day of the week. Please plan and save a new trip.
 TRIP_REMINDER_NOTIFICATION = Reminder for %s at %s.
diff --git a/src/main/resources/Message_fr.properties b/src/main/resources/Message_fr.properties
index cc147ec24..1b178923d 100644
--- a/src/main/resources/Message_fr.properties
+++ b/src/main/resources/Message_fr.properties
@@ -29,6 +29,9 @@ TRIP_DELAY_ON_TIME = 
 TRIP_DELAY_EARLY = %s en avance
 TRIP_DELAY_LATE = %s en retard
 TRIP_DELAY_MINUTES = %d minutes
+TRIP_INVITE_COMPANION = %s vous a ajouté comme accompagnateur·trice pour un trajet.
+TRIP_INVITE_PRIMARY_TRAVELER = %s vous a fait le voyageur principal sur ce trajet.
+TRIP_INVITE_OBSERVER = %s vous a ajouté comme observateur·trice pour un trajet.
 TRIP_NOT_FOUND_NOTIFICATION = Votre trajet est introuvable aujourd'hui. Veuillez vérifier les conditions en temps-réel et recherchez un nouveau trajet.
 TRIP_NO_LONGER_POSSIBLE_NOTIFICATION = Votre trajet n'est plus possible dans aucun jour de suivi de la semaine. Veuillez rechercher et enregistrer un nouveau trajet.
 TRIP_REMINDER_NOTIFICATION = Rappel pour %s à %s.
diff --git a/src/main/resources/templates/ShareTripHtml.ftl b/src/main/resources/templates/ShareTripHtml.ftl
new file mode 100644
index 000000000..999ceef8b
--- /dev/null
+++ b/src/main/resources/templates/ShareTripHtml.ftl
@@ -0,0 +1,15 @@
+<#ftl auto_esc=false>
+<#include "OtpUserContainer.ftl">
+
+<#--
+    This is a template for an HTML email that gets sent when a dependent user is requesting a trusted companion.
+-->
+
+<#macro EmailMain>
+    <div>
+        <h1>${emailGreeting}</h1>
+        <p><a href="${tripUrl}">${tripLinkAnchorLabel}</a></p>
+    </div>
+</#macro>
+
+<@HtmlEmail/>
\ No newline at end of file
diff --git a/src/main/resources/templates/ShareTripText.ftl b/src/main/resources/templates/ShareTripText.ftl
new file mode 100644
index 000000000..c87ed5a0c
--- /dev/null
+++ b/src/main/resources/templates/ShareTripText.ftl
@@ -0,0 +1,11 @@
+<#--
+    This is a template for a text email that gets sent when a dependent requests a trusted companion.
+
+    Note: in plain text emails, all whitespace is preserved,
+    so the indentation of the notification content is intentionally not aligned
+    with the indentation of the macros.
+
+-->
+${emailGreeting}
+
+${tripLinkLabelAndUrl}
\ No newline at end of file
diff --git a/src/test/java/org/opentripplanner/middleware/controllers/api/OtpUserControllerTest.java b/src/test/java/org/opentripplanner/middleware/controllers/api/OtpUserControllerTest.java
index a1d9f0c9e..758885c28 100644
--- a/src/test/java/org/opentripplanner/middleware/controllers/api/OtpUserControllerTest.java
+++ b/src/test/java/org/opentripplanner/middleware/controllers/api/OtpUserControllerTest.java
@@ -212,7 +212,7 @@ void canAcceptDependentRequest() {
         relatedUsers
             .stream()
             .filter(user -> user.email.equals(relatedUserOne.email))
-            .forEach(user -> assertEquals(RelatedUser.RelatedUserStatus.CONFIRMED, user.status));
+            .forEach(user -> assertTrue(user.isConfirmed()));
     }
 
     @Test
diff --git a/src/test/java/org/opentripplanner/middleware/controllers/api/TrackedTripControllerTest.java b/src/test/java/org/opentripplanner/middleware/controllers/api/TrackedTripControllerTest.java
index 89def54b4..9124556f7 100644
--- a/src/test/java/org/opentripplanner/middleware/controllers/api/TrackedTripControllerTest.java
+++ b/src/test/java/org/opentripplanner/middleware/controllers/api/TrackedTripControllerTest.java
@@ -16,6 +16,7 @@
 import org.opentripplanner.middleware.models.TrackedJourney;
 import org.opentripplanner.middleware.otp.response.Itinerary;
 import org.opentripplanner.middleware.otp.response.Leg;
+import org.opentripplanner.middleware.otp.response.Step;
 import org.opentripplanner.middleware.persistence.Persistence;
 import org.opentripplanner.middleware.testutils.ApiTestUtils;
 import org.opentripplanner.middleware.testutils.CommonTestUtils;
@@ -27,6 +28,10 @@
 import org.opentripplanner.middleware.triptracker.TrackingLocation;
 import org.opentripplanner.middleware.triptracker.TripStatus;
 import org.opentripplanner.middleware.triptracker.TripTrackingData;
+import org.opentripplanner.middleware.triptracker.instruction.ContinueInstruction;
+import org.opentripplanner.middleware.triptracker.instruction.DeviatedInstruction;
+import org.opentripplanner.middleware.triptracker.instruction.OnTrackInstruction;
+import org.opentripplanner.middleware.triptracker.instruction.WaitForTransitInstruction;
 import org.opentripplanner.middleware.triptracker.payload.EndTrackingPayload;
 import org.opentripplanner.middleware.triptracker.payload.ForceEndTrackingPayload;
 import org.opentripplanner.middleware.triptracker.payload.StartTrackingPayload;
@@ -39,10 +44,12 @@
 import org.opentripplanner.middleware.utils.HttpResponseValues;
 import org.opentripplanner.middleware.utils.JsonUtils;
 
+import java.time.Duration;
 import java.time.Instant;
 import java.util.Date;
 import java.util.HashMap;
 import java.util.List;
+import java.util.Locale;
 import java.util.stream.Stream;
 
 import static org.junit.jupiter.api.Assertions.assertEquals;
@@ -294,88 +301,105 @@ private static Stream<Arguments> createInstructionAndStatusCases() {
         final int NORTH_WEST_BEARING = 315;
         final int NORTH_EAST_BEARING = 45;
         final int WEST_BEARING = 270;
+        final Locale locale = Locale.US;
 
         Leg firstLeg = itinerary.legs.get(0);
-        Coordinates firstStepCoords = new Coordinates(firstLeg.steps.get(0));
-        Coordinates thirdStepCoords = new Coordinates(firstLeg.steps.get(2));
+        Step adairAvenueNortheastStep = firstLeg.steps.get(0);
+        Step virginiaCircleNortheastStep = firstLeg.steps.get(1);
+        Step ponceDeLeonPlaceNortheastStep = firstLeg.steps.get(2);
+        Coordinates firstStepCoords = new Coordinates(adairAvenueNortheastStep);
+        Coordinates thirdStepCoords = new Coordinates(ponceDeLeonPlaceNortheastStep);
         Coordinates destinationCoords = new Coordinates(firstLeg.to);
+        String monroeDrDestinationName = firstLeg.to.name;
 
         Leg multiItinFirstLeg = multiLegItinerary.legs.get(0);
-        Coordinates multiItinFirstLegDestCoords = new Coordinates(multiItinFirstLeg.to);
         Leg multiItinLastLeg = multiLegItinerary.legs.get(multiLegItinerary.legs.size() - 1);
+        Leg multiItinBusLeg = multiLegItinerary.legs.get(multiLegItinerary.legs.size() - 2);
+        Coordinates multiItinFirstLegDestCoords = new Coordinates(multiItinFirstLeg.to);
         Coordinates multiItinLastLegDestCoords = new Coordinates(multiItinLastLeg.to);
+        String ansleyMallPetShopDestinationName = multiItinLastLeg.to.name;
 
         return Stream.of(
             Arguments.of(
                 monitoredTrip,
                 createPoint(firstStepCoords, 1, NORTH_EAST_BEARING),
-                "IMMEDIATE: Head WEST on Adair Avenue Northeast",
+                new OnTrackInstruction(1, adairAvenueNortheastStep, locale).build(),
                 TripStatus.ON_SCHEDULE,
                 "Coords near first step should produce relevant instruction"
             ),
             Arguments.of(
                 monitoredTrip,
                 createPoint(firstStepCoords, 4, NORTH_EAST_BEARING),
-                "UPCOMING: Head WEST on Adair Avenue Northeast",
+                new OnTrackInstruction(4, adairAvenueNortheastStep, locale).build(),
                 TripStatus.DEVIATED,
                 "Coords deviated but near first step should produce relevant instruction"
             ),
             Arguments.of(
                 monitoredTrip,
                 createPoint(firstStepCoords, 30, NORTH_EAST_BEARING),
-                "Head to Adair Avenue Northeast",
+                new DeviatedInstruction(adairAvenueNortheastStep.streetName, locale).build(),
                 TripStatus.DEVIATED,
                 "Deviated coords near first step should produce instruction to head to first step #1"
             ),
             Arguments.of(
                 monitoredTrip,
                 createPoint(firstStepCoords, 15, NORTH_WEST_BEARING),
-                "Head to Adair Avenue Northeast",
+                new DeviatedInstruction(adairAvenueNortheastStep.streetName, locale).build(),
                 TripStatus.DEVIATED,
                 "Deviated coords near first step should produce instruction to head to first step #2"
             ),
             Arguments.of(
                 monitoredTrip,
                 createPoint(firstStepCoords, 20, WEST_BEARING),
-                NO_INSTRUCTION,
+                new ContinueInstruction(adairAvenueNortheastStep, locale).build(),
                 TripStatus.ON_SCHEDULE,
-                "Coords along a step should produce no instruction"
+                "Coords along a step should produce a continue on street instruction"
             ),
             Arguments.of(
                 monitoredTrip,
                 thirdStepCoords,
-                "IMMEDIATE: LEFT on Ponce de Leon Place Northeast",
+                new OnTrackInstruction(0, ponceDeLeonPlaceNortheastStep, locale).build(),
                 TripStatus.AHEAD_OF_SCHEDULE,
                 "Coords near a not-first step should produce relevant instruction"
             ),
             Arguments.of(
                 monitoredTrip,
                 createPoint(thirdStepCoords, 30, NORTH_WEST_BEARING),
-                "Head to Ponce de Leon Place Northeast",
+                new DeviatedInstruction(ponceDeLeonPlaceNortheastStep.streetName, locale).build(),
                 TripStatus.DEVIATED,
                 "Deviated coords near a not-first step should produce instruction to head to step"
             ),
             Arguments.of(
                 monitoredTrip,
                 createPoint(destinationCoords, 1, NORTH_WEST_BEARING),
-                "ARRIVED: Monroe Dr NE at Cooledge Ave NE",
+                new OnTrackInstruction(2, monroeDrDestinationName, locale).build(),
                 TripStatus.COMPLETED,
                 "Instructions for destination coordinate"
             ),
             Arguments.of(
                 multiLegMonitoredTrip,
                 createPoint(multiItinFirstLegDestCoords, 1.5, WEST_BEARING),
-                // Time is in US Pacific time zone (instead of US Eastern) by configuration for other E2E tests.
-                "Wait 6 minutes for your bus, route 27, scheduled at 9:18 AM, on time",
+                new WaitForTransitInstruction(
+                    multiItinBusLeg,
+                    multiItinBusLeg.getScheduledStartTime().toInstant().minus(Duration.ofMinutes(6)),
+                    locale)
+                    .build(),
                 TripStatus.AHEAD_OF_SCHEDULE,
                 "Arriving ahead of schedule to a bus stop at the end of first leg."
             ),
             Arguments.of(
                 multiLegMonitoredTrip,
                 createPoint(multiItinLastLegDestCoords, 1, NORTH_WEST_BEARING),
-                "ARRIVED: Ansley Mall Pet Shop",
+                new OnTrackInstruction(1, ansleyMallPetShopDestinationName, locale).build(),
                 TripStatus.COMPLETED,
                 "Instructions for destination coordinate of multi-leg trip"
+            ),
+            Arguments.of(
+                monitoredTrip,
+                createPoint(thirdStepCoords, 1000, NORTH_WEST_BEARING),
+                NO_INSTRUCTION,
+                TripStatus.DEVIATED,
+                "Deviated significantly from nearest step should produce no instruction"
             )
         );
     }
diff --git a/src/test/java/org/opentripplanner/middleware/models/MonitoredTripTest.java b/src/test/java/org/opentripplanner/middleware/models/MonitoredTripTest.java
index dd531e8fa..a58adec69 100644
--- a/src/test/java/org/opentripplanner/middleware/models/MonitoredTripTest.java
+++ b/src/test/java/org/opentripplanner/middleware/models/MonitoredTripTest.java
@@ -10,11 +10,14 @@
 import org.opentripplanner.middleware.otp.response.Leg;
 import org.opentripplanner.middleware.otp.response.Place;
 
+import java.util.ArrayList;
 import java.util.List;
 import java.util.stream.Collectors;
 import java.util.stream.Stream;
 
 import static org.junit.jupiter.api.Assertions.assertEquals;
+import static org.opentripplanner.middleware.models.RelatedUser.RelatedUserStatus.CONFIRMED;
+import static org.opentripplanner.middleware.models.RelatedUser.RelatedUserStatus.PENDING;
 
 class MonitoredTripTest {
     @Test
@@ -70,4 +73,81 @@ private static Stream<Arguments> createHasCompanionCases() {
             Arguments.of(unconfirmedCompanion, false)
         );
     }
+
+    @ParameterizedTest
+    @MethodSource("createGetAddedUsersCases")
+    void canGetAddedUsers(MonitoredTrip.TripUsers originalUsers, MonitoredTrip.TripUsers finalUsers, MonitoredTrip.TripUsers expected) {
+        MonitoredTrip originalTrip = new MonitoredTrip();
+        originalTrip.primary = originalUsers.primary;
+        originalTrip.companion = originalUsers.companion;
+        originalTrip.observers = originalUsers.observers;
+
+        MonitoredTrip finalTrip = new MonitoredTrip();
+        finalTrip.primary = finalUsers.primary;
+        finalTrip.companion = finalUsers.companion;
+        finalTrip.observers = finalUsers.observers;
+
+        MonitoredTrip.TripUsers tripUsers = MonitoredTrip.getAddedUsers(finalTrip, originalTrip);
+
+        assertEquals(expected.primary != null, tripUsers.primary != null);
+        if (expected.primary != null && tripUsers.primary != null) {
+            assertEquals(expected.primary.userId, tripUsers.primary.userId);
+        }
+        assertEquals(expected.companion != null, tripUsers.companion != null);
+        if (expected.companion != null && tripUsers.companion != null) {
+            assertEquals(expected.companion.email, tripUsers.companion.email);
+        }
+        assertEquals(expected.observers, tripUsers.observers);
+    }
+
+    private static Stream<Arguments> createGetAddedUsersCases() {
+        MobilityProfileLite primary = new MobilityProfileLite();
+        primary.userId = "primary-user-id";
+
+        MobilityProfileLite newPrimary = new MobilityProfileLite();
+        newPrimary.userId = "new-primary-user-id";
+
+        RelatedUser companion = new RelatedUser("companion@example.com", CONFIRMED);
+        RelatedUser newCompanion = new RelatedUser("new-companion@example.com", CONFIRMED);
+        RelatedUser unconfirmedCompanion = new RelatedUser("unconfirmed-companion@example.com", PENDING);
+
+        RelatedUser observer1 = new RelatedUser("observer1@example.com", CONFIRMED);
+        RelatedUser observer2 = new RelatedUser("observer2@example.com", CONFIRMED);
+        RelatedUser observer3 = new RelatedUser("observer3@example.com", CONFIRMED);
+
+        List<RelatedUser> observers = List.of(observer1, observer2);
+
+        return Stream.of(
+            // If the final trip has the same users as the original one, no one has been added.
+            Arguments.of(
+                new MonitoredTrip.TripUsers(primary, companion, observers),
+                new MonitoredTrip.TripUsers(primary, companion, observers),
+                new MonitoredTrip.TripUsers(null, null, new ArrayList<>())
+            ),
+            // If the final trip drops original users without adding new ones, no one has been added.
+            Arguments.of(
+                new MonitoredTrip.TripUsers(primary, companion, observers),
+                new MonitoredTrip.TripUsers(null, null, List.of()),
+                new MonitoredTrip.TripUsers(null, null, new ArrayList<>())
+            ),
+            // If the original trip did not include users, users in the final trip have been added.
+            Arguments.of(
+                new MonitoredTrip.TripUsers(null, null, List.of()),
+                new MonitoredTrip.TripUsers(primary, companion, observers),
+                new MonitoredTrip.TripUsers(primary, companion, observers)
+            ),
+            // If users have been modified, the modified users should appear in added users.
+            Arguments.of(
+                new MonitoredTrip.TripUsers(primary, companion, observers),
+                new MonitoredTrip.TripUsers(newPrimary, newCompanion, List.of(observer1, observer3)),
+                new MonitoredTrip.TripUsers(newPrimary, newCompanion, List.of(observer3))
+            ),
+            // If users have been modified, unconfirmed users should not be added.
+            Arguments.of(
+                new MonitoredTrip.TripUsers(primary, companion, observers),
+                new MonitoredTrip.TripUsers(newPrimary, unconfirmedCompanion, List.of(observer1, unconfirmedCompanion)),
+                new MonitoredTrip.TripUsers(newPrimary, null, List.of())
+            )
+        );
+    }
 }
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 9bc9a3eb6..80d90ff00 100644
--- a/src/test/java/org/opentripplanner/middleware/tripmonitor/jobs/CheckMonitoredTripTest.java
+++ b/src/test/java/org/opentripplanner/middleware/tripmonitor/jobs/CheckMonitoredTripTest.java
@@ -746,4 +746,65 @@ private void assertCheckMonitoredTrip(
         assertEquals(expectedAttempts, monitoredTrip.attemptsToGetMatchingItinerary);
         assertEquals(expectedTripStatus, monitoredTrip.journeyState.tripStatus);
     }
+
+    @ParameterizedTest
+    @MethodSource("createCanUnsnoozeTripCases")
+    void canUnsnoozeTrip(ZonedDateTime lastCheckedTime, ZonedDateTime clockTime, boolean shouldUnsnooze) throws Exception {
+        MonitoredTrip monitoredTrip = PersistenceTestUtils.createMonitoredTrip(
+            user.id,
+            OtpTestUtils.OTP2_DISPATCHER_PLAN_RESPONSE.clone(),
+            false,
+            OtpTestUtils.createDefaultJourneyState()
+        );
+        monitoredTrip.id = UUID.randomUUID().toString();
+        // Mark trip as snoozed
+        monitoredTrip.snoozed = true;
+        // Set monitored days to Tuesday only.
+        monitoredTrip.monday = false;
+        monitoredTrip.tuesday = true;
+
+        Persistence.monitoredTrips.create(monitoredTrip);
+
+        // Mock the current time
+        DateTimeUtils.useFixedClockAt(clockTime);
+
+        // After snoozed trip is over, trip checks on that trip should not be skipped
+        CheckMonitoredTrip check = new CheckMonitoredTrip(monitoredTrip, this::mockOtpPlanResponse);
+
+        // Add artifacts of prior monitoring (e.g. monitoring was active until a few minutes before trip snooze)
+        JourneyState journeyState = monitoredTrip.journeyState;
+        journeyState.targetDate = "2020-06-09";
+        journeyState.tripStatus = TripStatus.TRIP_UPCOMING;
+        // Set last-checked-time
+        journeyState.lastCheckedEpochMillis = lastCheckedTime.toInstant().toEpochMilli();
+        journeyState.matchingItinerary = monitoredTrip.itinerary;
+        check.previousJourneyState = journeyState;
+        check.previousMatchingItinerary = monitoredTrip.itinerary;
+
+        assertEquals(shouldUnsnooze, check.shouldUnsnoozeTrip());
+        check.shouldSkipMonitoredTripCheck();
+
+        MonitoredTrip modifiedTrip = Persistence.monitoredTrips.getById(monitoredTrip.id);
+        assertEquals(!shouldUnsnooze, modifiedTrip.snoozed);
+
+        // Clear the created trip.
+        PersistenceTestUtils.deleteMonitoredTrip(modifiedTrip);
+    }
+
+    private static Stream<Arguments> createCanUnsnoozeTripCases() {
+        // (Trips for these tests start on Tuesday, June 9, 2020 at 8:40am and ends at 8:58am.)
+        ZonedDateTime tuesday = noonMonday8June2020.withDayOfMonth(9).withHour(0).withMinute(0).withSecond(0);
+        ZonedDateTime wednesday = tuesday.withDayOfMonth(10);
+
+        return Stream.of(
+            // Trip snoozed at 8:00am on Tuesday, June 9, 2020, should remain snoozed right after trip ends at 9:00am.
+            Arguments.of(tuesday.withHour(8), tuesday.withHour(9), false),
+            // Trip snoozed at 8:00am on Tuesday, June 9, 2020, should unsnooze at 12:00am (midnight) on
+            // Wednesday, June 10, 2020, but it is too early for the trip to be analyzed again.
+            Arguments.of(tuesday.withHour(8), wednesday, true),
+            // Trip snoozed on Monday, June 8, 2020 (a day before the trip starts), should unsnooze at 12:00am (midnight)
+            // on Tuesday, June 9, 2020.
+            Arguments.of(noonMonday8June2020, tuesday, true)
+        );
+    }
 }
diff --git a/src/test/java/org/opentripplanner/middleware/triptracker/ManageLegTraversalTest.java b/src/test/java/org/opentripplanner/middleware/triptracker/ManageLegTraversalTest.java
index ea6d6abc6..c7b546ed5 100644
--- a/src/test/java/org/opentripplanner/middleware/triptracker/ManageLegTraversalTest.java
+++ b/src/test/java/org/opentripplanner/middleware/triptracker/ManageLegTraversalTest.java
@@ -15,6 +15,7 @@
 import org.opentripplanner.middleware.otp.response.Place;
 import org.opentripplanner.middleware.otp.response.Step;
 import org.opentripplanner.middleware.testutils.CommonTestUtils;
+import org.opentripplanner.middleware.triptracker.instruction.ContinueInstruction;
 import org.opentripplanner.middleware.triptracker.instruction.DeviatedInstruction;
 import org.opentripplanner.middleware.triptracker.instruction.OnTrackInstruction;
 import org.opentripplanner.middleware.utils.ConfigUtils;
@@ -50,6 +51,7 @@ public class ManageLegTraversalTest {
     private static Itinerary midtownToAnsleyItinerary;
     private static List<Place> midtownToAnsleyIntermediateStops;
     private static Itinerary firstLegBusTransit;
+    private static Itinerary baptistChurchToEastCroganStreetIntinerary;
 
     private static final Locale locale = Locale.US;
 
@@ -78,6 +80,10 @@ public static void setUp() throws IOException {
             CommonTestUtils.getTestResourceAsString("controllers/api/first-leg-transit.json"),
             Itinerary.class
         );
+        baptistChurchToEastCroganStreetIntinerary = JsonUtils.getPOJOFromJSON(
+            CommonTestUtils.getTestResourceAsString("controllers/api/baptist-church-to-east-crogan-street.json"),
+            Itinerary.class
+        );
         // Hold on to the original list of intermediate stops (some tests will overwrite it)
         midtownToAnsleyIntermediateStops = midtownToAnsleyItinerary.legs.get(1).intermediateStops;
     }
@@ -208,6 +214,11 @@ private static Stream<Arguments> createTurnByTurnTrace() {
         Coordinates busStopCoords = new Coordinates(firstBusLeg.from);
         String busStopName = firstBusLeg.from.name;
 
+        Leg toEastCroganFirstLeg = baptistChurchToEastCroganStreetIntinerary.legs.get(0);
+        Step southClaytonSt = toEastCroganFirstLeg.steps.get(1);
+        Step eastCroganSt = toEastCroganFirstLeg.steps.get(2);
+        Coordinates pointOnSouthClaytonSt = new Coordinates(33.955561, -83.988204);
+
         return Stream.of(
             Arguments.of(
                 firstBusLeg,
@@ -270,9 +281,9 @@ private static Stream<Arguments> createTurnByTurnTrace() {
                 walkLeg,
                 new TraceData(
                     createPoint(virginiaCircleNortheastCoords, 12, SOUTH_WEST_BEARING),
-                    NO_INSTRUCTION,
+                    new ContinueInstruction(virginiaCircleNortheastStep, locale).build(),
                     false,
-                    "On track approaching second step, but not close enough for instruction."
+                    "On track approaching second step, provide continue instruction."
                 )
             ),
             Arguments.of(
@@ -336,9 +347,9 @@ private static Stream<Arguments> createTurnByTurnTrace() {
                 walkLeg,
                 new TraceData(
                     createPoint(pointAfterTurn, 0, calculateBearing(pointAfterTurn, virginiaAvenuePoint)),
-                    NO_INSTRUCTION,
+                    new ContinueInstruction(virginiaAvenueNortheastStep, locale).build(),
                     false,
-                    "After turn left on to Virginia Avenue should not produce turn instruction."
+                    "After turn left on to Virginia Avenue should provide continue instruction."
                 )
             ),
             Arguments.of(
@@ -358,6 +369,33 @@ private static Stream<Arguments> createTurnByTurnTrace() {
                     false,
                     "On destination instruction."
                 )
+            ),
+            Arguments.of(
+                toEastCroganFirstLeg,
+                new TraceData(
+                    pointOnSouthClaytonSt,
+                    new ContinueInstruction(southClaytonSt, locale).build(),
+                    false,
+                    "On track passed second step and not near to next step, provide continue instruction for second step."
+                )
+            ),
+            Arguments.of(
+                toEastCroganFirstLeg,
+                new TraceData(
+                    createPoint(pointOnSouthClaytonSt, 12, NORTH_WEST_BEARING),
+                    new ContinueInstruction(southClaytonSt, locale).build(),
+                    false,
+                    "On track a bit near to the next step, provide continue instruction for second step."
+                )
+            ),
+            Arguments.of(
+                toEastCroganFirstLeg,
+                new TraceData(
+                    createPoint(pointOnSouthClaytonSt, 72, NORTH_BEARING),
+                    new ContinueInstruction(eastCroganSt, locale).build(),
+                    false,
+                    "On track passed next step, provide continue instruction for next step."
+                )
             )
         );
     }
diff --git a/src/test/java/org/opentripplanner/middleware/utils/NotificationUtilsTest.java b/src/test/java/org/opentripplanner/middleware/utils/NotificationUtilsTest.java
index 22f6b546e..7c09326b0 100644
--- a/src/test/java/org/opentripplanner/middleware/utils/NotificationUtilsTest.java
+++ b/src/test/java/org/opentripplanner/middleware/utils/NotificationUtilsTest.java
@@ -142,4 +142,29 @@ static Stream<Arguments> createNotificationInfoCases() {
             )
         );
     }
+
+    @ParameterizedTest
+    @MethodSource("createCanReplaceUserNameInFromEmailCases")
+    void canReplaceUserNameInFromEmail(String emailAlias, OtpUser user, String expectedPrefix) {
+        String fromEmail = emailAlias != null ? String.format("RideGuide %s", emailAlias) : null;
+        String expected = fromEmail != null ? fromEmail.replace("RideGuide", expectedPrefix) : null;
+        assertEquals(expected, NotificationUtils.replaceUserNameInFromEmail(fromEmail, user));
+    }
+
+    private static Stream<Arguments> createCanReplaceUserNameInFromEmailCases() {
+        OtpUser user1 = new OtpUser();
+        user1.email = "user1@example.com";
+
+        OtpUser user2 = new OtpUser();
+        user2.email = "user2@example.com";
+        user2.name = "Joan Smith";
+
+        String emailAlias = "<rideguide@agency.example.com>";
+
+        return Stream.of(
+            Arguments.of(emailAlias, user1, "user1 at example.com"),
+            Arguments.of(null, user1, null),
+            Arguments.of(emailAlias, user2, user2.name)
+        );
+    }
 }
diff --git a/src/test/resources/org/opentripplanner/middleware/controllers/api/baptist-church-to-east-crogan-street.json b/src/test/resources/org/opentripplanner/middleware/controllers/api/baptist-church-to-east-crogan-street.json
new file mode 100644
index 000000000..0198cf5d0
--- /dev/null
+++ b/src/test/resources/org/opentripplanner/middleware/controllers/api/baptist-church-to-east-crogan-street.json
@@ -0,0 +1,107 @@
+{
+  "duration": 478,
+  "startTime": 1731606660000,
+  "endTime": 1731607138000,
+  "walkTime": 478,
+  "transitTime": 0,
+  "waitingTime": 0,
+  "walkDistance": 0,
+  "walkLimitExceeded": false,
+  "elevationLost": 0,
+  "elevationGained": 0,
+  "transfers": 0,
+  "fare": null,
+  "legs": [
+    {
+      "startTime": 1731606660000,
+      "endTime": 1731607138000,
+      "departureDelay": 0,
+      "arrivalDelay": 0,
+      "realTime": false,
+      "distance": 636.31,
+      "mode": "WALK",
+      "interlineWithPreviousLeg": false,
+      "from": {
+        "name": "First Baptist Church of Lawrenceville, Lawrenceville, GA, USA",
+        "lon": -83.9881534,
+        "lat": 33.9549491,
+        "vertexType": "NORMAL"
+      },
+      "to": {
+        "name": "49 East Crogan Street, Lawrenceville, GA, USA",
+        "lon": -83.9833418,
+        "lat": 33.9565218,
+        "vertexType": "NORMAL"
+      },
+      "legGeometry": {
+        "points": "myfnEz|r_OG@G?A?wBLI?I@_@?{@DG?Ek@GeBCk@G?I?I?A?AK?G?E?a@?]?AAE?G?M?M?E?EGwB?EAEAGAC?A@?@Y@[?C@@H@L@@?ACAAAKAQ?U?KAKAeA?O?K?KA]?K?KAg@?IAO?KE{B",
+        "length": 62
+      },
+      "rentedBike": false,
+      "transitLeg": false,
+      "duration": 478,
+      "steps": [
+        {
+          "distance": 10.11,
+          "relativeDirection": "DEPART",
+          "streetName": "crossing over Luckie Street☆☆☆",
+          "absoluteDirection": "NORTH",
+          "stayOn": false,
+          "area": false,
+          "lon": -83.9881362,
+          "lat": 33.9549515
+        },
+        {
+          "distance": 134.71,
+          "relativeDirection": "CONTINUE",
+          "streetName": "South Clayton Street★★★",
+          "absoluteDirection": "NORTH",
+          "stayOn": false,
+          "area": false,
+          "lon": -83.9881458,
+          "lat": 33.955042
+        },
+        {
+          "distance": 88.77,
+          "relativeDirection": "RIGHT",
+          "streetName": "East Crogan Street★★★",
+          "absoluteDirection": "EAST",
+          "stayOn": true,
+          "area": false,
+          "lon": -83.9882578,
+          "lat": 33.9562495
+        },
+        {
+          "distance": 17.43,
+          "relativeDirection": "LEFT",
+          "streetName": "crossing over East Crogan Street☆☆☆",
+          "absoluteDirection": "NORTH",
+          "stayOn": true,
+          "area": false,
+          "lon": -83.9873003,
+          "lat": 33.9563302
+        },
+        {
+          "distance": 177.64,
+          "relativeDirection": "RIGHT",
+          "streetName": "East Crogan Street★★★",
+          "absoluteDirection": "EAST",
+          "stayOn": false,
+          "area": false,
+          "lon": -83.9873097,
+          "lat": 33.9564868
+        },
+        {
+          "distance": 207.65,
+          "relativeDirection": "LEFT",
+          "streetName": "East Crogan Street★★★",
+          "absoluteDirection": "EAST",
+          "stayOn": true,
+          "area": false,
+          "lon": -83.985582,
+          "lat": 33.9564082
+        }
+      ]
+    }
+  ]
+}
\ No newline at end of file