diff --git a/hapi-fhir-docs/src/main/resources/ca/uhn/hapi/fhir/changelog/7_2_0/5877-exception-when-updating-token-param-with-large-value.yaml b/hapi-fhir-docs/src/main/resources/ca/uhn/hapi/fhir/changelog/7_2_0/5877-exception-when-updating-token-param-with-large-value.yaml
new file mode 100644
index 00000000000..ad6bbd02d1f
--- /dev/null
+++ b/hapi-fhir-docs/src/main/resources/ca/uhn/hapi/fhir/changelog/7_2_0/5877-exception-when-updating-token-param-with-large-value.yaml
@@ -0,0 +1,5 @@
+---
+type: fix
+issue: 5877
+title: "Previously, updating a tokenParam with a value greater than 200 characters would raise a SQLException.  
+This issue has been fixed."
diff --git a/hapi-fhir-jpaserver-model/src/main/java/ca/uhn/fhir/jpa/model/entity/ResourceIndexedSearchParamToken.java b/hapi-fhir-jpaserver-model/src/main/java/ca/uhn/fhir/jpa/model/entity/ResourceIndexedSearchParamToken.java
index 2a8ba6e8d03..9066f9f25db 100644
--- a/hapi-fhir-jpaserver-model/src/main/java/ca/uhn/fhir/jpa/model/entity/ResourceIndexedSearchParamToken.java
+++ b/hapi-fhir-jpaserver-model/src/main/java/ca/uhn/fhir/jpa/model/entity/ResourceIndexedSearchParamToken.java
@@ -36,6 +36,7 @@ import jakarta.persistence.Index;
 import jakarta.persistence.JoinColumn;
 import jakarta.persistence.ManyToOne;
 import jakarta.persistence.PrePersist;
+import jakarta.persistence.PreUpdate;
 import jakarta.persistence.SequenceGenerator;
 import jakarta.persistence.Table;
 import org.apache.commons.lang3.StringUtils;
@@ -429,6 +430,7 @@ public class ResourceIndexedSearchParamToken extends BaseResourceIndexedSearchPa
 	 * We don't truncate earlier in the flow because the index hashes MUST be calculated on the full string.
 	 */
 	@PrePersist
+	@PreUpdate
 	public void truncateFieldsForDB() {
 		mySystem = StringUtils.truncate(mySystem, MAX_LENGTH);
 		myValue = StringUtils.truncate(myValue, MAX_LENGTH);
diff --git a/hapi-fhir-jpaserver-test-r4/src/test/java/ca/uhn/fhir/jpa/dao/r4/FhirResourceDaoR4Test.java b/hapi-fhir-jpaserver-test-r4/src/test/java/ca/uhn/fhir/jpa/dao/r4/FhirResourceDaoR4Test.java
index 649359d3937..d0e33aaba8c 100644
--- a/hapi-fhir-jpaserver-test-r4/src/test/java/ca/uhn/fhir/jpa/dao/r4/FhirResourceDaoR4Test.java
+++ b/hapi-fhir-jpaserver-test-r4/src/test/java/ca/uhn/fhir/jpa/dao/r4/FhirResourceDaoR4Test.java
@@ -54,7 +54,6 @@ import ca.uhn.fhir.rest.server.exceptions.ResourceNotFoundException;
 import ca.uhn.fhir.rest.server.exceptions.ResourceVersionConflictException;
 import ca.uhn.fhir.rest.server.exceptions.UnprocessableEntityException;
 import ca.uhn.fhir.util.ClasspathUtil;
-import com.google.common.base.Charsets;
 import com.google.common.collect.Lists;
 import org.apache.commons.io.IOUtils;
 import org.apache.commons.lang3.RandomStringUtils;
@@ -83,6 +82,7 @@ import org.hl7.fhir.r4.model.CompartmentDefinition;
 import org.hl7.fhir.r4.model.ConceptMap;
 import org.hl7.fhir.r4.model.Condition;
 import org.hl7.fhir.r4.model.Consent;
+import org.hl7.fhir.r4.model.ContactPoint;
 import org.hl7.fhir.r4.model.DateTimeType;
 import org.hl7.fhir.r4.model.DateType;
 import org.hl7.fhir.r4.model.Device;
@@ -157,9 +157,11 @@ import static org.hamcrest.Matchers.equalTo;
 import static org.hamcrest.Matchers.greaterThan;
 import static org.hamcrest.Matchers.hasItem;
 import static org.hamcrest.Matchers.hasItems;
+import static org.hamcrest.Matchers.hasLength;
 import static org.hamcrest.Matchers.hasSize;
 import static org.hamcrest.Matchers.matchesPattern;
 import static org.hamcrest.Matchers.not;
+import static org.hamcrest.Matchers.startsWith;
 import static org.junit.jupiter.api.Assertions.assertEquals;
 import static org.junit.jupiter.api.Assertions.assertFalse;
 import static org.junit.jupiter.api.Assertions.assertNotEquals;
@@ -247,6 +249,42 @@ public class FhirResourceDaoR4Test extends BaseJpaR4Test {
 		return retVal;
 	}
 
+	@Test
+	public void testUpdateResource_whenTokenPropertyAssignedTooLargeValue_willTruncateLargeValueOnUpdate(){
+		// given
+		final String modifiedEmailPrefix = "modified";
+		final String originalEmail = RandomStringUtils.randomAlphanumeric(ResourceIndexedSearchParamToken.MAX_LENGTH) + "@acme.corp";
+		final String modifiedEmail = modifiedEmailPrefix + originalEmail;
+
+		// when
+		Patient pt1 = new Patient();
+		pt1.setActive(true);
+		pt1.addName().setFamily("FAM");
+		pt1.addTelecom().setSystem(ContactPoint.ContactPointSystem.EMAIL).setValue(originalEmail);
+
+		myPatientDao.create(pt1).getId().toUnqualifiedVersionless();
+
+		pt1.getTelecomFirstRep().setValue(modifiedEmail);
+
+		IIdType id1 = myPatientDao.update(pt1).getId().toUnqualifiedVersionless();
+
+		// then
+		runInTransaction(() -> {
+			List<String> paramValues = myResourceIndexedSearchParamTokenDao
+				.findAll()
+				.stream()
+				.filter(t -> defaultString(t.getSystem()).equals("email"))
+				.map(t -> t.getValue())
+				.collect(Collectors.toList());
+
+			assertThat(paramValues, hasSize(2));
+
+			for (String tokenValue : paramValues) {
+				assertThat(tokenValue, startsWith(modifiedEmailPrefix));
+				assertThat(tokenValue, hasLength(ResourceIndexedSearchParamToken.MAX_LENGTH));
+			}
+		});
+	}
 
 	@Test
 	public void testDeletedResourcesAreReindexed() {