diff --git a/cmd/jiralert/main.go b/cmd/jiralert/main.go
index 86be130..6f8ddec 100644
--- a/cmd/jiralert/main.go
+++ b/cmd/jiralert/main.go
@@ -36,9 +36,10 @@ import (
 )
 
 const (
-	unknownReceiver = "<unknown>"
-	logFormatLogfmt = "logfmt"
-	logFormatJSON   = "json"
+	unknownReceiver             = "<unknown>"
+	logFormatLogfmt             = "logfmt"
+	logFormatJSON               = "json"
+	defaultMaxDescriptionLength = 32767 // https://jira.atlassian.com/browse/JRASERVER-64351
 )
 
 var (
@@ -48,9 +49,10 @@ var (
 	logFormat     = flag.String("log.format", logFormatLogfmt, "Log format to use ("+logFormatLogfmt+", "+logFormatJSON+")")
 	hashJiraLabel = flag.Bool("hash-jira-label", false, "if enabled: renames ALERT{...} to JIRALERT{...}; also hashes the key-value pairs inside of JIRALERT{...} in the created jira issue labels"+
 		"- this ensures that the label text does not overflow the allowed length in jira (255)")
-	updateSummary     = flag.Bool("update-summary", true, "When false, jiralert does not update the summary of the existing jira issue, even when changes are spotted.")
-	updateDescription = flag.Bool("update-description", true, "When false, jiralert does not update the description of the existing jira issue, even when changes are spotted.")
-	reopenTickets     = flag.Bool("reopen-tickets", true, "When false, jiralert does not reopen tickets.")
+	updateSummary        = flag.Bool("update-summary", true, "When false, jiralert does not update the summary of the existing jira issue, even when changes are spotted.")
+	updateDescription    = flag.Bool("update-description", true, "When false, jiralert does not update the description of the existing jira issue, even when changes are spotted.")
+	reopenTickets        = flag.Bool("reopen-tickets", true, "When false, jiralert does not reopen tickets.")
+	maxDescriptionLength = flag.Int("max-description-length", defaultMaxDescriptionLength, "Maximum length of Descriptions. Truncate to this size avoid server errors.")
 
 	// Version is the build version, set by make to latest git tag/hash via `-ldflags "-X main.Version=$(VERSION)"`.
 	Version = "<local build>"
@@ -124,7 +126,7 @@ func main() {
 			return
 		}
 
-		if retry, err := notify.NewReceiver(logger, conf, tmpl, client.Issue).Notify(&data, *hashJiraLabel, *updateSummary, *updateDescription, *reopenTickets); err != nil {
+		if retry, err := notify.NewReceiver(logger, conf, tmpl, client.Issue).Notify(&data, *hashJiraLabel, *updateSummary, *updateDescription, *reopenTickets, *maxDescriptionLength); err != nil {
 			var status int
 			if retry {
 				// Instruct Alertmanager to retry.
diff --git a/pkg/notify/notify.go b/pkg/notify/notify.go
index c4a5c46..b929e4b 100644
--- a/pkg/notify/notify.go
+++ b/pkg/notify/notify.go
@@ -61,7 +61,7 @@ func NewReceiver(logger log.Logger, c *config.ReceiverConfig, t *template.Templa
 }
 
 // Notify manages JIRA issues based on alertmanager webhook notify message.
-func (r *Receiver) Notify(data *alertmanager.Data, hashJiraLabel bool, updateSummary bool, updateDescription bool, reopenTickets bool) (bool, error) {
+func (r *Receiver) Notify(data *alertmanager.Data, hashJiraLabel bool, updateSummary bool, updateDescription bool, reopenTickets bool, maxDescriptionLength int) (bool, error) {
 	project, err := r.tmpl.Execute(r.conf.Project, data)
 	if err != nil {
 		return false, errors.Wrap(err, "generate project from template")
@@ -86,6 +86,11 @@ func (r *Receiver) Notify(data *alertmanager.Data, hashJiraLabel bool, updateSum
 		return false, errors.Wrap(err, "render issue description")
 	}
 
+	if len(issueDesc) > maxDescriptionLength {
+		level.Warn(r.logger).Log("msg", "truncating description", "original", len(issueDesc), "limit", maxDescriptionLength)
+		issueDesc = issueDesc[:maxDescriptionLength]
+	}
+
 	if issue != nil {
 
 		// Update summary if needed.
diff --git a/pkg/notify/notify_test.go b/pkg/notify/notify_test.go
index cb4b0f3..bd3d022 100644
--- a/pkg/notify/notify_test.go
+++ b/pkg/notify/notify_test.go
@@ -597,7 +597,7 @@ func TestNotify_JIRAInteraction(t *testing.T) {
 				return testNowTime
 			}
 
-			_, err := receiver.Notify(tcase.inputAlert, true, true, true, true)
+			_, err := receiver.Notify(tcase.inputAlert, true, true, true, true, 32768)
 			require.NoError(t, err)
 			require.Equal(t, tcase.expectedJiraIssues, fakeJira.issuesByKey)
 		}); !ok {