diff --git a/agent/utils/ssl/manual_client.go b/agent/utils/ssl/manual_client.go
index dc501e893adc..655de5524bb7 100644
--- a/agent/utils/ssl/manual_client.go
+++ b/agent/utils/ssl/manual_client.go
@@ -71,12 +71,39 @@ type Resolve struct {
 }
 
 func (c *ManualClient) GetDNSResolve(ctx context.Context, websiteSSL *model.WebsiteSSL) (map[string]Resolve, error) {
-	order, err := c.client.AuthorizeOrder(ctx, acme.DomainIDs(getWebsiteSSLDomains(websiteSSL)...))
+	var order *acme.Order
+	var err error
+
+	// Check if we have an existing valid order for this SSL
+	existingOrder, exists := Orders[websiteSSL.ID]
+	if exists && existingOrder != nil {
+		// Verify the order is still valid (not expired and still pending)
+		// If Expires is zero, order is still valid (ACME doesn't always set expiry immediately)
+		isNotExpired := existingOrder.Expires.IsZero() || existingOrder.Expires.After(time.Now())
+		if isNotExpired && (existingOrder.Status == acme.StatusPending || existingOrder.Status == acme.StatusReady) {
+			// Try to reuse the existing order
+			records, err := c.extractDNSChallenges(ctx, existingOrder)
+			if err == nil && len(records) > 0 {
+				return records, nil
+			}
+			// If extraction failed, fall through to create a new order
+		}
+		// Existing order is expired or invalid, remove it
+		delete(Orders, websiteSSL.ID)
+	}
+
+	// Create a new order
+	order, err = c.client.AuthorizeOrder(ctx, acme.DomainIDs(getWebsiteSSLDomains(websiteSSL)...))
 	if err != nil {
 		return nil, err
 	}
 	Orders[websiteSSL.ID] = order
 
+	return c.extractDNSChallenges(ctx, order)
+}
+
+// extractDNSChallenges extracts DNS-01 challenge values from an ACME order
+func (c *ManualClient) extractDNSChallenges(ctx context.Context, order *acme.Order) (map[string]Resolve, error) {
 	records := make(map[string]Resolve)
 
 	for _, authzURL := range order.AuthzURLs {
@@ -103,7 +130,14 @@ func (c *ManualClient) GetDNSResolve(ctx context.Context, websiteSSL *model.Webs
 			return nil, err
 		}
 
-		records[domain] = Resolve{
+		// Use different map key for wildcard vs non-wildcard to avoid overwriting
+		// Both use the same DNS record name (_acme-challenge.domain) but different values
+		mapKey := domain
+		if authz.Wildcard {
+			mapKey = "*." + domain
+		}
+
+		records[mapKey] = Resolve{
 			Key:   fmt.Sprintf("_acme-challenge.%s", domain),
 			Value: txtValue,
 		}
@@ -111,15 +145,15 @@ func (c *ManualClient) GetDNSResolve(ctx context.Context, websiteSSL *model.Webs
 	return records, nil
 }
 
-func queryDNSRecords(domain string) (map[string]string, error) {
+func queryDNSRecords(domain string) (map[string][]string, error) {
 	recordName := fmt.Sprintf("_acme-challenge.%s", domain)
 	txts, err := net.LookupTXT(recordName)
 	if err != nil {
 		return nil, err
 	}
-	records := make(map[string]string)
+	records := make(map[string][]string)
 	if len(txts) > 0 {
-		records[recordName] = txts[0]
+		records[recordName] = txts
 	}
 	return records, nil
 }
@@ -159,7 +193,7 @@ func (c *ManualClient) handleAuthorization(ctx context.Context, authzURL string,
 
 	for {
 		c.logger.Printf("[INFO] [%s] acme: Checking DNS record propagation.", domain)
-		var currentRecords map[string]string
+		var currentRecords map[string][]string
 		var queryErr error
 		if len(nameservers) == 0 {
 			currentRecords, queryErr = queryDNSRecords(domain)
@@ -177,16 +211,26 @@ func (c *ManualClient) handleAuthorization(ctx context.Context, authzURL string,
 			return fmt.Errorf("failed to query DNS records: %v", queryErr)
 		}
 		recordName := fmt.Sprintf("_acme-challenge.%s", domain)
-		providedRecord, exists := currentRecords[recordName]
-		if exists && providedRecord == expectedRecord {
+		providedRecords, exists := currentRecords[recordName]
+		// Check if expected record is in any of the TXT values
+		found := false
+		if exists {
+			for _, record := range providedRecords {
+				if record == expectedRecord {
+					found = true
+					break
+				}
+			}
+		}
+		if found {
 			break
 		}
 		if time.Now().After(deadline) {
-			if !exists {
+			if !exists || len(providedRecords) == 0 {
 				return fmt.Errorf("TXT record not provided for domain %s after retrying", domain)
 			}
-			c.logger.Printf("[INFO] [%s] TXT record mismatch for %s: expected %s, got %s\"", domain, domain, expectedRecord, providedRecord)
-			return fmt.Errorf("TXT record mismatch for %s: expected %s, got %s", domain, expectedRecord, providedRecord)
+			c.logger.Printf("[INFO] [%s] TXT record mismatch for %s: expected %s, got %v", domain, domain, expectedRecord, providedRecords)
+			return fmt.Errorf("TXT record mismatch for %s: expected %s, got %v", domain, expectedRecord, providedRecords)
 		}
 		time.Sleep(pollingInterval)
 	}
@@ -339,7 +383,7 @@ func handleNameserver(nameserver string) string {
 	return fmt.Sprintf("%s:53", nameserver)
 }
 
-func queryDNSRecordsWithResolver(ctx context.Context, logger *log.Logger, domain string, dnsServer string) (map[string]string, error) {
+func queryDNSRecordsWithResolver(ctx context.Context, logger *log.Logger, domain string, dnsServer string) (map[string][]string, error) {
 	recordName := fmt.Sprintf("_acme-challenge.%s", domain)
 	c := new(dns.Client)
 	c.Timeout = 10 * time.Second
@@ -367,16 +411,19 @@ func queryDNSRecordsWithResolver(ctx context.Context, logger *log.Logger, domain
 		return nil, fmt.Errorf("DNS query failed with code: %s", dns.RcodeToString[r.Rcode])
 	}
 
-	records := make(map[string]string)
+	records := make(map[string][]string)
+	var txtValues []string
 
 	for _, answer := range r.Answer {
 		if txt, ok := answer.(*dns.TXT); ok {
 			if len(txt.Txt) > 0 {
-				records[recordName] = txt.Txt[0]
-				break
+				txtValues = append(txtValues, txt.Txt[0])
 			}
 		}
 	}
+	if len(txtValues) > 0 {
+		records[recordName] = txtValues
+	}
 
 	return records, nil
 }