diff --git a/nodeup/pkg/model/logrotate.go b/nodeup/pkg/model/logrotate.go
index e78e50df29..53eed5fd62 100644
--- a/nodeup/pkg/model/logrotate.go
+++ b/nodeup/pkg/model/logrotate.go
@@ -113,7 +113,8 @@ func (b *LogrotateBuilder) addLogrotateService(c *fi.ModelBuilderContext) error
 }
 
 type logRotateOptions struct {
-	MaxSize string
+	MaxSize    string
+	DateFormat string
 }
 
 func (b *LogrotateBuilder) addLogRotate(c *fi.ModelBuilderContext, name, path string, options logRotateOptions) {
@@ -121,6 +122,12 @@ func (b *LogrotateBuilder) addLogRotate(c *fi.ModelBuilderContext, name, path st
 		options.MaxSize = "100M"
 	}
 
+	// CoreOS sets "dateext" options, and maxsize-based rotation will fail if
+	// the file has been previously rotated on the same calendar date.
+	if b.Distribution == distros.DistributionCoreOS {
+		options.DateFormat = "-%Y%m%d-%s"
+	}
+
 	lines := []string{
 		path + "{",
 		"  rotate 5",
@@ -129,12 +136,20 @@ func (b *LogrotateBuilder) addLogRotate(c *fi.ModelBuilderContext, name, path st
 		"  notifempty",
 		"  delaycompress",
 		"  maxsize " + options.MaxSize,
+	}
+
+	if options.DateFormat != "" {
+		lines = append(lines, "  dateformat "+options.DateFormat)
+	}
+
+	lines = append(
+		lines,
 		"  daily",
 		"  create 0644 root root",
 		"}",
-	}
+	)
 
-	contents := strings.Join(lines, "\n")
+	contents := strings.Join(lines, "\n") + "\n"
 
 	c.AddTask(&nodetasks.File{
 		Path:     "/etc/logrotate.d/" + name,