diff --git a/caddyhttp/httpserver/condition.go b/caddyhttp/httpserver/condition.go
index a45dffe0..986125c1 100644
--- a/caddyhttp/httpserver/condition.go
+++ b/caddyhttp/httpserver/condition.go
@@ -52,6 +52,7 @@ const (
 	startsWithOp    = "starts_with"
 	notStartsWithOp = "not_starts_with"
 	endsWithOp      = "ends_with"
+	notEndsWithOp   = "not_ends_with"
 	matchOp         = "match"
 	notMatchOp      = "not_match"
 )
@@ -71,6 +72,7 @@ var ifConditions = map[string]ifCondition{
 	startsWithOp:    startsWithFunc,
 	notStartsWithOp: notStartsWithFunc,
 	endsWithOp:      endsWithFunc,
+	notEndsWithOp:   notEndsWithFunc,
 	matchOp:         matchFunc,
 	notMatchOp:      notMatchFunc,
 }
@@ -84,7 +86,7 @@ func isFunc(a, b string) bool {
 // notFunc is condition for Not operator.
 // It checks for inequality.
 func notFunc(a, b string) bool {
-	return a != b
+	return !isFunc(a, b)
 }
 
 // hasFunc is condition for Has operator.
@@ -96,7 +98,7 @@ func hasFunc(a, b string) bool {
 // notHasFunc is condition for NotHas operator.
 // It checks if b is not a substring of a.
 func notHasFunc(a, b string) bool {
-	return !strings.Contains(a, b)
+	return !hasFunc(a, b)
 }
 
 // startsWithFunc is condition for StartsWith operator.
@@ -108,7 +110,7 @@ func startsWithFunc(a, b string) bool {
 // notStartsWithFunc is condition for NotStartsWith operator.
 // It checks if b is not a prefix of a.
 func notStartsWithFunc(a, b string) bool {
-	return !strings.HasPrefix(a, b)
+	return !startsWithFunc(a, b)
 }
 
 // endsWithFunc is condition for EndsWith operator.
@@ -117,6 +119,12 @@ func endsWithFunc(a, b string) bool {
 	return strings.HasSuffix(a, b)
 }
 
+// notEndsWithFunc is condition for NotEndsWith operator.
+// It checks if b is not a suffix of a.
+func notEndsWithFunc(a, b string) bool {
+	return !endsWithFunc(a, b)
+}
+
 // matchFunc is condition for Match operator.
 // It does regexp matching of a against pattern in b
 // and returns if they match.
@@ -129,8 +137,7 @@ func matchFunc(a, b string) bool {
 // It does regexp matching of a against pattern in b
 // and returns if they do not match.
 func notMatchFunc(a, b string) bool {
-	matched, _ := regexp.MatchString(b, a)
-	return !matched
+	return !matchFunc(a, b)
 }
 
 // ifCond is statement for a IfMatcher condition.
diff --git a/caddyhttp/httpserver/condition_test.go b/caddyhttp/httpserver/condition_test.go
index 4ccac0e0..0b50450f 100644
--- a/caddyhttp/httpserver/condition_test.go
+++ b/caddyhttp/httpserver/condition_test.go
@@ -38,6 +38,9 @@ func TestConditions(t *testing.T) {
 		{"bab ends_with bb", false},
 		{"bab ends_with bab", true},
 		{"bab ends_with ab", true},
+		{"bab not_ends_with bb", true},
+		{"bab not_ends_with ab", false},
+		{"bab not_ends_with bab", false},
 		{"a match *", false},
 		{"a match a", true},
 		{"a match .*", true},
@@ -224,7 +227,7 @@ func TestSetupIfMatcher(t *testing.T) {
 		},
 		{`test {
 			if goal has go
-			if cook not_has go 
+			if cook not_has go
 		 }`, false, IfMatcher{
 			ifs: []ifCond{
 				{a: "goal", op: "has", b: "go"},
@@ -233,7 +236,7 @@ func TestSetupIfMatcher(t *testing.T) {
 		}},
 		{`test {
 			if goal has go
-			if cook not_has go 
+			if cook not_has go
 			if_op and
 		 }`, false, IfMatcher{
 			ifs: []ifCond{
@@ -243,7 +246,7 @@ func TestSetupIfMatcher(t *testing.T) {
 		}},
 		{`test {
 			if goal has go
-			if cook not_has go 
+			if cook not_has go
 			if_op not
 		 }`, true, IfMatcher{},
 		},