diff --git a/pkg/equality/elbv2/compare_option_for_rule_conditions.go b/pkg/equality/elbv2/compare_option_for_rule_conditions.go
index f858cfefd2..871bda03f0 100644
--- a/pkg/equality/elbv2/compare_option_for_rule_conditions.go
+++ b/pkg/equality/elbv2/compare_option_for_rule_conditions.go
@@ -17,7 +17,7 @@ func CompareOptionForRuleCondition() cmp.Option {
 		cmpopts.IgnoreUnexported(elbv2types.QueryStringConditionConfig{}),
 		cmpopts.IgnoreUnexported(elbv2types.QueryStringKeyValuePair{}),
 		cmpopts.IgnoreUnexported(elbv2types.SourceIpConditionConfig{}),
-		cmpopts.IgnoreFields(elbv2types.RuleCondition{}, "Values"),
+		cmpopts.IgnoreFields(elbv2types.RuleCondition{}, "Values", "RegexValues"),
 	}
 }
 
diff --git a/pkg/equality/elbv2/compare_option_for_rule_conditions_test.go b/pkg/equality/elbv2/compare_option_for_rule_conditions_test.go
index 8210478319..361b4de926 100644
--- a/pkg/equality/elbv2/compare_option_for_rule_conditions_test.go
+++ b/pkg/equality/elbv2/compare_option_for_rule_conditions_test.go
@@ -79,6 +79,60 @@ func Test_CompareOptionForRuleConditions(t *testing.T) {
 			},
 			expected: true,
 		},
+		{
+			name: "equal - regex path pattern with AWS-mirrored top-level RegexValues",
+			desiredRuleCondition: []types.RuleCondition{
+				{
+					Field: awssdk.String("host-header"),
+					HostHeaderConfig: &types.HostHeaderConditionConfig{
+						Values: []string{"example.com"},
+					},
+				},
+				{
+					Field: awssdk.String("path-pattern"),
+					PathPatternConfig: &types.PathPatternConditionConfig{
+						RegexValues: []string{"^/api/v1/.*"},
+					},
+				},
+			},
+			actualRuleCondition: []types.RuleCondition{
+				{
+					Field: awssdk.String("host-header"),
+					HostHeaderConfig: &types.HostHeaderConditionConfig{
+						Values: []string{"example.com"},
+					},
+				},
+				{
+					Field: awssdk.String("path-pattern"),
+					PathPatternConfig: &types.PathPatternConditionConfig{
+						RegexValues: []string{"^/api/v1/.*"},
+					},
+					RegexValues: []string{"^/api/v1/.*"},
+				},
+			},
+			expected: true,
+		},
+		{
+			name: "not equal - different regex path pattern",
+			desiredRuleCondition: []types.RuleCondition{
+				{
+					Field: awssdk.String("path-pattern"),
+					PathPatternConfig: &types.PathPatternConditionConfig{
+						RegexValues: []string{"^/api/v1/.*"},
+					},
+				},
+			},
+			actualRuleCondition: []types.RuleCondition{
+				{
+					Field: awssdk.String("path-pattern"),
+					PathPatternConfig: &types.PathPatternConditionConfig{
+						RegexValues: []string{"^/api/v2/.*"},
+					},
+					RegexValues: []string{"^/api/v2/.*"},
+				},
+			},
+			expected: false,
+		},
 	}
 
 	for _, tc := range testCase {
diff --git a/pkg/ingress/rule_optimizer.go b/pkg/ingress/rule_optimizer.go
index 6b1cbb47a1..1a67cd35e4 100644
--- a/pkg/ingress/rule_optimizer.go
+++ b/pkg/ingress/rule_optimizer.go
@@ -98,6 +98,10 @@ func isInfiniteRedirectRule(port int32, protocol elbv2model.Protocol, rule Rule)
 		case condition.Field == elbv2model.RuleConditionFieldHostHeader && condition.HostHeaderConfig != nil:
 			ruleHosts.Insert(condition.HostHeaderConfig.Values...)
 		case condition.Field == elbv2model.RuleConditionFieldPathPattern && condition.PathPatternConfig != nil:
+			// We dont check for infinite rules for regex paths
+			if len(condition.PathPatternConfig.RegexValues) > 0 {
+				return false
+			}
 			rulePaths.Insert(condition.PathPatternConfig.Values...)
 		}
 	}
@@ -146,7 +150,11 @@ func isSupersetConditions(lhsConditions []elbv2model.RuleCondition, rhsCondition
 		case condition.Field == elbv2model.RuleConditionFieldHostHeader && condition.HostHeaderConfig != nil:
 			lhsHosts.Insert(condition.HostHeaderConfig.Values...)
 		case condition.Field == elbv2model.RuleConditionFieldPathPattern && condition.PathPatternConfig != nil:
-			lhsPaths.Insert(condition.PathPatternConfig.Values...)
+			if len(condition.PathPatternConfig.RegexValues) > 0 {
+				lhsPaths.Insert(condition.PathPatternConfig.RegexValues...)
+			} else {
+				lhsPaths.Insert(condition.PathPatternConfig.Values...)
+			}
 		default:
 			// if there are any other conditions, then we treat it as not superset.
 			return false
@@ -160,7 +168,11 @@ func isSupersetConditions(lhsConditions []elbv2model.RuleCondition, rhsCondition
 		case condition.Field == elbv2model.RuleConditionFieldHostHeader && condition.HostHeaderConfig != nil:
 			rhsHosts.Insert(condition.HostHeaderConfig.Values...)
 		case condition.Field == elbv2model.RuleConditionFieldPathPattern && condition.PathPatternConfig != nil:
-			rhsPaths.Insert(condition.PathPatternConfig.Values...)
+			if len(condition.PathPatternConfig.RegexValues) > 0 {
+				rhsPaths.Insert(condition.PathPatternConfig.RegexValues...)
+			} else {
+				rhsPaths.Insert(condition.PathPatternConfig.Values...)
+			}
 		}
 	}
 
diff --git a/pkg/ingress/rule_optimizer_test.go b/pkg/ingress/rule_optimizer_test.go
index b76ba11150..46dfdac1f6 100644
--- a/pkg/ingress/rule_optimizer_test.go
+++ b/pkg/ingress/rule_optimizer_test.go
@@ -231,6 +231,886 @@ func Test_defaultRuleOptimizer_Optimize(t *testing.T) {
 				},
 			},
 		},
+		{
+			name: "catch-all regex rule should NOT overshadow specific regex rules",
+			args: args{
+				port:     443,
+				protocol: elbv2model.ProtocolHTTPS,
+				rules: []Rule{
+					{
+						Conditions: []elbv2model.RuleCondition{
+							{
+								Field: elbv2model.RuleConditionFieldHostHeader,
+								HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+									Values: []string{"a.example.com"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldPathPattern,
+								PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+									RegexValues: []string{"^/.*$"},
+								},
+							},
+						},
+						Actions: []elbv2model.Action{
+							{
+								Type: elbv2model.ActionTypeRedirect,
+								RedirectConfig: &elbv2model.RedirectActionConfig{
+									Host:       awssdk.String("default.example.com"),
+									Path:       awssdk.String("/#{path}"),
+									StatusCode: "HTTP_302",
+								},
+							},
+						},
+					},
+					{
+						Conditions: []elbv2model.RuleCondition{
+							{
+								Field: elbv2model.RuleConditionFieldHostHeader,
+								HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+									Values: []string{"a.example.com"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldPathPattern,
+								PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+									RegexValues: []string{"^/api/.*"},
+								},
+							},
+						},
+						Actions: []elbv2model.Action{
+							{
+								Type: elbv2model.ActionTypeFixedResponse,
+								FixedResponseConfig: &elbv2model.FixedResponseActionConfig{
+									StatusCode:  "404",
+									MessageBody: awssdk.String("Not found"),
+								},
+							},
+						},
+					},
+				},
+			},
+			want: []Rule{
+				{
+					Conditions: []elbv2model.RuleCondition{
+						{
+							Field: elbv2model.RuleConditionFieldHostHeader,
+							HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+								Values: []string{"a.example.com"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldPathPattern,
+							PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+								RegexValues: []string{"^/.*$"},
+							},
+						},
+					},
+					Actions: []elbv2model.Action{
+						{
+							Type: elbv2model.ActionTypeRedirect,
+							RedirectConfig: &elbv2model.RedirectActionConfig{
+								Host:       awssdk.String("default.example.com"),
+								Path:       awssdk.String("/#{path}"),
+								StatusCode: "HTTP_302",
+							},
+						},
+					},
+				},
+				{
+					Conditions: []elbv2model.RuleCondition{
+						{
+							Field: elbv2model.RuleConditionFieldHostHeader,
+							HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+								Values: []string{"a.example.com"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldPathPattern,
+							PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+								RegexValues: []string{"^/api/.*"},
+							},
+						},
+					},
+					Actions: []elbv2model.Action{
+						{
+							Type: elbv2model.ActionTypeFixedResponse,
+							FixedResponseConfig: &elbv2model.FixedResponseActionConfig{
+								StatusCode:  "404",
+								MessageBody: awssdk.String("Not found"),
+							},
+						},
+					},
+				},
+			},
+		},
+		{
+			name: "identical regex paths with different actions should be deduplicated",
+			args: args{
+				port:     443,
+				protocol: elbv2model.ProtocolHTTPS,
+				rules: []Rule{
+					{
+						Conditions: []elbv2model.RuleCondition{
+							{
+								Field: elbv2model.RuleConditionFieldHostHeader,
+								HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+									Values: []string{"a.example.com"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldPathPattern,
+								PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+									RegexValues: []string{"^/(sos/packages/embed-button)/.*$"},
+								},
+							},
+						},
+						Actions: []elbv2model.Action{
+							{
+								Type: elbv2model.ActionTypeRedirect,
+								RedirectConfig: &elbv2model.RedirectActionConfig{
+									Host:       awssdk.String("b.example.com"),
+									Path:       awssdk.String("/#{path}"),
+									StatusCode: "HTTP_302",
+								},
+							},
+						},
+					},
+					{
+						Conditions: []elbv2model.RuleCondition{
+							{
+								Field: elbv2model.RuleConditionFieldHostHeader,
+								HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+									Values: []string{"a.example.com"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldPathPattern,
+								PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+									RegexValues: []string{"^/(sos/packages/embed-button)/.*$"},
+								},
+							},
+						},
+						Actions: []elbv2model.Action{
+							{
+								Type: elbv2model.ActionTypeFixedResponse,
+								FixedResponseConfig: &elbv2model.FixedResponseActionConfig{
+									StatusCode:  "403",
+									MessageBody: awssdk.String("403 permission denied"),
+								},
+							},
+						},
+					},
+				},
+			},
+			want: []Rule{
+				{
+					Conditions: []elbv2model.RuleCondition{
+						{
+							Field: elbv2model.RuleConditionFieldHostHeader,
+							HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+								Values: []string{"a.example.com"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldPathPattern,
+							PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+								RegexValues: []string{"^/(sos/packages/embed-button)/.*$"},
+							},
+						},
+					},
+					Actions: []elbv2model.Action{
+						{
+							Type: elbv2model.ActionTypeRedirect,
+							RedirectConfig: &elbv2model.RedirectActionConfig{
+								Host:       awssdk.String("b.example.com"),
+								Path:       awssdk.String("/#{path}"),
+								StatusCode: "HTTP_302",
+							},
+						},
+					},
+				},
+			},
+		},
+		{
+			name: "two different regex paths with redirect actions should be preserved",
+			args: args{
+				port:     443,
+				protocol: elbv2model.ProtocolHTTPS,
+				rules: []Rule{
+					{
+						Conditions: []elbv2model.RuleCondition{
+							{
+								Field: elbv2model.RuleConditionFieldHostHeader,
+								HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+									Values: []string{"a.example.com"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldPathPattern,
+								PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+									RegexValues: []string{"^/w/(custom_pin_code|form|survey)/?$"},
+								},
+							},
+						},
+						Actions: []elbv2model.Action{
+							{
+								Type: elbv2model.ActionTypeRedirect,
+								RedirectConfig: &elbv2model.RedirectActionConfig{
+									Host:       awssdk.String("b.example.com"),
+									Path:       awssdk.String("/#{path}/not-found"),
+									Protocol:   awssdk.String("HTTPS"),
+									Port:       awssdk.String("443"),
+									StatusCode: "HTTP_302",
+								},
+							},
+						},
+					},
+					{
+						Conditions: []elbv2model.RuleCondition{
+							{
+								Field: elbv2model.RuleConditionFieldHostHeader,
+								HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+									Values: []string{"a.example.com"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldPathPattern,
+								PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+									RegexValues: []string{"^/(w/(survey|form|custom_pin_code)|sos/packages/embed-button)/.*"},
+								},
+							},
+						},
+						Actions: []elbv2model.Action{
+							{
+								Type: elbv2model.ActionTypeRedirect,
+								RedirectConfig: &elbv2model.RedirectActionConfig{
+									Host:       awssdk.String("b.example.com"),
+									Path:       awssdk.String("/#{path}"),
+									Protocol:   awssdk.String("HTTPS"),
+									Port:       awssdk.String("443"),
+									StatusCode: "HTTP_302",
+								},
+							},
+						},
+					},
+				},
+			},
+			want: []Rule{
+				{
+					Conditions: []elbv2model.RuleCondition{
+						{
+							Field: elbv2model.RuleConditionFieldHostHeader,
+							HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+								Values: []string{"a.example.com"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldPathPattern,
+							PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+								RegexValues: []string{"^/w/(custom_pin_code|form|survey)/?$"},
+							},
+						},
+					},
+					Actions: []elbv2model.Action{
+						{
+							Type: elbv2model.ActionTypeRedirect,
+							RedirectConfig: &elbv2model.RedirectActionConfig{
+								Host:       awssdk.String("b.example.com"),
+								Path:       awssdk.String("/#{path}/not-found"),
+								Protocol:   awssdk.String("HTTPS"),
+								Port:       awssdk.String("443"),
+								StatusCode: "HTTP_302",
+							},
+						},
+					},
+				},
+				{
+					Conditions: []elbv2model.RuleCondition{
+						{
+							Field: elbv2model.RuleConditionFieldHostHeader,
+							HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+								Values: []string{"a.example.com"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldPathPattern,
+							PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+								RegexValues: []string{"^/(w/(survey|form|custom_pin_code)|sos/packages/embed-button)/.*"},
+							},
+						},
+					},
+					Actions: []elbv2model.Action{
+						{
+							Type: elbv2model.ActionTypeRedirect,
+							RedirectConfig: &elbv2model.RedirectActionConfig{
+								Host:       awssdk.String("b.example.com"),
+								Path:       awssdk.String("/#{path}"),
+								Protocol:   awssdk.String("HTTPS"),
+								Port:       awssdk.String("443"),
+								StatusCode: "HTTP_302",
+							},
+						},
+					},
+				},
+			},
+		},
+		{
+			name: "rules with different query strings should be preserved",
+			args: args{
+				port:     443,
+				protocol: elbv2model.ProtocolHTTPS,
+				rules: []Rule{
+					{
+						Conditions: []elbv2model.RuleCondition{
+							{
+								Field: elbv2model.RuleConditionFieldHostHeader,
+								HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+									Values: []string{"a.example.com"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldPathPattern,
+								PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+									Values: []string{"/api"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldQueryString,
+								QueryStringConfig: &elbv2model.QueryStringConditionConfig{
+									Values: []elbv2model.QueryStringKeyValuePair{
+										{Key: awssdk.String("version"), Value: "v1"},
+									},
+								},
+							},
+						},
+						Actions: []elbv2model.Action{
+							{
+								Type: elbv2model.ActionTypeRedirect,
+								RedirectConfig: &elbv2model.RedirectActionConfig{
+									Host:       awssdk.String("api-v1.example.com"),
+									StatusCode: "HTTP_302",
+								},
+							},
+						},
+					},
+					{
+						Conditions: []elbv2model.RuleCondition{
+							{
+								Field: elbv2model.RuleConditionFieldHostHeader,
+								HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+									Values: []string{"a.example.com"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldPathPattern,
+								PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+									Values: []string{"/api"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldQueryString,
+								QueryStringConfig: &elbv2model.QueryStringConditionConfig{
+									Values: []elbv2model.QueryStringKeyValuePair{
+										{Key: awssdk.String("version"), Value: "v2"},
+									},
+								},
+							},
+						},
+						Actions: []elbv2model.Action{
+							{
+								Type: elbv2model.ActionTypeRedirect,
+								RedirectConfig: &elbv2model.RedirectActionConfig{
+									Host:       awssdk.String("api-v2.example.com"),
+									StatusCode: "HTTP_302",
+								},
+							},
+						},
+					},
+				},
+			},
+			want: []Rule{
+				{
+					Conditions: []elbv2model.RuleCondition{
+						{
+							Field: elbv2model.RuleConditionFieldHostHeader,
+							HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+								Values: []string{"a.example.com"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldPathPattern,
+							PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+								Values: []string{"/api"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldQueryString,
+							QueryStringConfig: &elbv2model.QueryStringConditionConfig{
+								Values: []elbv2model.QueryStringKeyValuePair{
+									{Key: awssdk.String("version"), Value: "v1"},
+								},
+							},
+						},
+					},
+					Actions: []elbv2model.Action{
+						{
+							Type: elbv2model.ActionTypeRedirect,
+							RedirectConfig: &elbv2model.RedirectActionConfig{
+								Host:       awssdk.String("api-v1.example.com"),
+								StatusCode: "HTTP_302",
+							},
+						},
+					},
+				},
+				{
+					Conditions: []elbv2model.RuleCondition{
+						{
+							Field: elbv2model.RuleConditionFieldHostHeader,
+							HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+								Values: []string{"a.example.com"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldPathPattern,
+							PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+								Values: []string{"/api"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldQueryString,
+							QueryStringConfig: &elbv2model.QueryStringConditionConfig{
+								Values: []elbv2model.QueryStringKeyValuePair{
+									{Key: awssdk.String("version"), Value: "v2"},
+								},
+							},
+						},
+					},
+					Actions: []elbv2model.Action{
+						{
+							Type: elbv2model.ActionTypeRedirect,
+							RedirectConfig: &elbv2model.RedirectActionConfig{
+								Host:       awssdk.String("api-v2.example.com"),
+								StatusCode: "HTTP_302",
+							},
+						},
+					},
+				},
+			},
+		},
+		{
+			name: "rules with different HTTP methods should be preserved",
+			args: args{
+				port:     443,
+				protocol: elbv2model.ProtocolHTTPS,
+				rules: []Rule{
+					{
+						Conditions: []elbv2model.RuleCondition{
+							{
+								Field: elbv2model.RuleConditionFieldHostHeader,
+								HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+									Values: []string{"a.example.com"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldPathPattern,
+								PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+									Values: []string{"/api"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldHTTPRequestMethod,
+								HTTPRequestMethodConfig: &elbv2model.HTTPRequestMethodConditionConfig{
+									Values: []string{"GET"},
+								},
+							},
+						},
+						Actions: []elbv2model.Action{
+							{
+								Type: elbv2model.ActionTypeRedirect,
+								RedirectConfig: &elbv2model.RedirectActionConfig{
+									Host:       awssdk.String("readonly.example.com"),
+									StatusCode: "HTTP_302",
+								},
+							},
+						},
+					},
+					{
+						Conditions: []elbv2model.RuleCondition{
+							{
+								Field: elbv2model.RuleConditionFieldHostHeader,
+								HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+									Values: []string{"a.example.com"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldPathPattern,
+								PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+									Values: []string{"/api"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldHTTPRequestMethod,
+								HTTPRequestMethodConfig: &elbv2model.HTTPRequestMethodConditionConfig{
+									Values: []string{"POST"},
+								},
+							},
+						},
+						Actions: []elbv2model.Action{
+							{
+								Type: elbv2model.ActionTypeRedirect,
+								RedirectConfig: &elbv2model.RedirectActionConfig{
+									Host:       awssdk.String("writeapi.example.com"),
+									StatusCode: "HTTP_302",
+								},
+							},
+						},
+					},
+				},
+			},
+			want: []Rule{
+				{
+					Conditions: []elbv2model.RuleCondition{
+						{
+							Field: elbv2model.RuleConditionFieldHostHeader,
+							HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+								Values: []string{"a.example.com"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldPathPattern,
+							PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+								Values: []string{"/api"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldHTTPRequestMethod,
+							HTTPRequestMethodConfig: &elbv2model.HTTPRequestMethodConditionConfig{
+								Values: []string{"GET"},
+							},
+						},
+					},
+					Actions: []elbv2model.Action{
+						{
+							Type: elbv2model.ActionTypeRedirect,
+							RedirectConfig: &elbv2model.RedirectActionConfig{
+								Host:       awssdk.String("readonly.example.com"),
+								StatusCode: "HTTP_302",
+							},
+						},
+					},
+				},
+				{
+					Conditions: []elbv2model.RuleCondition{
+						{
+							Field: elbv2model.RuleConditionFieldHostHeader,
+							HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+								Values: []string{"a.example.com"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldPathPattern,
+							PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+								Values: []string{"/api"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldHTTPRequestMethod,
+							HTTPRequestMethodConfig: &elbv2model.HTTPRequestMethodConditionConfig{
+								Values: []string{"POST"},
+							},
+						},
+					},
+					Actions: []elbv2model.Action{
+						{
+							Type: elbv2model.ActionTypeRedirect,
+							RedirectConfig: &elbv2model.RedirectActionConfig{
+								Host:       awssdk.String("writeapi.example.com"),
+								StatusCode: "HTTP_302",
+							},
+						},
+					},
+				},
+			},
+		},
+		{
+			name: "rules with different source IPs should be preserved",
+			args: args{
+				port:     443,
+				protocol: elbv2model.ProtocolHTTPS,
+				rules: []Rule{
+					{
+						Conditions: []elbv2model.RuleCondition{
+							{
+								Field: elbv2model.RuleConditionFieldHostHeader,
+								HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+									Values: []string{"a.example.com"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldPathPattern,
+								PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+									Values: []string{"/admin"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldSourceIP,
+								SourceIPConfig: &elbv2model.SourceIPConditionConfig{
+									Values: []string{"10.0.0.0/8"},
+								},
+							},
+						},
+						Actions: []elbv2model.Action{
+							{
+								Type: elbv2model.ActionTypeRedirect,
+								RedirectConfig: &elbv2model.RedirectActionConfig{
+									Host:       awssdk.String("internal-admin.example.com"),
+									StatusCode: "HTTP_302",
+								},
+							},
+						},
+					},
+					{
+						Conditions: []elbv2model.RuleCondition{
+							{
+								Field: elbv2model.RuleConditionFieldHostHeader,
+								HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+									Values: []string{"a.example.com"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldPathPattern,
+								PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+									Values: []string{"/admin"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldSourceIP,
+								SourceIPConfig: &elbv2model.SourceIPConditionConfig{
+									Values: []string{"192.168.0.0/16"},
+								},
+							},
+						},
+						Actions: []elbv2model.Action{
+							{
+								Type: elbv2model.ActionTypeRedirect,
+								RedirectConfig: &elbv2model.RedirectActionConfig{
+									Host:       awssdk.String("vpn-admin.example.com"),
+									StatusCode: "HTTP_302",
+								},
+							},
+						},
+					},
+				},
+			},
+			want: []Rule{
+				{
+					Conditions: []elbv2model.RuleCondition{
+						{
+							Field: elbv2model.RuleConditionFieldHostHeader,
+							HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+								Values: []string{"a.example.com"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldPathPattern,
+							PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+								Values: []string{"/admin"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldSourceIP,
+							SourceIPConfig: &elbv2model.SourceIPConditionConfig{
+								Values: []string{"10.0.0.0/8"},
+							},
+						},
+					},
+					Actions: []elbv2model.Action{
+						{
+							Type: elbv2model.ActionTypeRedirect,
+							RedirectConfig: &elbv2model.RedirectActionConfig{
+								Host:       awssdk.String("internal-admin.example.com"),
+								StatusCode: "HTTP_302",
+							},
+						},
+					},
+				},
+				{
+					Conditions: []elbv2model.RuleCondition{
+						{
+							Field: elbv2model.RuleConditionFieldHostHeader,
+							HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+								Values: []string{"a.example.com"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldPathPattern,
+							PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+								Values: []string{"/admin"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldSourceIP,
+							SourceIPConfig: &elbv2model.SourceIPConditionConfig{
+								Values: []string{"192.168.0.0/16"},
+							},
+						},
+					},
+					Actions: []elbv2model.Action{
+						{
+							Type: elbv2model.ActionTypeRedirect,
+							RedirectConfig: &elbv2model.RedirectActionConfig{
+								Host:       awssdk.String("vpn-admin.example.com"),
+								StatusCode: "HTTP_302",
+							},
+						},
+					},
+				},
+			},
+		},
+		{
+			name: "complex scenario with mixed condition types",
+			args: args{
+				port:     443,
+				protocol: elbv2model.ProtocolHTTPS,
+				rules: []Rule{
+					{
+						Conditions: []elbv2model.RuleCondition{
+							{
+								Field: elbv2model.RuleConditionFieldHostHeader,
+								HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+									Values: []string{"a.example.com"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldPathPattern,
+								PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+									RegexValues: []string{"^/api/v[1-2]/users.*"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldHTTPRequestMethod,
+								HTTPRequestMethodConfig: &elbv2model.HTTPRequestMethodConditionConfig{
+									Values: []string{"GET"},
+								},
+							},
+						},
+						Actions: []elbv2model.Action{
+							{
+								Type: elbv2model.ActionTypeRedirect,
+								RedirectConfig: &elbv2model.RedirectActionConfig{
+									Host:       awssdk.String("users-api.example.com"),
+									Path:       awssdk.String("/#{path}"),
+									StatusCode: "HTTP_302",
+								},
+							},
+						},
+					},
+					{
+						Conditions: []elbv2model.RuleCondition{
+							{
+								Field: elbv2model.RuleConditionFieldHostHeader,
+								HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+									Values: []string{"a.example.com"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldPathPattern,
+								PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+									RegexValues: []string{"^/api/v3/.*"},
+								},
+							},
+							{
+								Field: elbv2model.RuleConditionFieldQueryString,
+								QueryStringConfig: &elbv2model.QueryStringConditionConfig{
+									Values: []elbv2model.QueryStringKeyValuePair{
+										{Key: awssdk.String("beta"), Value: "true"},
+									},
+								},
+							},
+						},
+						Actions: []elbv2model.Action{
+							{
+								Type: elbv2model.ActionTypeRedirect,
+								RedirectConfig: &elbv2model.RedirectActionConfig{
+									Host:       awssdk.String("beta-api.example.com"),
+									Path:       awssdk.String("/#{path}"),
+									StatusCode: "HTTP_302",
+								},
+							},
+						},
+					},
+				},
+			},
+			want: []Rule{
+				{
+					Conditions: []elbv2model.RuleCondition{
+						{
+							Field: elbv2model.RuleConditionFieldHostHeader,
+							HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+								Values: []string{"a.example.com"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldPathPattern,
+							PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+								RegexValues: []string{"^/api/v[1-2]/users.*"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldHTTPRequestMethod,
+							HTTPRequestMethodConfig: &elbv2model.HTTPRequestMethodConditionConfig{
+								Values: []string{"GET"},
+							},
+						},
+					},
+					Actions: []elbv2model.Action{
+						{
+							Type: elbv2model.ActionTypeRedirect,
+							RedirectConfig: &elbv2model.RedirectActionConfig{
+								Host:       awssdk.String("users-api.example.com"),
+								Path:       awssdk.String("/#{path}"),
+								StatusCode: "HTTP_302",
+							},
+						},
+					},
+				},
+				{
+					Conditions: []elbv2model.RuleCondition{
+						{
+							Field: elbv2model.RuleConditionFieldHostHeader,
+							HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+								Values: []string{"a.example.com"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldPathPattern,
+							PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+								RegexValues: []string{"^/api/v3/.*"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldQueryString,
+							QueryStringConfig: &elbv2model.QueryStringConditionConfig{
+								Values: []elbv2model.QueryStringKeyValuePair{
+									{Key: awssdk.String("beta"), Value: "true"},
+								},
+							},
+						},
+					},
+					Actions: []elbv2model.Action{
+						{
+							Type: elbv2model.ActionTypeRedirect,
+							RedirectConfig: &elbv2model.RedirectActionConfig{
+								Host:       awssdk.String("beta-api.example.com"),
+								Path:       awssdk.String("/#{path}"),
+								StatusCode: "HTTP_302",
+							},
+						},
+					},
+				},
+			},
+		},
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
@@ -248,6 +1128,120 @@ func Test_defaultRuleOptimizer_Optimize(t *testing.T) {
 	}
 }
 
+// TestIsSupersetConditions_DifferentRegexPaths tests that different regex paths are NOT considered supersets
+func TestIsSupersetConditions_DifferentRegexPaths(t *testing.T) {
+	tests := []struct {
+		name     string
+		lhsRules []elbv2model.RuleCondition
+		rhsRules []elbv2model.RuleCondition
+		expected bool
+	}{
+		{
+			name: "Different regex paths should NOT be supersets",
+			lhsRules: []elbv2model.RuleCondition{
+				{
+					Field: elbv2model.RuleConditionFieldPathPattern,
+					PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+						RegexValues: []string{"^/w/(custom_pin_code|form|survey)/?$"},
+					},
+				},
+				{
+					Field: elbv2model.RuleConditionFieldHostHeader,
+					HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+						Values: []string{"a.example.com"},
+					},
+				},
+			},
+			rhsRules: []elbv2model.RuleCondition{
+				{
+					Field: elbv2model.RuleConditionFieldPathPattern,
+					PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+						RegexValues: []string{"^/(w/(survey|form|custom_pin_code)|sos/packages/embed-button)/.*"},
+					},
+				},
+				{
+					Field: elbv2model.RuleConditionFieldHostHeader,
+					HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+						Values: []string{"a.example.com"},
+					},
+				},
+			},
+			expected: false, // Different regex patterns should NOT be superset
+		},
+		{
+			name: "Identical regex paths should be supersets",
+			lhsRules: []elbv2model.RuleCondition{
+				{
+					Field: elbv2model.RuleConditionFieldPathPattern,
+					PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+						RegexValues: []string{"^/(sos/packages/embed-button)/.*$"},
+					},
+				},
+				{
+					Field: elbv2model.RuleConditionFieldHostHeader,
+					HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+						Values: []string{"a.example.com"},
+					},
+				},
+			},
+			rhsRules: []elbv2model.RuleCondition{
+				{
+					Field: elbv2model.RuleConditionFieldPathPattern,
+					PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+						RegexValues: []string{"^/(sos/packages/embed-button)/.*$"},
+					},
+				},
+				{
+					Field: elbv2model.RuleConditionFieldHostHeader,
+					HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+						Values: []string{"a.example.com"},
+					},
+				},
+			},
+			expected: true, // Identical regex patterns should be superset
+		},
+		{
+			name: "Catch-all regex with other paths",
+			lhsRules: []elbv2model.RuleCondition{
+				{
+					Field: elbv2model.RuleConditionFieldPathPattern,
+					PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+						RegexValues: []string{"^/.*$"},
+					},
+				},
+				{
+					Field: elbv2model.RuleConditionFieldHostHeader,
+					HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+						Values: []string{"a.example.com"},
+					},
+				},
+			},
+			rhsRules: []elbv2model.RuleCondition{
+				{
+					Field: elbv2model.RuleConditionFieldPathPattern,
+					PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+						RegexValues: []string{"^/specific/path$"},
+					},
+				},
+				{
+					Field: elbv2model.RuleConditionFieldHostHeader,
+					HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+						Values: []string{"a.example.com"},
+					},
+				},
+			},
+			expected: false, // Different regex patterns, not superset
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			result := isSupersetConditions(tt.lhsRules, tt.rhsRules)
+			assert.Equal(t, tt.expected, result)
+		})
+	}
+}
+
 func Test_isInfiniteRedirectRule(t *testing.T) {
 	type args struct {
 		port     int32
@@ -291,6 +1285,38 @@ func Test_isInfiniteRedirectRule(t *testing.T) {
 			},
 			want: true,
 		},
+		{
+			name: "isnt infinite redirect rule when for regex paths",
+			args: args{
+				port:     443,
+				protocol: elbv2model.ProtocolHTTPS,
+				rule: Rule{
+					Conditions: []elbv2model.RuleCondition{
+						{
+							Field: elbv2model.RuleConditionFieldHostHeader,
+							HostHeaderConfig: &elbv2model.HostHeaderConditionConfig{
+								Values: []string{"www.example.com", "app.example.com"},
+							},
+						},
+						{
+							Field: elbv2model.RuleConditionFieldPathPattern,
+							PathPatternConfig: &elbv2model.PathPatternConditionConfig{
+								RegexValues: []string{"^/specific/path$"},
+							},
+						},
+					},
+					Actions: []elbv2model.Action{
+						{
+							Type: elbv2model.ActionTypeRedirect,
+							RedirectConfig: &elbv2model.RedirectActionConfig{
+								StatusCode: "HTTP_301",
+							},
+						},
+					},
+				},
+			},
+			want: false,
+		},
 		{
 			name: "is infinite redirect rule when all fields are set to default value",
 			args: args{
diff --git a/pkg/runtime/retry_utils.go b/pkg/runtime/retry_utils.go
index 38a2f3370a..1c12074d18 100644
--- a/pkg/runtime/retry_utils.go
+++ b/pkg/runtime/retry_utils.go
@@ -1,20 +1,29 @@
 package runtime
 
 import (
-	"k8s.io/apimachinery/pkg/util/wait"
+	"fmt"
 	"time"
+
+	"k8s.io/apimachinery/pkg/util/wait"
 )
 
 // RetryImmediateOnError tries to run fn every interval until it succeeds, a non-retryable error occurs or the timeout is reached.
+// If the timeout is reached while retrying, the returned error wraps both the timeout and the last retryable error.
 func RetryImmediateOnError(interval time.Duration, timeout time.Duration, retryable func(error) bool, fn func() error) error {
-	return wait.PollImmediate(interval, timeout, func() (bool, error) {
+	var lastRetryableErr error
+	err := wait.PollImmediate(interval, timeout, func() (bool, error) {
 		err := fn()
 		if err != nil {
 			if retryable(err) {
+				lastRetryableErr = err
 				return false, nil
 			}
 			return false, err
 		}
 		return true, nil
 	})
+	if wait.Interrupted(err) && lastRetryableErr != nil {
+		return fmt.Errorf("%w: %v", err, lastRetryableErr)
+	}
+	return err
 }
diff --git a/pkg/runtime/retry_utils_test.go b/pkg/runtime/retry_utils_test.go
index b1ac0a1d7a..85f2581d5c 100644
--- a/pkg/runtime/retry_utils_test.go
+++ b/pkg/runtime/retry_utils_test.go
@@ -2,9 +2,10 @@ package runtime
 
 import (
 	"errors"
-	"github.com/stretchr/testify/assert"
 	"testing"
 	"time"
+
+	"github.com/stretchr/testify/assert"
 )
 
 func Test_RetryImmediateOnError(t *testing.T) {
@@ -38,54 +39,63 @@ func Test_RetryImmediateOnError(t *testing.T) {
 		fn        func() error
 	}
 	tests := []struct {
-		name      string
-		args      args
-		wantCount int
-		wantErr   error
+		name         string
+		args         args
+		wantMinCount int
+		wantMaxCount int
+		wantErr      error
 	}{
 		{
 			name: "retry 4 times before failure",
 			args: args{
-				interval:  10 * time.Millisecond,
-				timeout:   100 * time.Millisecond,
+				interval:  50 * time.Millisecond,
+				timeout:   500 * time.Millisecond,
 				retryable: retryable,
 				fn:        failureAfterRetryCountFnGen(4),
 			},
-			wantCount: 5,
-			wantErr:   errors.New("failure"),
+			wantMinCount: 5,
+			wantMaxCount: 5,
+			wantErr:      errors.New("failure"),
 		},
 		{
 			name: "retry 4 times before failure - but timeout after 2nd retry",
 			args: args{
-				interval:  10 * time.Millisecond,
-				timeout:   19 * time.Millisecond,
+				interval:  50 * time.Millisecond,
+				timeout:   120 * time.Millisecond,
 				retryable: retryable,
 				fn:        failureAfterRetryCountFnGen(4),
 			},
-			wantCount: 3,
-			wantErr:   errors.New("timed out waiting for the condition"),
+			// PollImmediate calls fn at t=0, t=50ms, t=100ms. Timeout at 120ms
+			// may race with the next tick, so count can be 3 or 4.
+			wantMinCount: 3,
+			wantMaxCount: 4,
+			wantErr:      errors.New("timed out waiting for the condition: retryable"),
 		},
 		{
 			name: "retry 4 times before success",
 			args: args{
-				interval:  10 * time.Millisecond,
-				timeout:   100 * time.Millisecond,
+				interval:  50 * time.Millisecond,
+				timeout:   500 * time.Millisecond,
 				retryable: retryable,
 				fn:        successAfterRetryCountFnGen(4),
 			},
-			wantCount: 5,
-			wantErr:   nil,
+			wantMinCount: 5,
+			wantMaxCount: 5,
+			wantErr:      nil,
 		},
 		{
 			name: "retry 4 times before success - but timeout after 2nd retry",
 			args: args{
-				interval:  10 * time.Millisecond,
-				timeout:   19 * time.Millisecond,
+				interval:  50 * time.Millisecond,
+				timeout:   120 * time.Millisecond,
 				retryable: retryable,
 				fn:        successAfterRetryCountFnGen(4),
 			},
-			wantCount: 3,
-			wantErr:   errors.New("timed out waiting for the condition"),
+			// PollImmediate calls fn at t=0, t=50ms, t=100ms. Timeout at 120ms
+			// may race with the next tick, so count can be 3 or 4.
+			wantMinCount: 3,
+			wantMaxCount: 4,
+			wantErr:      errors.New("timed out waiting for the condition: retryable"),
 		},
 	}
 	for _, tt := range tests {
@@ -100,7 +110,8 @@ func Test_RetryImmediateOnError(t *testing.T) {
 			} else {
 				assert.NoError(t, err)
 			}
-			assert.Equal(t, tt.wantCount, count)
+			assert.GreaterOrEqual(t, count, tt.wantMinCount, "retry count below minimum")
+			assert.LessOrEqual(t, count, tt.wantMaxCount, "retry count above maximum")
 		})
 	}
 }