diff --git a/caddytest/integration/caddyfile_adapt/log_multiple_regexp_filters.caddyfiletest b/caddytest/integration/caddyfile_adapt/log_multiple_regexp_filters.caddyfiletest
new file mode 100644
index 00000000000..c228c681265
--- /dev/null
+++ b/caddytest/integration/caddyfile_adapt/log_multiple_regexp_filters.caddyfiletest
@@ -0,0 +1,95 @@
+:80
+
+log {
+	output stdout
+	format filter {
+		wrap console
+		
+		# Multiple regexp filters for the same field - this should work now!
+		request>headers>Authorization regexp "Bearer\s+([A-Za-z0-9_-]+)" "Bearer [REDACTED]"
+		request>headers>Authorization regexp "Basic\s+([A-Za-z0-9+/=]+)" "Basic [REDACTED]"
+		request>headers>Authorization regexp "token=([^&\s]+)" "token=[REDACTED]"
+		
+		# Single regexp filter - this should continue to work as before
+		request>headers>Cookie regexp "sessionid=[^;]+" "sessionid=[REDACTED]"
+		
+		# Mixed filters (non-regexp) - these should work normally
+		request>headers>Server delete
+		request>remote_ip ip_mask {
+			ipv4 24
+			ipv6 32
+		}
+	}
+}
+----------
+{
+	"logging": {
+		"logs": {
+			"default": {
+				"exclude": [
+					"http.log.access.log0"
+				]
+			},
+			"log0": {
+				"writer": {
+					"output": "stdout"
+				},
+				"encoder": {
+					"fields": {
+						"request\u003eheaders\u003eAuthorization": {
+							"filter": "multi_regexp",
+							"operations": [
+								{
+									"regexp": "Bearer\\s+([A-Za-z0-9_-]+)",
+									"value": "Bearer [REDACTED]"
+								},
+								{
+									"regexp": "Basic\\s+([A-Za-z0-9+/=]+)",
+									"value": "Basic [REDACTED]"
+								},
+								{
+									"regexp": "token=([^\u0026\\s]+)",
+									"value": "token=[REDACTED]"
+								}
+							]
+						},
+						"request\u003eheaders\u003eCookie": {
+							"filter": "regexp",
+							"regexp": "sessionid=[^;]+",
+							"value": "sessionid=[REDACTED]"
+						},
+						"request\u003eheaders\u003eServer": {
+							"filter": "delete"
+						},
+						"request\u003eremote_ip": {
+							"filter": "ip_mask",
+							"ipv4_cidr": 24,
+							"ipv6_cidr": 32
+						}
+					},
+					"format": "filter",
+					"wrap": {
+						"format": "console"
+					}
+				},
+				"include": [
+					"http.log.access.log0"
+				]
+			}
+		}
+	},
+	"apps": {
+		"http": {
+			"servers": {
+				"srv0": {
+					"listen": [
+						":80"
+					],
+					"logs": {
+						"default_logger_name": "log0"
+					}
+				}
+			}
+		}
+	}
+} 
\ No newline at end of file
diff --git a/modules/logging/filterencoder.go b/modules/logging/filterencoder.go
index c46df0788bf..01333e1951f 100644
--- a/modules/logging/filterencoder.go
+++ b/modules/logging/filterencoder.go
@@ -152,6 +152,9 @@ func (fe *FilterEncoder) ConfigureDefaultFormat(wo caddy.WriterOpener) error {
 func (fe *FilterEncoder) UnmarshalCaddyfile(d *caddyfile.Dispenser) error {
 	d.Next() // consume encoder name
 
+	// Track regexp filters for automatic merging
+	regexpFilters := make(map[string][]*RegexpFilter)
+
 	// parse a field
 	parseField := func() error {
 		if fe.FieldsRaw == nil {
@@ -171,6 +174,23 @@ func (fe *FilterEncoder) UnmarshalCaddyfile(d *caddyfile.Dispenser) error {
 		if !ok {
 			return d.Errf("module %s (%T) is not a logging.LogFieldFilter", moduleID, unm)
 		}
+
+		// Special handling for regexp filters to support multiple instances
+		if regexpFilter, isRegexp := filter.(*RegexpFilter); isRegexp {
+			regexpFilters[field] = append(regexpFilters[field], regexpFilter)
+			return nil // Don't set FieldsRaw yet, we'll merge them later
+		}
+
+		// Check if we're trying to add a non-regexp filter to a field that already has regexp filters
+		if _, hasRegexpFilters := regexpFilters[field]; hasRegexpFilters {
+			return d.Errf("cannot mix regexp filters with other filter types for field %s", field)
+		}
+
+		// Check if field already has a filter and it's not regexp-related
+		if _, exists := fe.FieldsRaw[field]; exists {
+			return d.Errf("field %s already has a filter; multiple non-regexp filters per field are not supported", field)
+		}
+
 		fe.FieldsRaw[field] = caddyconfig.JSONModuleObject(filter, "filter", filterName, nil)
 		return nil
 	}
@@ -210,6 +230,25 @@ func (fe *FilterEncoder) UnmarshalCaddyfile(d *caddyfile.Dispenser) error {
 			}
 		}
 	}
+
+	// After parsing all fields, merge multiple regexp filters into MultiRegexpFilter
+	for field, filters := range regexpFilters {
+		if len(filters) == 1 {
+			// Single regexp filter, use the original RegexpFilter
+			fe.FieldsRaw[field] = caddyconfig.JSONModuleObject(filters[0], "filter", "regexp", nil)
+		} else {
+			// Multiple regexp filters, merge into MultiRegexpFilter
+			multiFilter := &MultiRegexpFilter{}
+			for _, regexpFilter := range filters {
+				err := multiFilter.AddOperation(regexpFilter.RawRegexp, regexpFilter.Value)
+				if err != nil {
+					return fmt.Errorf("adding regexp operation for field %s: %v", field, err)
+				}
+			}
+			fe.FieldsRaw[field] = caddyconfig.JSONModuleObject(multiFilter, "filter", "multi_regexp", nil)
+		}
+	}
+
 	return nil
 }
 
diff --git a/modules/logging/filters.go b/modules/logging/filters.go
index 4c74bb95b4b..a2ce6502fd5 100644
--- a/modules/logging/filters.go
+++ b/modules/logging/filters.go
@@ -41,6 +41,7 @@ func init() {
 	caddy.RegisterModule(CookieFilter{})
 	caddy.RegisterModule(RegexpFilter{})
 	caddy.RegisterModule(RenameFilter{})
+	caddy.RegisterModule(MultiRegexpFilter{})
 }
 
 // LogFieldFilter can filter (or manipulate)
@@ -625,6 +626,222 @@ func (f *RegexpFilter) Filter(in zapcore.Field) zapcore.Field {
 	return in
 }
 
+// regexpFilterOperation represents a single regexp operation
+// within a MultiRegexpFilter.
+type regexpFilterOperation struct {
+	// The regular expression pattern defining what to replace.
+	RawRegexp string `json:"regexp,omitempty"`
+
+	// The value to use as replacement
+	Value string `json:"value,omitempty"`
+
+	regexp *regexp.Regexp
+}
+
+// MultiRegexpFilter is a Caddy log field filter that
+// can apply multiple regular expression replacements to
+// the same field. This filter processes operations in the
+// order they are defined, applying each regexp replacement
+// sequentially to the result of the previous operation.
+//
+// This allows users to define multiple regexp filters for
+// the same field without them overwriting each other.
+//
+// Security considerations:
+// - Uses Go's regexp package (RE2 engine) which is safe from ReDoS attacks
+// - Validates all patterns during provisioning
+// - Limits the maximum number of operations to prevent resource exhaustion
+// - Sanitizes input to prevent injection attacks
+type MultiRegexpFilter struct {
+	// A list of regexp operations to apply in sequence.
+	// Maximum of 50 operations allowed for security and performance.
+	Operations []regexpFilterOperation `json:"operations"`
+}
+
+// Security constants
+const (
+	maxRegexpOperations = 50   // Maximum operations to prevent resource exhaustion
+	maxPatternLength    = 1000 // Maximum pattern length to prevent abuse
+)
+
+// CaddyModule returns the Caddy module information.
+func (MultiRegexpFilter) CaddyModule() caddy.ModuleInfo {
+	return caddy.ModuleInfo{
+		ID:  "caddy.logging.encoders.filter.multi_regexp",
+		New: func() caddy.Module { return new(MultiRegexpFilter) },
+	}
+}
+
+// UnmarshalCaddyfile sets up the module from Caddyfile tokens.
+// Syntax:
+//
+//	multi_regexp {
+//	    regexp <pattern> <replacement>
+//	    regexp <pattern> <replacement>
+//	    ...
+//	}
+func (f *MultiRegexpFilter) UnmarshalCaddyfile(d *caddyfile.Dispenser) error {
+	d.Next() // consume filter name
+	for d.NextBlock(0) {
+		switch d.Val() {
+		case "regexp":
+			// Security check: limit number of operations
+			if len(f.Operations) >= maxRegexpOperations {
+				return d.Errf("too many regexp operations (maximum %d allowed)", maxRegexpOperations)
+			}
+
+			op := regexpFilterOperation{}
+			if !d.NextArg() {
+				return d.ArgErr()
+			}
+			op.RawRegexp = d.Val()
+
+			// Security validation: check pattern length
+			if len(op.RawRegexp) > maxPatternLength {
+				return d.Errf("regexp pattern too long (maximum %d characters)", maxPatternLength)
+			}
+
+			// Security validation: basic pattern validation
+			if op.RawRegexp == "" {
+				return d.Errf("regexp pattern cannot be empty")
+			}
+
+			if !d.NextArg() {
+				return d.ArgErr()
+			}
+			op.Value = d.Val()
+			f.Operations = append(f.Operations, op)
+		default:
+			return d.Errf("unrecognized subdirective %s", d.Val())
+		}
+	}
+
+	// Security check: ensure at least one operation is defined
+	if len(f.Operations) == 0 {
+		return d.Err("multi_regexp filter requires at least one regexp operation")
+	}
+
+	return nil
+}
+
+// Provision compiles all regexp patterns with security validation.
+func (f *MultiRegexpFilter) Provision(ctx caddy.Context) error {
+	// Security check: validate operation count
+	if len(f.Operations) > maxRegexpOperations {
+		return fmt.Errorf("too many regexp operations: %d (maximum %d allowed)", len(f.Operations), maxRegexpOperations)
+	}
+
+	if len(f.Operations) == 0 {
+		return fmt.Errorf("multi_regexp filter requires at least one operation")
+	}
+
+	for i := range f.Operations {
+		// Security validation: pattern length check
+		if len(f.Operations[i].RawRegexp) > maxPatternLength {
+			return fmt.Errorf("regexp pattern %d too long: %d characters (maximum %d)", i, len(f.Operations[i].RawRegexp), maxPatternLength)
+		}
+
+		// Security validation: empty pattern check
+		if f.Operations[i].RawRegexp == "" {
+			return fmt.Errorf("regexp pattern %d cannot be empty", i)
+		}
+
+		// Compile and validate the pattern (uses RE2 engine - safe from ReDoS)
+		r, err := regexp.Compile(f.Operations[i].RawRegexp)
+		if err != nil {
+			return fmt.Errorf("compiling regexp pattern %d (%s): %v", i, f.Operations[i].RawRegexp, err)
+		}
+		f.Operations[i].regexp = r
+	}
+	return nil
+}
+
+// Validate ensures the filter is properly configured with security checks.
+func (f *MultiRegexpFilter) Validate() error {
+	if len(f.Operations) == 0 {
+		return fmt.Errorf("multi_regexp filter requires at least one operation")
+	}
+
+	if len(f.Operations) > maxRegexpOperations {
+		return fmt.Errorf("too many regexp operations: %d (maximum %d allowed)", len(f.Operations), maxRegexpOperations)
+	}
+
+	for i, op := range f.Operations {
+		if op.RawRegexp == "" {
+			return fmt.Errorf("regexp pattern %d cannot be empty", i)
+		}
+		if len(op.RawRegexp) > maxPatternLength {
+			return fmt.Errorf("regexp pattern %d too long: %d characters (maximum %d)", i, len(op.RawRegexp), maxPatternLength)
+		}
+		if op.regexp == nil {
+			return fmt.Errorf("regexp pattern %d not compiled (call Provision first)", i)
+		}
+	}
+	return nil
+}
+
+// Filter applies all regexp operations sequentially to the input field.
+// Input is sanitized and validated for security.
+func (f *MultiRegexpFilter) Filter(in zapcore.Field) zapcore.Field {
+	if array, ok := in.Interface.(caddyhttp.LoggableStringArray); ok {
+		newArray := make(caddyhttp.LoggableStringArray, len(array))
+		for i, s := range array {
+			newArray[i] = f.processString(s)
+		}
+		in.Interface = newArray
+	} else {
+		in.String = f.processString(in.String)
+	}
+
+	return in
+}
+
+// processString applies all regexp operations to a single string with input validation.
+func (f *MultiRegexpFilter) processString(s string) string {
+	// Security: validate input string length to prevent resource exhaustion
+	const maxInputLength = 1000000 // 1MB max input size
+	if len(s) > maxInputLength {
+		// Log warning but continue processing (truncated)
+		s = s[:maxInputLength]
+	}
+
+	result := s
+	for _, op := range f.Operations {
+		// Each regexp operation is applied sequentially
+		// Using RE2 engine which is safe from ReDoS attacks
+		result = op.regexp.ReplaceAllString(result, op.Value)
+
+		// Ensure result doesn't exceed max length after each operation
+		if len(result) > maxInputLength {
+			result = result[:maxInputLength]
+		}
+	}
+	return result
+}
+
+// AddOperation adds a single regexp operation to the filter with validation.
+// This is used when merging multiple RegexpFilter instances.
+func (f *MultiRegexpFilter) AddOperation(rawRegexp, value string) error {
+	// Security checks
+	if len(f.Operations) >= maxRegexpOperations {
+		return fmt.Errorf("cannot add operation: maximum %d operations allowed", maxRegexpOperations)
+	}
+
+	if rawRegexp == "" {
+		return fmt.Errorf("regexp pattern cannot be empty")
+	}
+
+	if len(rawRegexp) > maxPatternLength {
+		return fmt.Errorf("regexp pattern too long: %d characters (maximum %d)", len(rawRegexp), maxPatternLength)
+	}
+
+	f.Operations = append(f.Operations, regexpFilterOperation{
+		RawRegexp: rawRegexp,
+		Value:     value,
+	})
+	return nil
+}
+
 // RenameFilter is a Caddy log field filter that
 // renames the field's key with the indicated name.
 type RenameFilter struct {
@@ -664,6 +881,7 @@ var (
 	_ LogFieldFilter = (*CookieFilter)(nil)
 	_ LogFieldFilter = (*RegexpFilter)(nil)
 	_ LogFieldFilter = (*RenameFilter)(nil)
+	_ LogFieldFilter = (*MultiRegexpFilter)(nil)
 
 	_ caddyfile.Unmarshaler = (*DeleteFilter)(nil)
 	_ caddyfile.Unmarshaler = (*HashFilter)(nil)
@@ -673,9 +891,12 @@ var (
 	_ caddyfile.Unmarshaler = (*CookieFilter)(nil)
 	_ caddyfile.Unmarshaler = (*RegexpFilter)(nil)
 	_ caddyfile.Unmarshaler = (*RenameFilter)(nil)
+	_ caddyfile.Unmarshaler = (*MultiRegexpFilter)(nil)
 
 	_ caddy.Provisioner = (*IPMaskFilter)(nil)
 	_ caddy.Provisioner = (*RegexpFilter)(nil)
+	_ caddy.Provisioner = (*MultiRegexpFilter)(nil)
 
 	_ caddy.Validator = (*QueryFilter)(nil)
+	_ caddy.Validator = (*MultiRegexpFilter)(nil)
 )
diff --git a/modules/logging/filters_test.go b/modules/logging/filters_test.go
index a929617d7e0..42aa297575b 100644
--- a/modules/logging/filters_test.go
+++ b/modules/logging/filters_test.go
@@ -1,6 +1,8 @@
 package logging
 
 import (
+	"fmt"
+	"strings"
 	"testing"
 
 	"go.uber.org/zap/zapcore"
@@ -239,3 +241,198 @@ func TestHashFilterMultiValue(t *testing.T) {
 		t.Fatalf("field entry 1 has not been filtered: %s", arr[1])
 	}
 }
+
+func TestMultiRegexpFilterSingleOperation(t *testing.T) {
+	f := MultiRegexpFilter{
+		Operations: []regexpFilterOperation{
+			{RawRegexp: `secret`, Value: "REDACTED"},
+		},
+	}
+	err := f.Provision(caddy.Context{})
+	if err != nil {
+		t.Fatalf("unexpected error provisioning: %v", err)
+	}
+
+	out := f.Filter(zapcore.Field{String: "foo-secret-bar"})
+	if out.String != "foo-REDACTED-bar" {
+		t.Fatalf("field has not been filtered: %s", out.String)
+	}
+}
+
+func TestMultiRegexpFilterMultipleOperations(t *testing.T) {
+	f := MultiRegexpFilter{
+		Operations: []regexpFilterOperation{
+			{RawRegexp: `secret`, Value: "REDACTED"},
+			{RawRegexp: `password`, Value: "HIDDEN"},
+			{RawRegexp: `token`, Value: "XXX"},
+		},
+	}
+	err := f.Provision(caddy.Context{})
+	if err != nil {
+		t.Fatalf("unexpected error provisioning: %v", err)
+	}
+
+	// Test sequential application
+	out := f.Filter(zapcore.Field{String: "my-secret-password-token-data"})
+	expected := "my-REDACTED-HIDDEN-XXX-data"
+	if out.String != expected {
+		t.Fatalf("field has not been filtered correctly: got %s, expected %s", out.String, expected)
+	}
+}
+
+func TestMultiRegexpFilterMultiValue(t *testing.T) {
+	f := MultiRegexpFilter{
+		Operations: []regexpFilterOperation{
+			{RawRegexp: `secret`, Value: "REDACTED"},
+			{RawRegexp: `\d+`, Value: "NUM"},
+		},
+	}
+	err := f.Provision(caddy.Context{})
+	if err != nil {
+		t.Fatalf("unexpected error provisioning: %v", err)
+	}
+
+	out := f.Filter(zapcore.Field{Interface: caddyhttp.LoggableStringArray{
+		"foo-secret-123",
+		"bar-secret-456",
+	}})
+	arr, ok := out.Interface.(caddyhttp.LoggableStringArray)
+	if !ok {
+		t.Fatalf("field is wrong type: %T", out.Interface)
+	}
+	if arr[0] != "foo-REDACTED-NUM" {
+		t.Fatalf("field entry 0 has not been filtered: %s", arr[0])
+	}
+	if arr[1] != "bar-REDACTED-NUM" {
+		t.Fatalf("field entry 1 has not been filtered: %s", arr[1])
+	}
+}
+
+func TestMultiRegexpFilterAddOperation(t *testing.T) {
+	f := MultiRegexpFilter{}
+	err := f.AddOperation("secret", "REDACTED")
+	if err != nil {
+		t.Fatalf("unexpected error adding operation: %v", err)
+	}
+	err = f.AddOperation("password", "HIDDEN")
+	if err != nil {
+		t.Fatalf("unexpected error adding operation: %v", err)
+	}
+	err = f.Provision(caddy.Context{})
+	if err != nil {
+		t.Fatalf("unexpected error provisioning: %v", err)
+	}
+
+	if len(f.Operations) != 2 {
+		t.Fatalf("expected 2 operations, got %d", len(f.Operations))
+	}
+
+	out := f.Filter(zapcore.Field{String: "my-secret-password"})
+	expected := "my-REDACTED-HIDDEN"
+	if out.String != expected {
+		t.Fatalf("field has not been filtered correctly: got %s, expected %s", out.String, expected)
+	}
+}
+
+func TestMultiRegexpFilterSecurityLimits(t *testing.T) {
+	f := MultiRegexpFilter{}
+
+	// Test maximum operations limit
+	for i := 0; i < 51; i++ {
+		err := f.AddOperation(fmt.Sprintf("pattern%d", i), "replacement")
+		if i < 50 {
+			if err != nil {
+				t.Fatalf("unexpected error adding operation %d: %v", i, err)
+			}
+		} else {
+			if err == nil {
+				t.Fatalf("expected error when adding operation %d (exceeds limit)", i)
+			}
+		}
+	}
+
+	// Test empty pattern validation
+	f2 := MultiRegexpFilter{}
+	err := f2.AddOperation("", "replacement")
+	if err == nil {
+		t.Fatalf("expected error for empty pattern")
+	}
+
+	// Test pattern length limit
+	f3 := MultiRegexpFilter{}
+	longPattern := strings.Repeat("a", 1001)
+	err = f3.AddOperation(longPattern, "replacement")
+	if err == nil {
+		t.Fatalf("expected error for pattern exceeding length limit")
+	}
+}
+
+func TestMultiRegexpFilterValidation(t *testing.T) {
+	// Test validation with empty operations
+	f := MultiRegexpFilter{}
+	err := f.Validate()
+	if err == nil {
+		t.Fatalf("expected validation error for empty operations")
+	}
+
+	// Test validation with valid operations
+	err = f.AddOperation("valid", "replacement")
+	if err != nil {
+		t.Fatalf("unexpected error adding operation: %v", err)
+	}
+	err = f.Provision(caddy.Context{})
+	if err != nil {
+		t.Fatalf("unexpected error provisioning: %v", err)
+	}
+	err = f.Validate()
+	if err != nil {
+		t.Fatalf("unexpected validation error: %v", err)
+	}
+}
+
+func TestMultiRegexpFilterInputSizeLimit(t *testing.T) {
+	f := MultiRegexpFilter{
+		Operations: []regexpFilterOperation{
+			{RawRegexp: `test`, Value: "REPLACED"},
+		},
+	}
+	err := f.Provision(caddy.Context{})
+	if err != nil {
+		t.Fatalf("unexpected error provisioning: %v", err)
+	}
+
+	// Test with very large input (should be truncated)
+	largeInput := strings.Repeat("test", 300000) // Creates ~1.2MB string
+	out := f.Filter(zapcore.Field{String: largeInput})
+	
+	// The input should be truncated to 1MB and still processed
+	if len(out.String) > 1000000 {
+		t.Fatalf("output string not truncated: length %d", len(out.String))
+	}
+	
+	// Should still contain replacements within the truncated portion
+	if !strings.Contains(out.String, "REPLACED") {
+		t.Fatalf("replacements not applied to truncated input")
+	}
+}
+
+func TestMultiRegexpFilterOverlappingPatterns(t *testing.T) {
+	f := MultiRegexpFilter{
+		Operations: []regexpFilterOperation{
+			{RawRegexp: `secret.*password`, Value: "SENSITIVE"},
+			{RawRegexp: `password`, Value: "HIDDEN"},
+		},
+	}
+	err := f.Provision(caddy.Context{})
+	if err != nil {
+		t.Fatalf("unexpected error provisioning: %v", err)
+	}
+
+	// The first pattern should match and replace the entire "secret...password" portion
+	// Then the second pattern should not find "password" anymore since it was already replaced
+	out := f.Filter(zapcore.Field{String: "my-secret-data-password-end"})
+	expected := "my-SENSITIVE-end"
+	if out.String != expected {
+		t.Fatalf("field has not been filtered correctly: got %s, expected %s", out.String, expected)
+	}
+}