diff --git a/docs/PRINCIPLES.md b/docs/PRINCIPLES.md
index 06fdeb6..9376b4f 100644
--- a/docs/PRINCIPLES.md
+++ b/docs/PRINCIPLES.md
@@ -71,9 +71,15 @@ a **single portable artifact** you can move between machines and sessions. Large
 are fine — Smocker handles them. ([#161])
 
 ### 3.4 Matching is faithful to real HTTP, not lenient
-- Header and query-parameter matching is **case-sensitive by design**. Real servers in the
-  wild are case-sensitive (e.g. AWS API Gateway), and being lenient would hide real bugs in
-  the system under test. ([#179])
+- **Header names** are matched **case-insensitively** (RFC 7230 §3.2: header field names are
+  case-insensitive), so a mock declaring `content-type` matches a request's `Content-Type`.
+  **Header values** and **query-parameter names** stay **case-sensitive by design**: real
+  servers are case-sensitive there (e.g. AWS API Gateway), and being lenient would hide real
+  bugs in the system under test. ([#179], [#281])
+- Smocker never rewrites the casing it is given: response headers are returned with the exact
+  case the mock declares (or the upstream sends, for proxies). Note that Go's `net/http`
+  canonicalizes header names when it parses an incoming request or an upstream proxy response,
+  so those reach Smocker already canonicalized regardless.
 - The default matcher is `ShouldEqual`; a bare string is shorthand for it. The matcher set
   (`ShouldMatch`, `ShouldContainSubstring`, `ShouldEqualJSON`, `ShouldNotBeEmpty`, …) is the
   vocabulary — prefer extending existing semantics over inventing parallel ones.
@@ -166,6 +172,7 @@ These are recognized gaps, not oversights — worth improving, but not regressio
 [#161]: https://github.com/smocker-dev/smocker/issues/161
 [#162]: https://github.com/smocker-dev/smocker/issues/162
 [#179]: https://github.com/smocker-dev/smocker/issues/179
+[#281]: https://github.com/smocker-dev/smocker/issues/281
 [#219]: https://github.com/smocker-dev/smocker/issues/219
 [#231]: https://github.com/smocker-dev/smocker/issues/231
 [#266]: https://github.com/smocker-dev/smocker/issues/266
diff --git a/server/types/matchers.go b/server/types/matchers.go
index 0db6ce1..ab742ea 100644
--- a/server/types/matchers.go
+++ b/server/types/matchers.go
@@ -249,6 +249,22 @@ func (mmm MultiMapMatcher) Match(values map[string][]string) bool {
 	return true
 }
 
+// MatchHeaders is like Match but resolves header names case-insensitively (RFC 7230 §3.2: header
+// field names are case-insensitive), so a mock declaring "content-type" matches a request's
+// "Content-Type". Header *values* are still matched exactly. The declared casing is never altered —
+// http.Header.Values only canonicalizes the key it looks up with, not the stored keys.
+func (mmm MultiMapMatcher) MatchHeaders(headers http.Header) bool {
+	if len(mmm) > len(headers) {
+		return false
+	}
+	for key, matcherValue := range mmm {
+		if value := headers.Values(key); len(value) == 0 || !matcherValue.Match(value) {
+			return false
+		}
+	}
+	return true
+}
+
 type BodyMatcher struct {
 	bodyString *StringMatcher
 	bodyJson   map[string]StringMatcher
diff --git a/server/types/matchers_test.go b/server/types/matchers_test.go
index c05352b..c6c4f34 100644
--- a/server/types/matchers_test.go
+++ b/server/types/matchers_test.go
@@ -2,12 +2,52 @@ package types
 
 import (
 	"encoding/json"
+	"net/http"
 	"reflect"
 	"testing"
 
 	"gopkg.in/yaml.v3"
 )
 
+func mapMatcher(t *testing.T, y string) MultiMapMatcher {
+	t.Helper()
+	var mmm MultiMapMatcher
+	if err := yaml.Unmarshal([]byte(y), &mmm); err != nil {
+		t.Fatalf("invalid matcher yaml: %v", err)
+	}
+	return mmm
+}
+
+// TestMatchHeadersCaseInsensitive covers #281: header *names* match case-insensitively (RFC 7230),
+// while header *values* — and query-parameter names via Match — stay case-sensitive.
+func TestMatchHeadersCaseInsensitive(t *testing.T) {
+	// A mock declaring a lowercase name matches the canonical request header, and vice versa.
+	req := http.Header{}
+	req.Set("Content-Type", "application/json") // net/http canonicalizes incoming names
+
+	if !mapMatcher(t, "content-type: application/json").MatchHeaders(req) {
+		t.Error(`"content-type" should match request header "Content-Type"`)
+	}
+	if !mapMatcher(t, "Content-Type: application/json").MatchHeaders(req) {
+		t.Error(`"Content-Type" should match request header "Content-Type"`)
+	}
+
+	// Header values remain case-sensitive.
+	if mapMatcher(t, "Content-Type: application/json").MatchHeaders(http.Header{"Content-Type": {"Application/JSON"}}) {
+		t.Error("header values must stay case-sensitive")
+	}
+
+	// A missing header still fails to match.
+	if mapMatcher(t, "X-Absent: x").MatchHeaders(req) {
+		t.Error("a header absent from the request must not match")
+	}
+
+	// Query-parameter matching (Match) stays case-sensitive on names.
+	if mapMatcher(t, "Token: abc").Match(map[string][]string{"token": {"abc"}}) {
+		t.Error("query-parameter names must stay case-sensitive")
+	}
+}
+
 func TestStringMatcherJSON(t *testing.T) {
 	test := `"test"`
 	serialized := `{"matcher":"ShouldEqual","value":"test"}`
diff --git a/server/types/mock.go b/server/types/mock.go
index 93eb784..d8cf00c 100644
--- a/server/types/mock.go
+++ b/server/types/mock.go
@@ -120,7 +120,7 @@ func (mr MockRequest) Match(req Request) bool {
 		slog.Debug("Path did not match")
 		return false
 	}
-	matchHeaders := mr.Headers == nil || mr.Headers.Match(req.Headers)
+	matchHeaders := mr.Headers == nil || mr.Headers.MatchHeaders(req.Headers)
 	if !matchHeaders {
 		slog.Debug("Headers did not match")
 		return false