diff --git a/spring-web/src/main/java/org/springframework/http/server/ServletRequestHeadersAdapter.java b/spring-web/src/main/java/org/springframework/http/server/ServletRequestHeadersAdapter.java
new file mode 100644
index 00000000000..7c1b49bf678
--- /dev/null
+++ b/spring-web/src/main/java/org/springframework/http/server/ServletRequestHeadersAdapter.java
@@ -0,0 +1,527 @@
+/*
+ * Copyright 2002-present the original author or authors.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.http.server;
+
+import java.util.AbstractSet;
+import java.util.ArrayList;
+import java.util.Collection;
+import java.util.Enumeration;
+import java.util.Iterator;
+import java.util.LinkedHashMap;
+import java.util.LinkedHashSet;
+import java.util.List;
+import java.util.Locale;
+import java.util.Map;
+import java.util.Set;
+
+import jakarta.servlet.http.HttpServletRequest;
+import org.jspecify.annotations.Nullable;
+
+import org.springframework.http.HttpHeaders;
+import org.springframework.util.CollectionUtils;
+import org.springframework.util.LinkedCaseInsensitiveMap;
+import org.springframework.util.MultiValueMap;
+
+/**
+ * {@code MultiValueMap} implementation for wrapping Servlet request headers.
+ *
+ * @author Rossen Stoyanchev
+ * @since 7.0.5
+ */
+final class ServletRequestHeadersAdapter implements MultiValueMap<String, String> {
+
+	private final HttpServletRequest request;
+
+
+	ServletRequestHeadersAdapter(HttpServletRequest request) {
+		this.request = request;
+	}
+
+
+	@Override
+	public @Nullable String getFirst(String key) {
+		return this.request.getHeader(key);
+	}
+
+	@Override
+	public void add(String key, @Nullable String value) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public void addAll(String key, List<? extends String> values) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public void addAll(MultiValueMap<String, String> map) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public void set(String key, @Nullable String value) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public void setAll(Map<String, String> map) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public Map<String, String> toSingleValueMap() {
+		Map<String, String> map = new LinkedHashMap<>();
+		Enumeration<String> names = this.request.getHeaderNames();
+		while (names.hasMoreElements()) {
+			String name = names.nextElement();
+			map.put(name, this.request.getHeader(name));
+		}
+		return map;
+	}
+
+	@Override
+	public int size() {
+		Enumeration<String> names = this.request.getHeaderNames();
+		Set<String> set = new LinkedHashSet<>();
+		while (names.hasMoreElements()) {
+			set.add(names.nextElement().toLowerCase(Locale.ROOT));
+		}
+		return set.size();
+	}
+
+	@Override
+	public boolean isEmpty() {
+		return !this.request.getHeaderNames().hasMoreElements();
+	}
+
+	@Override
+	public boolean containsKey(Object key) {
+		if (key instanceof String headerName) {
+			Enumeration<String> names = this.request.getHeaderNames();
+			while (names.hasMoreElements()) {
+				if (headerName.equalsIgnoreCase(names.nextElement())) {
+					return true;
+				}
+			}
+		}
+		return false;
+	}
+
+	@Override
+	public boolean containsValue(Object rawValue) {
+		if (rawValue instanceof String text) {
+			Enumeration<String> names = this.request.getHeaderNames();
+			while (names.hasMoreElements()) {
+				Enumeration<String> values = this.request.getHeaders(names.nextElement());
+				while (values.hasMoreElements()) {
+					if (text.equals(values.nextElement())) {
+						return true;
+					}
+				}
+			}
+		}
+		return false;
+	}
+
+	@Override
+	public @Nullable List<String> get(Object key) {
+		if (key instanceof String headerName) {
+			Enumeration<String> values = this.request.getHeaders(headerName);
+			if (values.hasMoreElements()) {
+				List<String> result = new ArrayList<>();
+				while (values.hasMoreElements()) {
+					result.add(values.nextElement());
+				}
+				return result;
+			}
+		}
+		return null;
+	}
+
+	@Override
+	public @Nullable List<String> put(String key, List<String> value) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public @Nullable List<String> remove(Object key) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public void putAll(Map<? extends String, ? extends List<String>> map) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public void clear() {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public Set<String> keySet() {
+		Set<String> set = new LinkedHashSet<>();
+		Enumeration<String> names = this.request.getHeaderNames();
+		while (names.hasMoreElements()) {
+			set.add(names.nextElement());
+		}
+		return set;
+	}
+
+	@Override
+	public Collection<List<String>> values() {
+		List<List<String>> allValues = new ArrayList<>();
+		Enumeration<String> names = this.request.getHeaderNames();
+		while (names.hasMoreElements()) {
+			String name = names.nextElement();
+			List<String> currentValues = new ArrayList<>();
+			Enumeration<String> values = this.request.getHeaders(name);
+			while (values.hasMoreElements()) {
+				currentValues.add(values.nextElement());
+			}
+			allValues.add(currentValues);
+		}
+		return allValues;
+	}
+
+	@Override
+	public Set<Entry<String, List<String>>> entrySet() {
+		return new AbstractSet<>() {
+			@Override
+			public Iterator<Entry<String, List<String>>> iterator() {
+				return new EntryIterator();
+			}
+
+			@Override
+			public int size() {
+				return ServletRequestHeadersAdapter.this.size();
+			}
+		};
+	}
+
+
+	@Override
+	public int hashCode() {
+		return Map.copyOf(this).hashCode();
+	}
+
+	@Override
+	public boolean equals(@Nullable Object other) {
+		return (this == other ||
+				(other instanceof MultiValueMap<?,?> that && Map.copyOf(this).equals(that)));
+	}
+
+	@Override
+	public String toString() {
+		return HttpHeaders.formatHeaders(this);
+	}
+
+
+	/**
+	 * Apply a wrapper that allows headers to be set or added, and treats those
+	 * as overrides to the headers in the given MultiValueMap.
+	 * @param headers the headers map to wrap
+	 * @return the wrapper instance
+	 */
+	public static MultiValueMap<String, String> overrideHeadersWrapper(MultiValueMap<String, String> headers) {
+		return new OverrideHeaderWrapper(headers);
+	}
+
+
+	private class EntryIterator implements Iterator<Entry<String, List<String>>> {
+
+		private final Iterator<String> names = ServletRequestHeadersAdapter.this.keySet().iterator();
+
+		@Override
+		public boolean hasNext() {
+			return this.names.hasNext();
+		}
+
+		@Override
+		public Entry<String, List<String>> next() {
+			return new HeaderEntry(this.names.next());
+		}
+	}
+
+
+	private final class HeaderEntry implements Entry<String, List<String>> {
+
+		private final String key;
+
+		HeaderEntry(String key) {
+			this.key = key;
+		}
+
+		@Override
+		public String getKey() {
+			return this.key;
+		}
+
+		@Override
+		public @Nullable List<String> getValue() {
+			return get(this.key);
+		}
+
+		@Override
+		public @Nullable List<String> setValue(List<String> value) {
+			List<String> previous = getValue();
+			remove(this.key);
+			addAll(this.key, value);
+			return previous;
+		}
+	}
+
+
+	/**
+	 * Wrapper that supports optional override values.
+	 */
+	private static class OverrideHeaderWrapper implements MultiValueMap<String, String> {
+
+		private final MultiValueMap<String, String> delegate;
+
+		private @Nullable MultiValueMap<String, String> overrideHeaders;
+
+		OverrideHeaderWrapper(MultiValueMap<String, String> delegate) {
+			this.delegate = delegate;
+		}
+
+		@Override
+		public @Nullable String getFirst(String key) {
+			String value = (this.overrideHeaders != null ? this.overrideHeaders.getFirst(key) : null);
+			return (value != null ? value : this.delegate.getFirst(key));
+		}
+
+		@Override
+		public void add(String key, @Nullable String value) {
+			initOverrideHeaders().add(key, value);
+		}
+
+		@Override
+		public void addAll(String key, List<? extends String> values) {
+			initOverrideHeaders().addAll(key, values);
+		}
+
+		@Override
+		public void addAll(MultiValueMap<String, String> map) {
+			initOverrideHeaders().addAll(map);
+		}
+
+		@Override
+		public void set(String key, @Nullable String value) {
+			initOverrideHeaders().set(key, value);
+		}
+
+		@Override
+		public void setAll(Map<String, String> map) {
+			initOverrideHeaders().setAll(map);
+		}
+
+		@Override
+		public Map<String, String> toSingleValueMap() {
+			Map<String, String> map = this.delegate.toSingleValueMap();
+			if (this.overrideHeaders != null) {
+				this.overrideHeaders.forEach((key, values) -> map.put(key, values.get(0)));
+			}
+			return map;
+		}
+
+		@Override
+		public int size() {
+			if (this.overrideHeaders == null) {
+				return this.delegate.size();
+			}
+			Set<String> set = new LinkedHashSet<>();
+			for (String name : this.delegate.keySet()) {
+				set.add(name.toLowerCase(Locale.ROOT));
+			}
+			this.overrideHeaders.keySet().forEach(key -> set.add(key.toLowerCase(Locale.ROOT)));
+			return set.size();
+		}
+
+		@Override
+		public boolean isEmpty() {
+			return (this.delegate.isEmpty() && (this.overrideHeaders == null || this.overrideHeaders.isEmpty()));
+		}
+
+		@Override
+		public boolean containsKey(Object key) {
+			if (key instanceof String headerName) {
+				if (this.delegate.containsKey(headerName)) {
+					return true;
+				}
+				if (this.overrideHeaders != null) {
+					return this.overrideHeaders.containsKey(headerName);
+				}
+			}
+			return false;
+		}
+
+		@Override
+		public boolean containsValue(Object rawValue) {
+			if (rawValue instanceof String text) {
+				if (this.delegate.containsValue(text)) {
+					return true;
+				}
+				if (this.overrideHeaders != null) {
+					return this.overrideHeaders.containsValue(rawValue);
+				}
+			}
+			return false;
+		}
+
+		@Override
+		public @Nullable List<String> get(Object key) {
+			if (key instanceof String headerName) {
+				if (this.overrideHeaders != null) {
+					List<String> values = this.overrideHeaders.get(headerName);
+					if (values != null) {
+						return values;
+					}
+				}
+				return this.delegate.get(headerName);
+			}
+			return null;
+		}
+
+		@Override
+		public @Nullable List<String> put(String key, List<String> value) {
+			return initOverrideHeaders().put(key, value);
+		}
+
+		@Override
+		public @Nullable List<String> remove(Object key) {
+			return initOverrideHeaders().remove(key);
+		}
+
+		@Override
+		public void putAll(Map<? extends String, ? extends List<String>> map) {
+			initOverrideHeaders().putAll(map);
+		}
+
+		@Override
+		public void clear() {
+			initOverrideHeaders().clear();
+		}
+
+		@Override
+		public Set<String> keySet() {
+			Set<String> set = this.delegate.keySet();
+			if (this.overrideHeaders != null) {
+				set.addAll(this.overrideHeaders.keySet());
+			}
+			return set;
+		}
+
+		@Override
+		public Collection<List<String>> values() {
+			List<List<String>> allValues = new ArrayList<>();
+			for (String name : keySet()) {
+				if (this.overrideHeaders != null && this.overrideHeaders.containsKey(name)) {
+					allValues.add(this.overrideHeaders.get(name));
+				}
+				else {
+					allValues.add(this.delegate.get(name));
+				}
+			}
+			return allValues;
+		}
+
+		@Override
+		public Set<Entry<String, List<String>>> entrySet() {
+			return new AbstractSet<>() {
+				@Override
+				public Iterator<Entry<String, List<String>>> iterator() {
+					return new OverrideHeaderWrapper.EntryIterator();
+				}
+
+				@Override
+				public int size() {
+					return OverrideHeaderWrapper.this.size();
+				}
+			};
+		}
+
+		private MultiValueMap<String, String> initOverrideHeaders() {
+			if (this.overrideHeaders == null) {
+				this.overrideHeaders = CollectionUtils.toMultiValueMap(new LinkedCaseInsensitiveMap<>(8, Locale.ROOT));
+			}
+			return this.overrideHeaders;
+		}
+
+
+		@Override
+		public int hashCode() {
+			return Map.copyOf(this).hashCode();
+		}
+
+		@Override
+		public boolean equals(@Nullable Object other) {
+			return (this == other ||
+					(other instanceof MultiValueMap<?,?> that && Map.copyOf(this).equals(that)));
+		}
+
+		@Override
+		public String toString() {
+			return HttpHeaders.formatHeaders(this);
+		}
+
+
+		private class EntryIterator implements Iterator<Entry<String, List<String>>> {
+
+			private final Iterator<String> names = OverrideHeaderWrapper.this.keySet().iterator();
+
+			@Override
+			public boolean hasNext() {
+				return this.names.hasNext();
+			}
+
+			@Override
+			public Entry<String, List<String>> next() {
+				return new OverrideHeaderWrapper.HeaderEntry(this.names.next());
+			}
+		}
+
+
+		private final class HeaderEntry implements Entry<String, List<String>> {
+
+			private final String key;
+
+			HeaderEntry(String key) {
+				this.key = key;
+			}
+
+			@Override
+			public String getKey() {
+				return this.key;
+			}
+
+			@Override
+			public @Nullable List<String> getValue() {
+				return get(this.key);
+			}
+
+			@Override
+			public @Nullable List<String> setValue(List<String> value) {
+				List<String> previous = getValue();
+				remove(this.key);
+				addAll(this.key, value);
+				return previous;
+			}
+		}
+	}
+
+}
diff --git a/spring-web/src/main/java/org/springframework/http/server/ServletResponseHeadersAdapter.java b/spring-web/src/main/java/org/springframework/http/server/ServletResponseHeadersAdapter.java
new file mode 100644
index 00000000000..d9456bd415e
--- /dev/null
+++ b/spring-web/src/main/java/org/springframework/http/server/ServletResponseHeadersAdapter.java
@@ -0,0 +1,269 @@
+/*
+ * Copyright 2002-present the original author or authors.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.http.server;
+
+import java.util.AbstractSet;
+import java.util.ArrayList;
+import java.util.Collection;
+import java.util.Collections;
+import java.util.Iterator;
+import java.util.LinkedHashMap;
+import java.util.LinkedHashSet;
+import java.util.List;
+import java.util.Map;
+import java.util.Set;
+
+import jakarta.servlet.http.HttpServletResponse;
+import org.jspecify.annotations.Nullable;
+
+import org.springframework.http.HttpHeaders;
+import org.springframework.util.MultiValueMap;
+
+/**
+ * {@code MultiValueMap} implementation for wrapping Servlet response headers.
+ *
+ * @author Rossen Stoyanchev
+ * @since 7.0.5
+ */
+class ServletResponseHeadersAdapter implements MultiValueMap<String, String> {
+
+	private final HttpServletResponse response;
+
+
+	ServletResponseHeadersAdapter(HttpServletResponse response) {
+		this.response = response;
+	}
+
+
+	@Override
+	public String getFirst(String key) {
+		return this.response.getHeader(key);
+	}
+
+	@Override
+	public void add(String key, @Nullable String value) {
+		this.response.addHeader(key, value);
+	}
+
+	@Override
+	public void addAll(String key, List<? extends String> values) {
+		values.forEach(value -> this.response.addHeader(key, value));
+	}
+
+	@Override
+	public void addAll(MultiValueMap<String, String> map) {
+		for (Entry<String, List<String>> entry : map.entrySet()) {
+			for (String value : entry.getValue()) {
+				this.response.addHeader(entry.getKey(), value);
+			}
+		}
+	}
+
+	@Override
+	public void set(String key, @Nullable String value) {
+		this.response.setHeader(key, value);
+	}
+
+	@Override
+	public void setAll(Map<String, String> map) {
+		for (Entry<String, String> entry : map.entrySet()) {
+			this.response.setHeader(entry.getKey(), entry.getValue());
+		}
+	}
+
+	@Override
+	public Map<String, String> toSingleValueMap() {
+		Map<String, String> map = new LinkedHashMap<>();
+		Collection<String> names = this.response.getHeaderNames();
+		for (String name : names) {
+			map.put(name, this.response.getHeader(name));
+		}
+		return map;
+	}
+
+	@Override
+	public int size() {
+		return this.response.getHeaderNames().size();
+	}
+
+	@Override
+	public boolean isEmpty() {
+		return this.response.getHeaderNames().isEmpty();
+	}
+
+	@Override
+	public boolean containsKey(Object key) {
+		if (key instanceof String headerName) {
+			return this.response.containsHeader(headerName);
+		}
+		return false;
+	}
+
+	@Override
+	public boolean containsValue(Object rawValue) {
+		if (rawValue instanceof String text) {
+			for (String name : this.response.getHeaderNames()) {
+				Collection<String> values = this.response.getHeaders(name);
+				for (String value : values) {
+					if (text.equals(value)) {
+						return true;
+					}
+				}
+			}
+		}
+		return false;
+	}
+
+	@Override
+	public @Nullable List<String> get(Object key) {
+		if (key instanceof String headerName) {
+			Collection<String> values = this.response.getHeaders(headerName);
+			if (!values.isEmpty()) {
+				return (values instanceof List ? (List<String>) values : new ArrayList<>(values));
+			}
+			return (this.response.containsHeader(headerName) ? Collections.emptyList() : null);
+		}
+		return null;
+	}
+
+	@Override
+	public @Nullable List<String> put(String key, List<String> values) {
+		List<String> previous = remove(key);
+		for (String value : values) {
+			this.response.addHeader(key, value);
+		}
+		return previous;
+	}
+
+	@Override
+	public @Nullable List<String> remove(Object key) {
+		if (key instanceof String headerName) {
+			Collection<String> previous = this.response.getHeaders(headerName);
+			if (previous != null) {
+				this.response.setHeader(headerName, null);
+			}
+			return (previous != null ? new ArrayList<>(previous) : null);
+		}
+		return null;
+	}
+
+	@Override
+	public void putAll(Map<? extends String, ? extends List<String>> map) {
+		for (Entry<? extends String, ? extends List<String>> entry : map.entrySet()) {
+			this.response.setHeader(entry.getKey(), null);
+			for (String value : entry.getValue()) {
+				this.response.addHeader(entry.getKey(), value);
+			}
+		}
+	}
+
+	@Override
+	public void clear() {
+		for (String headerName : this.response.getHeaderNames()) {
+			this.response.setHeader(headerName, null);
+		}
+	}
+
+	@Override
+	public Set<String> keySet() {
+		return new LinkedHashSet<>(this.response.getHeaderNames());
+	}
+
+	@Override
+	public Collection<List<String>> values() {
+		List<List<String>> allValues = new ArrayList<>();
+		for (String name : this.response.getHeaderNames()) {
+			allValues.add(new ArrayList<>(this.response.getHeaders(name)));
+		}
+		return allValues;
+	}
+
+	@Override
+	public Set<Entry<String, List<String>>> entrySet() {
+		return new AbstractSet<>() {
+			@Override
+			public Iterator<Entry<String, List<String>>> iterator() {
+				return new EntryIterator();
+			}
+
+			@Override
+			public int size() {
+				return ServletResponseHeadersAdapter.this.size();
+			}
+		};
+	}
+
+
+	@Override
+	public int hashCode() {
+		return Map.copyOf(this).hashCode();
+	}
+
+	@Override
+	public boolean equals(@Nullable Object other) {
+		return (this == other ||
+				(other instanceof MultiValueMap<?,?> that && Map.copyOf(this).equals(that)));
+	}
+
+	@Override
+	public String toString() {
+		return HttpHeaders.formatHeaders(this);
+	}
+
+
+	private class EntryIterator implements Iterator<Entry<String, List<String>>> {
+
+		private final Iterator<String> names =
+				ServletResponseHeadersAdapter.this.response.getHeaderNames().iterator();
+
+		@Override
+		public boolean hasNext() {
+			return this.names.hasNext();
+		}
+
+		@Override
+		public Entry<String, List<String>> next() {
+			return new HeaderEntry(this.names.next());
+		}
+	}
+
+
+	private final class HeaderEntry implements Entry<String, List<String>> {
+
+		private final String key;
+
+		HeaderEntry(String key) {
+			this.key = key;
+		}
+
+		@Override
+		public String getKey() {
+			return this.key;
+		}
+
+		@Override
+		public @Nullable List<String> getValue() {
+			return ServletResponseHeadersAdapter.this.get(this.key);
+		}
+
+		@Override
+		public @Nullable List<String> setValue(List<String> values) {
+			return ServletResponseHeadersAdapter.this.put(this.key, values);
+		}
+	}
+
+}
diff --git a/spring-web/src/main/java/org/springframework/http/server/ServletServerHttpRequest.java b/spring-web/src/main/java/org/springframework/http/server/ServletServerHttpRequest.java
index f6b99c94bb2..a2724f51b06 100644
--- a/spring-web/src/main/java/org/springframework/http/server/ServletServerHttpRequest.java
+++ b/spring-web/src/main/java/org/springframework/http/server/ServletServerHttpRequest.java
@@ -22,6 +22,7 @@ import java.io.IOException;
 import java.io.InputStream;
 import java.io.OutputStreamWriter;
 import java.io.Writer;
+import java.lang.reflect.Field;
 import java.net.InetSocketAddress;
 import java.net.URI;
 import java.net.URISyntaxException;
@@ -41,6 +42,9 @@ import java.util.Map;
 import java.util.Set;
 
 import jakarta.servlet.http.HttpServletRequest;
+import jakarta.servlet.http.HttpServletRequestWrapper;
+import org.apache.catalina.connector.RequestFacade;
+import org.apache.coyote.Request;
 import org.jspecify.annotations.Nullable;
 
 import org.springframework.http.HttpHeaders;
@@ -48,7 +52,10 @@ import org.springframework.http.HttpMethod;
 import org.springframework.http.InvalidMediaTypeException;
 import org.springframework.http.MediaType;
 import org.springframework.util.Assert;
+import org.springframework.util.ClassUtils;
 import org.springframework.util.LinkedCaseInsensitiveMap;
+import org.springframework.util.MultiValueMap;
+import org.springframework.util.ReflectionUtils;
 import org.springframework.util.StringUtils;
 
 /**
@@ -63,6 +70,9 @@ public class ServletServerHttpRequest implements ServerHttpRequest {
 
 	protected static final Charset FORM_CHARSET = StandardCharsets.UTF_8;
 
+	private static final boolean TOMCAT_PRESENT = ClassUtils.isPresent(
+			"org.apache.tomcat.util.http.MimeHeaders", ServletServerHttpRequest.class.getClassLoader());
+
 
 	private final HttpServletRequest servletRequest;
 
@@ -156,16 +166,8 @@ public class ServletServerHttpRequest implements ServerHttpRequest {
 	@Override
 	public HttpHeaders getHeaders() {
 		if (this.headers == null) {
-			this.headers = new HttpHeaders();
-
-			for (Enumeration<?> names = this.servletRequest.getHeaderNames(); names.hasMoreElements();) {
-				String headerName = (String) names.nextElement();
-				for (Enumeration<?> headerValues = this.servletRequest.getHeaders(headerName);
-						headerValues.hasMoreElements();) {
-					String headerValue = (String) headerValues.nextElement();
-					this.headers.add(headerName, headerValue);
-				}
-			}
+			MultiValueMap<String, String> headersAdapter = initHeadersMultiValueMap();
+			this.headers = new HttpHeaders(headersAdapter);
 
 			// HttpServletRequest exposes some headers as properties:
 			// we should include those if not already present
@@ -203,10 +205,21 @@ public class ServletServerHttpRequest implements ServerHttpRequest {
 				}
 			}
 		}
-
 		return this.headers;
 	}
 
+	private MultiValueMap<String, String> initHeadersMultiValueMap() {
+		MultiValueMap<String, String> nativeHeaders = null;
+		if (TOMCAT_PRESENT) {
+			nativeHeaders = TomcatInitializer.createTomcatHttpHeaders(this.servletRequest);
+		}
+		if (nativeHeaders == null) {
+			nativeHeaders = new ServletRequestHeadersAdapter(this.servletRequest);
+		}
+		return ServletRequestHeadersAdapter.overrideHeadersWrapper(nativeHeaders);
+	}
+
+
 	@Override
 	public @Nullable Principal getPrincipal() {
 		return this.servletRequest.getUserPrincipal();
@@ -317,6 +330,41 @@ public class ServletServerHttpRequest implements ServerHttpRequest {
 	}
 
 
+	private static final class TomcatInitializer {
+
+		private static final Field COYOTE_REQUEST_FIELD;
+
+		static {
+			Field field = ReflectionUtils.findField(RequestFacade.class, "request");
+			Assert.state(field != null, "Incompatible Tomcat implementation");
+			ReflectionUtils.makeAccessible(field);
+			COYOTE_REQUEST_FIELD = field;
+		}
+
+		public static @Nullable MultiValueMap<String, String> createTomcatHttpHeaders(HttpServletRequest servletRequest) {
+			RequestFacade requestFacade = getRequestFacade(servletRequest);
+			if (requestFacade == null) {
+				return null;
+			}
+			Object field = ReflectionUtils.getField(COYOTE_REQUEST_FIELD, requestFacade);
+			Assert.state(field != null, "No Tomcat connector request");
+			Request coyoteRequest = ((org.apache.catalina.connector.Request) field).getCoyoteRequest();
+			return new TomcatHeadersAdapter(coyoteRequest.getMimeHeaders());
+		}
+
+		private static @Nullable RequestFacade getRequestFacade(HttpServletRequest request) {
+			if (request instanceof RequestFacade facade) {
+				return facade;
+			}
+			else if (request instanceof HttpServletRequestWrapper wrapper) {
+				HttpServletRequest wrappedRequest = (HttpServletRequest) wrapper.getRequest();
+				return getRequestFacade(wrappedRequest);
+			}
+			return null;
+		}
+	}
+
+
 	private final class AttributesMap extends AbstractMap<String, Object> {
 
 		private @Nullable transient Set<String> keySet;
diff --git a/spring-web/src/main/java/org/springframework/http/server/ServletServerHttpResponse.java b/spring-web/src/main/java/org/springframework/http/server/ServletServerHttpResponse.java
index b1e0a13e6b6..843f603de3c 100644
--- a/spring-web/src/main/java/org/springframework/http/server/ServletServerHttpResponse.java
+++ b/spring-web/src/main/java/org/springframework/http/server/ServletServerHttpResponse.java
@@ -18,19 +18,13 @@ package org.springframework.http.server;
 
 import java.io.IOException;
 import java.io.OutputStream;
-import java.util.ArrayList;
-import java.util.Collection;
-import java.util.Collections;
-import java.util.List;
 
 import jakarta.servlet.http.HttpServletResponse;
 import org.jspecify.annotations.Nullable;
 
 import org.springframework.http.HttpHeaders;
 import org.springframework.http.HttpStatusCode;
-import org.springframework.http.MediaType;
 import org.springframework.util.Assert;
-import org.springframework.util.CollectionUtils;
 
 /**
  * {@link ServerHttpResponse} implementation that is based on a {@link HttpServletResponse}.
@@ -59,7 +53,7 @@ public class ServletServerHttpResponse implements ServerHttpResponse {
 	public ServletServerHttpResponse(HttpServletResponse servletResponse) {
 		Assert.notNull(servletResponse, "HttpServletResponse must not be null");
 		this.servletResponse = servletResponse;
-		this.headers = new ServletResponseHttpHeaders();
+		this.headers = new HttpHeaders(new ServletResponseHeadersAdapter(servletResponse));
 	}
 
 
@@ -112,92 +106,8 @@ public class ServletServerHttpResponse implements ServerHttpResponse {
 
 	private void writeHeaders() {
 		if (!this.headersWritten) {
-			getHeaders().forEach((headerName, headerValues) -> {
-				for (String headerValue : headerValues) {
-					this.servletResponse.addHeader(headerName, headerValue);
-				}
-			});
-			// HttpServletResponse exposes some headers as properties: we should include those if not already present
-			MediaType contentTypeHeader = this.headers.getContentType();
-			if (this.servletResponse.getContentType() == null && contentTypeHeader != null) {
-				this.servletResponse.setContentType(contentTypeHeader.toString());
-			}
-			if (this.servletResponse.getCharacterEncoding() == null && contentTypeHeader != null &&
-					contentTypeHeader.getCharset() != null) {
-				this.servletResponse.setCharacterEncoding(contentTypeHeader.getCharset().name());
-			}
-			long contentLength = getHeaders().getContentLength();
-			if (contentLength != -1) {
-				this.servletResponse.setContentLengthLong(contentLength);
-			}
 			this.headersWritten = true;
 		}
 	}
 
-
-	/**
-	 * Extends HttpHeaders with the ability to look up headers already present in
-	 * the underlying HttpServletResponse.
-	 *
-	 * <p>The intent is merely to expose what is available through the HttpServletResponse
-	 * i.e. the ability to look up specific header values by name. All other
-	 * map-related operations (for example, iteration, removal, etc) apply only to values
-	 * added directly through HttpHeaders methods.
-	 *
-	 * @since 4.0.3
-	 */
-	private class ServletResponseHttpHeaders extends HttpHeaders {
-
-		private static final long serialVersionUID = 3410708522401046302L;
-
-		@Override
-		public boolean containsHeader(String key) {
-			return (super.containsHeader(key) || (get(key) != null));
-		}
-
-		@Override
-		public @Nullable String getFirst(String headerName) {
-			if (headerName.equalsIgnoreCase(CONTENT_TYPE)) {
-				// Content-Type is written as an override so check super first
-				String value = super.getFirst(headerName);
-				return (value != null ? value : servletResponse.getContentType());
-			}
-			else {
-				String value = servletResponse.getHeader(headerName);
-				return (value != null ? value : super.getFirst(headerName));
-			}
-		}
-
-		@Override
-		public @Nullable List<String> get(String headerName) {
-			if (headerName.equalsIgnoreCase(CONTENT_TYPE)) {
-				// Content-Type is written as an override so don't merge
-				String value = getFirst(headerName);
-				return (value != null ? Collections.singletonList(value) : null);
-			}
-
-			Collection<String> values1 = servletResponse.getHeaders(headerName);
-			if (headersWritten) {
-				return new ArrayList<>(values1);
-			}
-			boolean isEmpty1 = CollectionUtils.isEmpty(values1);
-
-			List<String> values2 = super.get(headerName);
-			boolean isEmpty2 = CollectionUtils.isEmpty(values2);
-
-			if (isEmpty1 && isEmpty2) {
-				return null;
-			}
-
-			List<String> values = new ArrayList<>();
-			if (!isEmpty1) {
-				values.addAll(values1);
-			}
-			if (!isEmpty2) {
-				values.addAll(values2);
-			}
-			return values;
-		}
-	}
-
 }
diff --git a/spring-webmvc/src/main/java/org/springframework/web/servlet/mvc/method/annotation/HttpEntityMethodProcessor.java b/spring-webmvc/src/main/java/org/springframework/web/servlet/mvc/method/annotation/HttpEntityMethodProcessor.java
index 0bf8037b2e0..ba6a0388687 100644
--- a/spring-webmvc/src/main/java/org/springframework/web/servlet/mvc/method/annotation/HttpEntityMethodProcessor.java
+++ b/spring-webmvc/src/main/java/org/springframework/web/servlet/mvc/method/annotation/HttpEntityMethodProcessor.java
@@ -229,7 +229,7 @@ public class HttpEntityMethodProcessor extends AbstractMessageConverterMethodPro
 				if (HttpHeaders.VARY.equals(key) && outputHeaders.containsHeader(HttpHeaders.VARY)) {
 					List<String> values = getVaryRequestHeadersToAdd(outputHeaders, entityHeaders);
 					if (!values.isEmpty()) {
-						outputHeaders.setVary(values);
+						outputHeaders.addAll(HttpHeaders.VARY, values);
 					}
 				}
 				else {
diff --git a/spring-webmvc/src/test/java/org/springframework/web/servlet/mvc/method/annotation/ResponseBodyEmitterReturnValueHandlerTests.java b/spring-webmvc/src/test/java/org/springframework/web/servlet/mvc/method/annotation/ResponseBodyEmitterReturnValueHandlerTests.java
index 2abfe70f767..c8fbbd59bda 100644
--- a/spring-webmvc/src/test/java/org/springframework/web/servlet/mvc/method/annotation/ResponseBodyEmitterReturnValueHandlerTests.java
+++ b/spring-webmvc/src/test/java/org/springframework/web/servlet/mvc/method/annotation/ResponseBodyEmitterReturnValueHandlerTests.java
@@ -288,7 +288,7 @@ class ResponseBodyEmitterReturnValueHandlerTests {
 
 		WebAsyncManager asyncManager = WebAsyncUtils.getAsyncManager(this.webRequest);
 		assertThat(asyncManager.getConcurrentResult()).isSameAs(ex);
-		assertThat(this.response.getContentType()).isNull();
+		assertThat(this.response.getContentType()).isEqualTo(MediaType.TEXT_EVENT_STREAM_VALUE);
 	}
 
 	@Test