diff --git a/dd-java-agent/agent-bootstrap/src/main/java/datadog/trace/bootstrap/instrumentation/dbm/SharedDBCommenter.java b/dd-java-agent/agent-bootstrap/src/main/java/datadog/trace/bootstrap/instrumentation/dbm/SharedDBCommenter.java
index 83604a017bd..1df7f063493 100644
--- a/dd-java-agent/agent-bootstrap/src/main/java/datadog/trace/bootstrap/instrumentation/dbm/SharedDBCommenter.java
+++ b/dd-java-agent/agent-bootstrap/src/main/java/datadog/trace/bootstrap/instrumentation/dbm/SharedDBCommenter.java
@@ -9,6 +9,7 @@
 import java.io.UnsupportedEncodingException;
 import java.net.URLEncoder;
 import java.nio.charset.StandardCharsets;
+import java.util.concurrent.ConcurrentHashMap;
 import org.slf4j.Logger;
 import org.slf4j.LoggerFactory;
 
@@ -32,6 +33,28 @@ public class SharedDBCommenter {
   private static final String TRACEPARENT = encode("traceparent");
   private static final String DD_SERVICE_HASH = encode("ddsh");
 
+  /**
+   * Cached static suffix: "dde='<env>',ddpv='<version>'" Computed lazily on first use
+   * since Config may not be available at class-load time.
+   */
+  private static volatile String cachedStaticSuffix;
+
+  /** Cached URL-encoded service name from Config. */
+  private static volatile String cachedEncodedServiceName;
+
+  /** The Config instance used to compute the cached values, for staleness detection. */
+  private static volatile Config cachedConfigInstance;
+
+  /**
+   * Cached per-connection prefix fragments keyed by (dbService, hostname, dbName). Each entry holds
+   * the pre-encoded "ddps='...',dddbs='...',ddh='...',dddb='...'" fragment, combining the static
+   * service name with per-connection values to preserve the correct field ordering.
+   */
+  private static final int MAX_CONNECTION_CACHE_SIZE = 256;
+
+  private static final ConcurrentHashMap<ConnectionKey, String> connectionPrefixCache =
+      new ConcurrentHashMap<>();
+
   // Used by SQLCommenter and MongoCommentInjector to avoid duplicate comment injection
   public static boolean containsTraceComment(String commentContent) {
     return commentContent.contains(PARENT_SERVICE + "=")
@@ -50,25 +73,111 @@ public static String buildComment(
       String dbService, String dbType, String hostname, String dbName, String traceParent) {
 
     Config config = Config.get();
-    StringBuilder sb = new StringBuilder();
 
-    int initSize = 0; // No initial content for pure comment
-    append(sb, PARENT_SERVICE, config.getServiceName(), initSize);
-    append(sb, DATABASE_SERVICE, dbService, initSize);
-    append(sb, DD_HOSTNAME, hostname, initSize);
-    append(sb, DD_DB_NAME, dbName, initSize);
-    append(sb, DD_PEER_SERVICE, getPeerService(), initSize);
-    append(sb, DD_ENV, config.getEnv(), initSize);
-    append(sb, DD_VERSION, config.getVersion(), initSize);
-    append(sb, TRACEPARENT, traceParent, initSize);
+    // Ensure static values are initialized
+    ensureStaticValuesInitialized(config);
+
+    // Get or compute the prefix: ddps='...',dddbs='...',ddh='...',dddb='...'
+    String prefix = getConnectionPrefix(dbService, hostname, dbName);
+
+    // Get the cached static suffix: dde='...',ddpv='...'
+    String suffix = cachedStaticSuffix;
 
-    if (config.isDbmInjectSqlBaseHash() && config.isExperimentalPropagateProcessTagsEnabled()) {
-      append(sb, DD_SERVICE_HASH, BaseHash.getBaseHashStr(), initSize);
+    // Dynamic values that change per-call
+    String peerService = getPeerService();
+    boolean injectBaseHash =
+        config.isDbmInjectSqlBaseHash() && config.isExperimentalPropagateProcessTagsEnabled();
+    String baseHash = injectBaseHash ? BaseHash.getBaseHashStr() : null;
+
+    // Estimate capacity
+    int capacity =
+        (prefix != null ? prefix.length() : 0)
+            + (suffix != null ? suffix.length() : 0)
+            + 128; // generous estimate for dynamic parts
+    StringBuilder sb = new StringBuilder(capacity);
+
+    // Append prefix: ddps, dddbs, ddh, dddb (preserves original field order)
+    if (prefix != null) {
+      sb.append(prefix);
+    }
+
+    // Append dynamic: ddprs
+    appendEncoded(sb, DD_PEER_SERVICE, peerService);
+
+    // Append cached static suffix: dde, ddpv
+    if (suffix != null) {
+      if (sb.length() > 0) {
+        sb.append(COMMA);
+      }
+      sb.append(suffix);
+    }
+
+    // Append dynamic: traceparent
+    appendEncoded(sb, TRACEPARENT, traceParent);
+
+    // Append conditional: ddsh
+    if (injectBaseHash) {
+      appendEncoded(sb, DD_SERVICE_HASH, baseHash);
     }
 
     return sb.length() > 0 ? sb.toString() : null;
   }
 
+  /**
+   * Initializes the cached static values (service name, env, version) from Config. These never
+   * change for the agent's lifetime. Identity-checks the Config instance to handle test scenarios
+   * where Config is rebuilt.
+   */
+  private static void ensureStaticValuesInitialized(Config config) {
+    if (cachedConfigInstance == config) {
+      return;
+    }
+    // Config instance changed (or first call) -- recompute all cached values
+    // URL-encode the service name
+    String serviceName = config.getServiceName();
+    cachedEncodedServiceName = encodeValue(serviceName);
+
+    // Build the static suffix: dde='...', ddpv='...'
+    StringBuilder sb = new StringBuilder(48);
+    appendEncoded(sb, DD_ENV, config.getEnv());
+    appendEncoded(sb, DD_VERSION, config.getVersion());
+    cachedStaticSuffix = sb.length() > 0 ? sb.toString() : null;
+
+    // Clear connection prefix cache since it includes the service name
+    connectionPrefixCache.clear();
+
+    // Publish the config instance last so other threads see all updates
+    cachedConfigInstance = config;
+  }
+
+  /**
+   * Returns a cached prefix fragment combining ddps (static service name) with dddbs, ddh, and dddb
+   * (per-connection values). This preserves the original field ordering:
+   * ddps='...',dddbs='...',ddh='...',dddb='...'
+   */
+  private static String getConnectionPrefix(String dbService, String hostname, String dbName) {
+    ConnectionKey key = new ConnectionKey(dbService, hostname, dbName);
+    String fragment = connectionPrefixCache.get(key);
+    if (fragment != null) {
+      return fragment;
+    }
+    // Build the prefix fragment preserving original order
+    StringBuilder sb = new StringBuilder(96);
+    appendPreEncoded(sb, PARENT_SERVICE, cachedEncodedServiceName);
+    appendEncoded(sb, DATABASE_SERVICE, dbService);
+    appendEncoded(sb, DD_HOSTNAME, hostname);
+    appendEncoded(sb, DD_DB_NAME, dbName);
+    fragment = sb.length() > 0 ? sb.toString() : null;
+    if (fragment != null) {
+      // Evict all entries if cache grows too large to bound memory
+      if (connectionPrefixCache.size() >= MAX_CONNECTION_CACHE_SIZE) {
+        connectionPrefixCache.clear();
+      }
+      connectionPrefixCache.put(key, fragment);
+    }
+    return fragment;
+  }
+
   private static String getPeerService() {
     AgentSpan span = activeSpan();
     Object peerService = null;
@@ -89,7 +198,36 @@ private static String encode(String val) {
     return val;
   }
 
-  private static void append(StringBuilder sb, String key, String value, int initSize) {
+  /** URL-encodes a value, returning null if the input is null or empty. */
+  private static String encodeValue(String value) {
+    if (value == null || value.isEmpty()) {
+      return null;
+    }
+    try {
+      return URLEncoder.encode(value, UTF8);
+    } catch (UnsupportedEncodingException e) {
+      return value;
+    }
+  }
+
+  /**
+   * Appends a key='already-encoded-value' pair to the StringBuilder. Used for values that have
+   * already been URL-encoded and cached.
+   */
+  private static void appendPreEncoded(StringBuilder sb, String key, String encodedValue) {
+    if (null == encodedValue || encodedValue.isEmpty()) {
+      return;
+    }
+    if (sb.length() > 0) {
+      sb.append(COMMA);
+    }
+    sb.append(key).append(EQUALS).append(QUOTE).append(encodedValue).append(QUOTE);
+  }
+
+  /**
+   * Appends an encoded key='value' pair to the StringBuilder if value is non-null and non-empty.
+   */
+  private static void appendEncoded(StringBuilder sb, String key, String value) {
     if (null == value || value.isEmpty()) {
       return;
     }
@@ -99,9 +237,59 @@ private static void append(StringBuilder sb, String key, String value, int initS
     } catch (UnsupportedEncodingException e) {
       encodedValue = value;
     }
-    if (sb.length() > initSize) {
+    if (sb.length() > 0) {
       sb.append(COMMA);
     }
     sb.append(key).append(EQUALS).append(QUOTE).append(encodedValue).append(QUOTE);
   }
+
+  /** Resets cached state. Visible for testing. */
+  static void resetCache() {
+    cachedConfigInstance = null;
+    cachedStaticSuffix = null;
+    cachedEncodedServiceName = null;
+    connectionPrefixCache.clear();
+  }
+
+  /**
+   * Composite key for per-connection prefix cache. Holds the raw (unencoded) dbService, hostname,
+   * and dbName values.
+   */
+  private static final class ConnectionKey {
+    private final String dbService;
+    private final String hostname;
+    private final String dbName;
+    private final int hashCode;
+
+    ConnectionKey(String dbService, String hostname, String dbName) {
+      this.dbService = dbService;
+      this.hostname = hostname;
+      this.dbName = dbName;
+      // Pre-compute hash code since this is an immutable key
+      int h = 17;
+      h = 31 * h + (dbService != null ? dbService.hashCode() : 0);
+      h = 31 * h + (hostname != null ? hostname.hashCode() : 0);
+      h = 31 * h + (dbName != null ? dbName.hashCode() : 0);
+      this.hashCode = h;
+    }
+
+    @Override
+    public boolean equals(Object o) {
+      if (this == o) return true;
+      if (!(o instanceof ConnectionKey)) return false;
+      ConnectionKey that = (ConnectionKey) o;
+      return equals(dbService, that.dbService)
+          && equals(hostname, that.hostname)
+          && equals(dbName, that.dbName);
+    }
+
+    private static boolean equals(String a, String b) {
+      return a == null ? b == null : a.equals(b);
+    }
+
+    @Override
+    public int hashCode() {
+      return hashCode;
+    }
+  }
 }