diff --git a/README.md b/README.md
index 9a044f8e..edf5e797 100644
--- a/README.md
+++ b/README.md
@@ -249,6 +249,10 @@ and how it advertises itself to a Cryostat server instance. Properties that requ
 - [ ] `cryostat.agent.harvester.max-size-b` [`long`]: the JFR `maxsize` setting, specified in bytes, to apply to periodic uploads during the application lifecycle. Defaults to `0`, which means `unlimited`.
 - [ ] `cryostat.agent.smart-trigger.definitions` [`String[]`]: a comma-separated list of Smart Trigger definitions to load at startup. Defaults to the empty string: no Smart Triggers.
 - [ ] `cryostat.agent.smart-trigger.evaluation.period-ms` [`long`]: the length of time between Smart Trigger evaluations. Default `1000`.
+- [ ] `cryostat.agent.callback.scheme` [`String`]: An override for the scheme portion of the `cryostat.agent.callback` URL (e.g. `https`).
+- [ ] `cryostat.agent.callback.host-name` [`String[]`]: An override for the host portion of the `cryostat.agent.callback` URL. Supports multiple possible host names. The first host name to resolve when paired with `cryostat.agent.callback.domain-name` will be selected. Supports an optional CEL expression that can be used to transform a provided host name. Only the host name is subject to the provided CEL expression, the domain name is not included. Syntax: `<host name>` or `<host name>[cel-expression]`, the latter evaluates the following CEL expression and uses the result as a host name candidate: `'<host name>'.cel-expression`. Example: `host1, hostx[replace("x"\\, "2")]`, the agent will try to resolve host1, followed by host2.
+- [ ] `cryostat.agent.callback.domain-name` [`String`]: An override for the domain portion of the `cryostat.agent.callback` URL. This will be appended to a resolvable host name to form the callback URL.
+- [ ] `cryostat.agent.callback.port` [`int`]: An override for the port portion of the `cryostat.agent.callback` URL.
 - [ ] `rht.insights.java.opt-out` [`boolean`]: for the Red Hat build of Cryostat, set this to true to disable data collection for Red Hat Insights. Defaults to `false`. Red Hat Insights data collection is always disabled for community builds of Cryostat.
 - [ ] `rht.insights.java.debug` [`boolean`]: for the Red Hat build of Cryostat, set this to true to enable debug logging for the Red Hat Insights Java Agent. Defaults to `false`. Red Hat Insights data collection is always disabled for community builds of Cryostat.
 
diff --git a/src/main/java/io/cryostat/agent/ConfigModule.java b/src/main/java/io/cryostat/agent/ConfigModule.java
index e2bb4675..744ae960 100644
--- a/src/main/java/io/cryostat/agent/ConfigModule.java
+++ b/src/main/java/io/cryostat/agent/ConfigModule.java
@@ -19,6 +19,7 @@
 import java.io.IOException;
 import java.net.InetAddress;
 import java.net.URI;
+import java.net.URISyntaxException;
 import java.net.URL;
 import java.net.URLClassLoader;
 import java.net.UnknownHostException;
@@ -49,8 +50,13 @@
 
 import dagger.Module;
 import dagger.Provides;
+import org.apache.http.client.utils.URIBuilder;
 import org.eclipse.microprofile.config.Config;
 import org.eclipse.microprofile.config.ConfigProvider;
+import org.projectnessie.cel.extension.StringsLib;
+import org.projectnessie.cel.tools.Script;
+import org.projectnessie.cel.tools.ScriptException;
+import org.projectnessie.cel.tools.ScriptHost;
 import org.slf4j.Logger;
 import org.slf4j.LoggerFactory;
 
@@ -208,9 +214,20 @@ public abstract class ConfigModule {
     public static final String CRYOSTAT_AGENT_SMART_TRIGGER_EVALUATION_PERIOD_MS =
             "cryostat.agent.smart-trigger.evaluation.period-ms";
 
+    public static final String CRYOSTAT_AGENT_CALLBACK_SCHEME = "cryostat.agent.callback.scheme";
+    public static final String CRYOSTAT_AGENT_CALLBACK_HOST_NAME =
+            "cryostat.agent.callback.host-name";
+    public static final String CRYOSTAT_AGENT_CALLBACK_DOMAIN_NAME =
+            "cryostat.agent.callback.domain-name";
+    public static final String CRYOSTAT_AGENT_CALLBACK_PORT = "cryostat.agent.callback.port";
+
     public static final String CRYOSTAT_AGENT_API_WRITES_ENABLED =
             "cryostat.agent.api.writes-enabled";
 
+    private static final String HOST_SCRIPT_PATTERN_STRING =
+            "(?<host>[A-Za-z0-9-.]+)(?:\\[(?<script>.+)\\])?";
+    private static final Pattern HOST_SCRIPT_PATTERN = Pattern.compile(HOST_SCRIPT_PATTERN_STRING);
+
     @Provides
     @Singleton
     public static Config provideConfig() {
@@ -251,6 +268,10 @@ public static URI provideCryostatAgentBaseUri(Config config) {
     @Singleton
     @Named(CRYOSTAT_AGENT_CALLBACK)
     public static URI provideCryostatAgentCallback(Config config) {
+        Optional<URI> callback = buildCallbackFromComponents(config);
+        if (callback.isPresent()) {
+            return callback.get();
+        }
         return config.getValue(CRYOSTAT_AGENT_CALLBACK, URI.class);
     }
 
@@ -968,4 +989,96 @@ public void clear() {
             Arrays.fill(this.buf, (byte) 0);
         }
     }
+
+    private static Optional<URI> buildCallbackFromComponents(Config config) {
+        Optional<String> scheme =
+                config.getOptionalValue(CRYOSTAT_AGENT_CALLBACK_SCHEME, String.class);
+        Optional<String[]> hostNames =
+                config.getOptionalValue(CRYOSTAT_AGENT_CALLBACK_HOST_NAME, String[].class);
+        Optional<String> domainName =
+                config.getOptionalValue(CRYOSTAT_AGENT_CALLBACK_DOMAIN_NAME, String.class);
+        Optional<Integer> port =
+                config.getOptionalValue(CRYOSTAT_AGENT_CALLBACK_PORT, Integer.class);
+        if (scheme.isPresent()
+                && hostNames.isPresent()
+                && domainName.isPresent()
+                && port.isPresent()) {
+
+            // Try resolving the each provided host name in order as a DNS name
+            Optional<String> resolvedHost =
+                    computeHostNames(hostNames.get()).stream()
+                            .sequential()
+                            .map(name -> name + "." + domainName.get())
+                            .filter(host -> tryResolveHostname(host))
+                            .findFirst();
+
+            // If none of the above resolved, then throw an error
+            if (resolvedHost.isEmpty()) {
+                throw new RuntimeException(
+                        "Failed to resolve hostname, consider disabling hostname verification in"
+                                + " Cryostat for the agent callback");
+            }
+
+            try {
+                URI result =
+                        new URIBuilder()
+                                .setScheme(scheme.get())
+                                .setHost(resolvedHost.get())
+                                .setPort(port.get())
+                                .build();
+                log.debug("Using {} for callback URL", result.toASCIIString());
+                return Optional.of(result);
+            } catch (URISyntaxException e) {
+                throw new IllegalArgumentException(e);
+            }
+        }
+        return Optional.empty();
+    }
+
+    private static List<String> computeHostNames(String[] hostNames) {
+        ScriptHost scriptHost = ScriptHost.newBuilder().build();
+        List<String> result = new ArrayList<>(hostNames.length);
+        for (String hostName : hostNames) {
+            Matcher m = HOST_SCRIPT_PATTERN.matcher(hostName);
+            if (!m.matches()) {
+                throw new RuntimeException(
+                        "Invalid hostname argument encountered: "
+                                + hostName
+                                + ". Expected format: \"hostname\" or \"hostname[cel-script]\".");
+            }
+            if (m.group("script") == null) {
+                result.add(m.group("host"));
+            } else {
+                result.add(evaluateHostnameScript(scriptHost, m.group("script"), m.group("host")));
+            }
+        }
+
+        return result;
+    }
+
+    private static String evaluateHostnameScript(
+            ScriptHost scriptHost, String scriptText, String hostname) {
+        try {
+            Script script =
+                    scriptHost
+                            .buildScript("\"" + hostname + "\"." + scriptText)
+                            .withLibraries(new StringsLib())
+                            .build();
+            Map<String, Object> args = new HashMap<>();
+            return script.execute(String.class, args);
+        } catch (ScriptException e) {
+            throw new RuntimeException("Failed to execute provided CEL script", e);
+        }
+    }
+
+    private static boolean tryResolveHostname(String hostname) {
+        try {
+            log.debug("Attempting to resolve {}", hostname);
+            InetAddress addr = InetAddress.getByName(hostname);
+            log.debug("Resolved {} to {}", hostname, addr.getHostAddress());
+            return true;
+        } catch (UnknownHostException ignored) {
+            return false;
+        }
+    }
 }
diff --git a/src/test/java/io/cryostat/agent/ConfigModuleTest.java b/src/test/java/io/cryostat/agent/ConfigModuleTest.java
new file mode 100644
index 00000000..a2d9036d
--- /dev/null
+++ b/src/test/java/io/cryostat/agent/ConfigModuleTest.java
@@ -0,0 +1,113 @@
+/*
+ * Copyright The Cryostat 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
+ *
+ * http://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 io.cryostat.agent;
+
+import static org.junit.jupiter.api.Assertions.assertEquals;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+import static org.mockito.Mockito.when;
+
+import java.net.InetAddress;
+import java.net.URI;
+import java.net.UnknownHostException;
+import java.util.Optional;
+
+import org.eclipse.microprofile.config.Config;
+import org.junit.jupiter.api.AfterEach;
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.ExtendWith;
+import org.mockito.Mock;
+import org.mockito.MockedStatic;
+import org.mockito.Mockito;
+import org.mockito.junit.jupiter.MockitoExtension;
+
+@ExtendWith(MockitoExtension.class)
+public class ConfigModuleTest {
+
+    @Mock Config config;
+    @Mock InetAddress addr;
+    MockedStatic<InetAddress> addrMock;
+
+    @BeforeEach
+    void setupEach() throws Exception {
+        addrMock = Mockito.mockStatic(InetAddress.class);
+    }
+
+    @AfterEach
+    void teardownEach() {
+        addrMock.close();
+    }
+
+    @Test
+    void testCallback() throws Exception {
+        when(config.getValue(ConfigModule.CRYOSTAT_AGENT_CALLBACK, URI.class))
+                .thenReturn(new URI("https://callback.example.com:9977"));
+
+        URI result = ConfigModule.provideCryostatAgentCallback(config);
+        assertEquals("https://callback.example.com:9977", result.toASCIIString());
+    }
+
+    @Test
+    void testCallbackComponentsHostname() throws Exception {
+        setupCallbackComponents();
+
+        when(addr.getHostAddress()).thenReturn("10.2.3.4");
+        addrMock.when(() -> InetAddress.getByName("foo.headless.svc.example.com")).thenReturn(addr);
+
+        URI result = ConfigModule.provideCryostatAgentCallback(config);
+        assertEquals("https://foo.headless.svc.example.com:9977", result.toASCIIString());
+    }
+
+    @Test
+    void testCallbackComponentsDashedIP() throws Exception {
+        setupCallbackComponents();
+
+        when(addr.getHostAddress()).thenReturn("10.2.3.4");
+        addrMock.when(() -> InetAddress.getByName("foo.headless.svc.example.com"))
+                .thenThrow(new UnknownHostException("TEST"));
+        addrMock.when(() -> InetAddress.getByName("10-2-3-4.headless.svc.example.com"))
+                .thenReturn(addr);
+
+        URI result = ConfigModule.provideCryostatAgentCallback(config);
+        assertEquals("https://10-2-3-4.headless.svc.example.com:9977", result.toASCIIString());
+    }
+
+    @Test
+    void testCallbackComponentsNoMatch() throws Exception {
+        setupCallbackComponents();
+
+        addrMock.when(() -> InetAddress.getByName("foo.headless.svc.example.com"))
+                .thenThrow(new UnknownHostException("TEST"));
+        addrMock.when(() -> InetAddress.getByName("10-2-3-4.headless.svc.example.com"))
+                .thenThrow(new UnknownHostException("TEST"));
+
+        assertThrows(
+                RuntimeException.class, () -> ConfigModule.provideCryostatAgentCallback(config));
+    }
+
+    private void setupCallbackComponents() {
+        when(config.getOptionalValue(
+                        ConfigModule.CRYOSTAT_AGENT_CALLBACK_DOMAIN_NAME, String.class))
+                .thenReturn(Optional.of("headless.svc.example.com"));
+        when(config.getOptionalValue(
+                        ConfigModule.CRYOSTAT_AGENT_CALLBACK_HOST_NAME, String[].class))
+                .thenReturn(Optional.of(new String[] {"foo", "10.2.3.4[replace(\".\", \"-\")]"}));
+        when(config.getOptionalValue(ConfigModule.CRYOSTAT_AGENT_CALLBACK_PORT, Integer.class))
+                .thenReturn(Optional.of(9977));
+        when(config.getOptionalValue(ConfigModule.CRYOSTAT_AGENT_CALLBACK_SCHEME, String.class))
+                .thenReturn(Optional.of("https"));
+    }
+}