diff --git a/src/main/java/com/googlesource/gerrit/plugins/its/jira/InitJira.java b/src/main/java/com/googlesource/gerrit/plugins/its/jira/InitJira.java
index 0f9e19a..77d2b1b 100644
--- a/src/main/java/com/googlesource/gerrit/plugins/its/jira/InitJira.java
+++ b/src/main/java/com/googlesource/gerrit/plugins/its/jira/InitJira.java
@@ -25,6 +25,8 @@
 import com.googlesource.gerrit.plugins.its.base.its.InitIts;
 import com.googlesource.gerrit.plugins.its.base.validation.ItsAssociationPolicy;
 import java.io.IOException;
+import java.net.MalformedURLException;
+import java.net.URL;
 import java.util.Arrays;
 import org.eclipse.jgit.errors.ConfigInvalidException;
 
@@ -35,7 +37,7 @@
   private final Section.Factory sections;
   private final InitFlags flags;
   private Section jira;
-  private String jiraUrl;
+  private URL jiraUrl;
   private String jiraUsername;
   private String jiraPassword;
 
@@ -89,13 +91,14 @@
     }
   }
 
-  private void init() {
+  private void init() throws MalformedURLException {
     this.jira = sections.get(pluginName, null);
     Section jiraComment = sections.get(COMMENT_LINK_SECTION, pluginName);
 
     do {
       enterJiraConnectivity();
-    } while (jiraUrl != null && (isConnectivityRequested(jiraUrl) && !isJiraConnectSuccessful()));
+    } while (jiraUrl != null
+        && (isConnectivityRequested(jiraUrl.toString()) && !isJiraConnectSuccessful()));
 
     if (jiraUrl == null) {
       return;
@@ -111,9 +114,10 @@
         "Issue-id enforced in commit message", "association", ItsAssociationPolicy.SUGGESTED);
   }
 
-  public void enterJiraConnectivity() {
-    jiraUrl = jira.string("Jira URL (empty to skip)", "url", null);
-    if (jiraUrl != null) {
+  public void enterJiraConnectivity() throws MalformedURLException {
+    String jiraUrlString = jira.string("Jira URL (empty to skip)", "url", null);
+    if (jiraUrlString != null) {
+      jiraUrl = new URL(jiraUrlString);
       jiraUsername = jira.string("Jira username", "username", "");
       jiraPassword = jira.password("username", "password");
     }
diff --git a/src/main/java/com/googlesource/gerrit/plugins/its/jira/JiraClient.java b/src/main/java/com/googlesource/gerrit/plugins/its/jira/JiraClient.java
index ae2a864..7311a9b 100644
--- a/src/main/java/com/googlesource/gerrit/plugins/its/jira/JiraClient.java
+++ b/src/main/java/com/googlesource/gerrit/plugins/its/jira/JiraClient.java
@@ -31,7 +31,7 @@
 import com.googlesource.gerrit.plugins.its.jira.restapi.JiraServerInfo;
 import com.googlesource.gerrit.plugins.its.jira.restapi.JiraTransition;
 import java.io.IOException;
-import java.net.MalformedURLException;
+import java.net.URL;
 import java.util.Arrays;
 import java.util.List;
 import org.slf4j.Logger;
@@ -44,7 +44,7 @@
   private final Gson gson;
 
   @Inject
-  public JiraClient(JiraConfig jiraConfig) throws MalformedURLException {
+  public JiraClient(JiraConfig jiraConfig) {
     this(jiraConfig.getJiraUrl(), jiraConfig.getUsername(), jiraConfig.getPassword());
   }
 
@@ -55,7 +55,7 @@
    * @param user username of the jira user
    * @param pass password of the jira user
    */
-  JiraClient(String url, String user, String pass) throws MalformedURLException {
+  JiraClient(URL url, String user, String pass) {
     this.apiBuilder = new JiraRestApiProvider(url, user, pass);
     this.gson = new Gson();
   }
diff --git a/src/main/java/com/googlesource/gerrit/plugins/its/jira/JiraConfig.java b/src/main/java/com/googlesource/gerrit/plugins/its/jira/JiraConfig.java
index b757b65..9ec5d9b 100644
--- a/src/main/java/com/googlesource/gerrit/plugins/its/jira/JiraConfig.java
+++ b/src/main/java/com/googlesource/gerrit/plugins/its/jira/JiraConfig.java
@@ -14,23 +14,26 @@
 
 package com.googlesource.gerrit.plugins.its.jira;
 
+import static com.googlesource.gerrit.plugins.its.jira.UrlHelper.*;
 import static java.lang.String.format;
 
 import com.google.gerrit.extensions.annotations.PluginName;
 import com.google.gerrit.server.config.GerritServerConfig;
 import com.google.inject.Inject;
 import com.google.inject.Singleton;
+import java.net.MalformedURLException;
+import java.net.URL;
 import org.eclipse.jgit.lib.Config;
 
 /** The JIRA plugin configuration as read from Gerrit config. */
 @Singleton
 public class JiraConfig {
-  static final String ERROR_MSG = "Unable to load plugin %s. Cause: Wrong configuration ";
+  static final String ERROR_MSG = "Unable to load plugin %s because of invalid configuration: %s";
   static final String GERRIT_CONFIG_URL = "url";
   static final String GERRIT_CONFIG_USERNAME = "username";
   static final String GERRIT_CONFIG_PASSWORD = "password";
 
-  private final String jiraUrl;
+  private final URL jiraUrl;
   private final String jiraUsername;
   private final String jiraPassword;
 
@@ -42,11 +45,16 @@
    */
   @Inject
   JiraConfig(@GerritServerConfig Config config, @PluginName String pluginName) {
-    jiraUrl = config.getString(pluginName, null, GERRIT_CONFIG_URL);
+    try {
+      jiraUrl = adjustUrlPath(new URL(config.getString(pluginName, null, GERRIT_CONFIG_URL)));
+    } catch (MalformedURLException e) {
+      throw new RuntimeException(format(ERROR_MSG, pluginName, e.getLocalizedMessage()));
+    }
+
     jiraUsername = config.getString(pluginName, null, GERRIT_CONFIG_USERNAME);
     jiraPassword = config.getString(pluginName, null, GERRIT_CONFIG_PASSWORD);
     if (jiraUrl == null || jiraUsername == null || jiraPassword == null) {
-      throw new RuntimeException(format(ERROR_MSG, pluginName));
+      throw new RuntimeException(format(ERROR_MSG, pluginName, "missing username/password"));
     }
   }
 
@@ -55,7 +63,7 @@
    *
    * @return the jira url
    */
-  public String getJiraUrl() {
+  public URL getJiraUrl() {
     return jiraUrl;
   }
 
diff --git a/src/main/java/com/googlesource/gerrit/plugins/its/jira/UrlHelper.java b/src/main/java/com/googlesource/gerrit/plugins/its/jira/UrlHelper.java
new file mode 100644
index 0000000..a6b89ef
--- /dev/null
+++ b/src/main/java/com/googlesource/gerrit/plugins/its/jira/UrlHelper.java
@@ -0,0 +1,37 @@
+
+package com.googlesource.gerrit.plugins.its.jira;
+
+import java.net.MalformedURLException;
+import java.net.URL;
+import java.util.Arrays;
+import org.slf4j.Logger;
+import org.slf4j.LoggerFactory;
+
+public class UrlHelper {
+  private static final Logger log = LoggerFactory.getLogger(UrlHelper.class);
+
+  public static URL resolveUrl(URL url, String... paths) {
+    if (url == null) {
+      return url;
+    }
+
+    String relativePath = String.join("", Arrays.asList(paths));
+    try {
+      return new URL(url, relativePath);
+    } catch (MalformedURLException e) {
+      log.error("Unexpected exception while composing URL {} with path {}", url, relativePath, e);
+      throw new IllegalArgumentException(e);
+    }
+  }
+
+  public static URL adjustUrlPath(URL url) {
+    if (url == null) {
+      return url;
+    }
+    try {
+      return url.getPath().endsWith("/") ? url : new URL(url, "/");
+    } catch (MalformedURLException e) {
+      throw new RuntimeException(e);
+    }
+  }
+}
diff --git a/src/main/java/com/googlesource/gerrit/plugins/its/jira/restapi/JiraRestApi.java b/src/main/java/com/googlesource/gerrit/plugins/its/jira/restapi/JiraRestApi.java
index aff8428..35f70ce 100644
--- a/src/main/java/com/googlesource/gerrit/plugins/its/jira/restapi/JiraRestApi.java
+++ b/src/main/java/com/googlesource/gerrit/plugins/its/jira/restapi/JiraRestApi.java
@@ -14,12 +14,13 @@
 
 package com.googlesource.gerrit.plugins.its.jira.restapi;
 
+import static com.googlesource.gerrit.plugins.its.jira.UrlHelper.*;
+
 import com.google.gson.Gson;
 import java.io.IOException;
 import java.io.InputStreamReader;
 import java.io.OutputStream;
 import java.net.HttpURLConnection;
-import java.net.MalformedURLException;
 import java.net.Proxy;
 import java.net.ProxySelector;
 import java.net.URL;
@@ -45,10 +46,9 @@
    * @param user username of the jira user
    * @param pass password of the jira user
    */
-  JiraRestApi(URL url, String user, String pass, Class<T> classOfT, String classPrefix)
-      throws MalformedURLException {
+  JiraRestApi(URL url, String user, String pass, Class<T> classOfT, String classPrefix) {
     this.auth = Base64.getEncoder().encodeToString((user + ":" + pass).getBytes());
-    this.baseUrl = new URL(url, BASE_PREFIX + classPrefix + "/");
+    this.baseUrl = resolveUrl(url, BASE_PREFIX, classPrefix, "/");
     this.gson = new Gson();
     this.classOfT = classOfT;
   }
diff --git a/src/main/java/com/googlesource/gerrit/plugins/its/jira/restapi/JiraRestApiProvider.java b/src/main/java/com/googlesource/gerrit/plugins/its/jira/restapi/JiraRestApiProvider.java
index 3277f7f..37534a5 100644
--- a/src/main/java/com/googlesource/gerrit/plugins/its/jira/restapi/JiraRestApiProvider.java
+++ b/src/main/java/com/googlesource/gerrit/plugins/its/jira/restapi/JiraRestApiProvider.java
@@ -14,7 +14,6 @@
 
 package com.googlesource.gerrit.plugins.its.jira.restapi;
 
-import java.net.MalformedURLException;
 import java.net.URL;
 
 public class JiraRestApiProvider {
@@ -22,26 +21,25 @@
   private final String user;
   private final String pass;
 
-  public JiraRestApiProvider(String url, String user, String pass) throws MalformedURLException {
-    this.url = new URL(url + (url.endsWith("/") ? "" : "/"));
+  public JiraRestApiProvider(URL url, String user, String pass) {
+    this.url = url;
     this.user = user;
     this.pass = pass;
   }
 
-  public <T> JiraRestApi<T> get(Class<T> classOfT, String classPrefix)
-      throws MalformedURLException {
+  public <T> JiraRestApi<T> get(Class<T> classOfT, String classPrefix) {
     return new JiraRestApi<>(url, user, pass, classOfT, classPrefix);
   }
 
-  public JiraRestApi<JiraIssue> getIssue() throws MalformedURLException {
+  public JiraRestApi<JiraIssue> getIssue() {
     return get(JiraIssue.class, "/issue");
   }
 
-  public JiraRestApi<JiraServerInfo> getServerInfo() throws MalformedURLException {
+  public JiraRestApi<JiraServerInfo> getServerInfo() {
     return get(JiraServerInfo.class, "/serverInfo");
   }
 
-  public JiraRestApi<JiraProject[]> getProjects() throws MalformedURLException {
+  public JiraRestApi<JiraProject[]> getProjects() {
     return get(JiraProject[].class, "/project");
   }
 }
diff --git a/src/test/java/com/googlesource/gerrit/plugins/its/jira/JiraConfigTest.java b/src/test/java/com/googlesource/gerrit/plugins/its/jira/JiraConfigTest.java
index f7f5a40..fba7db7 100644
--- a/src/test/java/com/googlesource/gerrit/plugins/its/jira/JiraConfigTest.java
+++ b/src/test/java/com/googlesource/gerrit/plugins/its/jira/JiraConfigTest.java
@@ -15,13 +15,13 @@
 package com.googlesource.gerrit.plugins.its.jira;
 
 import static com.google.common.truth.Truth.assertThat;
-import static com.googlesource.gerrit.plugins.its.jira.JiraConfig.ERROR_MSG;
 import static com.googlesource.gerrit.plugins.its.jira.JiraConfig.GERRIT_CONFIG_PASSWORD;
 import static com.googlesource.gerrit.plugins.its.jira.JiraConfig.GERRIT_CONFIG_URL;
 import static com.googlesource.gerrit.plugins.its.jira.JiraConfig.GERRIT_CONFIG_USERNAME;
-import static java.lang.String.format;
 import static org.mockito.Mockito.when;
 
+import java.net.MalformedURLException;
+import java.net.URL;
 import org.eclipse.jgit.lib.Config;
 import org.junit.Rule;
 import org.junit.Test;
@@ -34,7 +34,7 @@
 public class JiraConfigTest {
 
   private static final String PASS = "pass";
-  private static final String URL = "http://jira_example.com";
+  private static final URL TEST_URL = newUrl("http://jira_example.com/");
   private static final String USER = "user";
   private static final String PLUGIN_NAME = "its-jira";
 
@@ -45,19 +45,26 @@
 
   @Test
   public void gerritConfigContainsSaneValues() throws Exception {
-    when(cfg.getString(PLUGIN_NAME, null, GERRIT_CONFIG_URL)).thenReturn(URL);
+    when(cfg.getString(PLUGIN_NAME, null, GERRIT_CONFIG_URL)).thenReturn(TEST_URL.toString());
     when(cfg.getString(PLUGIN_NAME, null, GERRIT_CONFIG_USERNAME)).thenReturn(USER);
     when(cfg.getString(PLUGIN_NAME, null, GERRIT_CONFIG_PASSWORD)).thenReturn(PASS);
     jiraConfig = new JiraConfig(cfg, PLUGIN_NAME);
     assertThat(jiraConfig.getUsername()).isEqualTo(USER);
     assertThat(jiraConfig.getPassword()).isEqualTo(PASS);
-    assertThat(jiraConfig.getJiraUrl()).isEqualTo(URL);
+    assertThat(jiraConfig.getJiraUrl()).isEqualTo(TEST_URL);
   }
 
   @Test
   public void gerritConfigContainsNullValues() throws Exception {
     thrown.expect(RuntimeException.class);
-    thrown.expectMessage(format(ERROR_MSG, PLUGIN_NAME));
     jiraConfig = new JiraConfig(cfg, PLUGIN_NAME);
   }
+
+  private static URL newUrl(String url) {
+    try {
+      return new URL(url);
+    } catch (MalformedURLException e) {
+      throw new RuntimeException(e);
+    }
+  }
 }
diff --git a/src/test/java/com/googlesource/gerrit/plugins/its/jira/restapi/JiraRestApiTest.java b/src/test/java/com/googlesource/gerrit/plugins/its/jira/restapi/JiraRestApiTest.java
index 24512b5..b87b591 100644
--- a/src/test/java/com/googlesource/gerrit/plugins/its/jira/restapi/JiraRestApiTest.java
+++ b/src/test/java/com/googlesource/gerrit/plugins/its/jira/restapi/JiraRestApiTest.java
@@ -16,37 +16,38 @@
 
 import static com.google.common.truth.Truth.assertThat;
 
+import java.net.URL;
 import org.junit.Test;
 
 public class JiraRestApiTest {
 
   @Test
   public void testJiraServerInfoForNonRootJiraUrl() throws Exception {
-    String nonRootJiraUrl = "http://jira.mycompany.com/myroot/";
+    URL nonRootJiraUrl = new URL("http://jira.mycompany.com/myroot/");
     JiraRestApi<JiraServerInfo> serverInfo =
         new JiraRestApiProvider(nonRootJiraUrl, "", "").getServerInfo();
 
     String jiraApiUrl = serverInfo.getBaseUrl().toString();
-    assertThat(jiraApiUrl).startsWith(nonRootJiraUrl);
+    assertThat(jiraApiUrl).startsWith(nonRootJiraUrl.toString());
   }
 
   @Test
   public void testJiraServerInfoForNonRootJiraUrlNotEndingWithSlash() throws Exception {
-    String nonRootJiraUrl = "http://jira.mycompany.com/myroot";
+    URL nonRootJiraUrl = new URL("http://jira.mycompany.com/myroot/");
     JiraRestApi<JiraServerInfo> serverInfo =
         new JiraRestApiProvider(nonRootJiraUrl, "", "").getServerInfo();
 
     String jiraApiUrl = serverInfo.getBaseUrl().toString();
-    assertThat(jiraApiUrl).startsWith(nonRootJiraUrl);
+    assertThat(jiraApiUrl).startsWith(nonRootJiraUrl.toString());
   }
 
   @Test
   public void testJiraServerInfoForRootJiraUrl() throws Exception {
-    String rootJiraUrl = "http://jira.mycompany.com";
+    URL rootJiraUrl = new URL("http://jira.mycompany.com");
     JiraRestApi<JiraServerInfo> serverInfo =
         new JiraRestApiProvider(rootJiraUrl, "", "").getServerInfo();
 
     String jiraApiUrl = serverInfo.getBaseUrl().toString();
-    assertThat(jiraApiUrl).startsWith(rootJiraUrl);
+    assertThat(jiraApiUrl).startsWith(rootJiraUrl.toString());
   }
 }