diff --git a/cli/tests/integrations/test_ssl.py b/cli/tests/integrations/test_ssl.py
index 2696685..0319f79 100644
--- a/cli/tests/integrations/test_ssl.py
+++ b/cli/tests/integrations/test_ssl.py
@@ -52,7 +52,7 @@ def test_verify_ssl_without_cert_env_var(env):
         returncode, stdout, stderr = exec_command(
             ['dcos', 'marathon', 'app', 'list'], env)
         assert returncode == 1
-        assert "certificate verify failed" in stderr.decode('utf-8')
+        assert stderr.decode('utf-8') == _ssl_error_msg()
 
     env.pop(constants.DCOS_SSL_VERIFY_ENV)
 
@@ -62,7 +62,7 @@ def test_verify_ssl_without_cert_config(env):
         returncode, stdout, stderr = exec_command(
             ['dcos', 'marathon', 'app', 'list'], env)
         assert returncode == 1
-        assert "certificate verify failed" in stderr.decode('utf-8')
+        assert stderr.decode('utf-8') == _ssl_error_msg()
 
 
 def test_verify_ssl_with_bad_cert_env_var(env):
@@ -72,7 +72,7 @@ def test_verify_ssl_with_bad_cert_env_var(env):
         returncode, stdout, stderr = exec_command(
             ['dcos', 'marathon', 'app', 'list'], env)
         assert returncode == 1
-        assert "PEM lib" in stderr.decode('utf-8')  # wrong private key
+        assert stderr.decode('utf-8') == _ssl_error_msg()
 
     env.pop(constants.DCOS_SSL_VERIFY_ENV)
 
@@ -82,7 +82,7 @@ def test_verify_ssl_with_bad_cert_config(env):
         returncode, stdout, stderr = exec_command(
             ['dcos', 'marathon', 'app', 'list'], env)
         assert returncode == 1
-        assert "PEM lib" in stderr.decode('utf-8')  # wrong private key
+        assert stderr.decode('utf-8') == _ssl_error_msg()
 
 
 def test_verify_ssl_with_good_cert_env_var(env):
@@ -104,3 +104,10 @@ def test_verify_ssl_with_good_cert_config(env):
             ['dcos', 'marathon', 'app', 'list'], env)
         assert returncode == 0
         assert stderr == b''
+
+
+def _ssl_error_msg():
+    return (
+        "An SSL error occurred. To configure your SSL settings, please run: "
+        "`dcos config set core.ssl_verify <value>`\n"
+        "<value>: Whether to verify SSL certs for HTTPS or path to certs\n")
diff --git a/dcos/config.py b/dcos/config.py
index bb25e93..8e60fc0 100644
--- a/dcos/config.py
+++ b/dcos/config.py
@@ -213,6 +213,25 @@ def get_config_schema(command):
     return subcommand.config_schema(executable, command)
 
 
+def get_property_description(section, subkey):
+    """
+    :param section: section of config paramater
+    :type section: str
+    :param subkey: property within 'section'
+    :type subkey: str
+    :returns: description of section.subkey or None if no description
+    :rtype: str | None
+    """
+
+    schema = get_config_schema(section)
+    property_info = schema["properties"].get(subkey)
+    if property_info is not None:
+        return property_info.get("description")
+    else:
+        raise DCOSException(
+            "No schema found found for {}.{}".format(section, subkey))
+
+
 def check_config(toml_config_pre, toml_config_post):
     """
     :param toml_config_pre: dictionary for the value before change
diff --git a/dcos/data/config-schema/core.json b/dcos/data/config-schema/core.json
index 244eb47..8b19a90 100644
--- a/dcos/data/config-schema/core.json
+++ b/dcos/data/config-schema/core.json
@@ -3,13 +3,13 @@
     "additionalProperties": false,
     "properties": {
         "dcos_url": {
-            "description": "The the public master IP of your DCOS installation",
+            "description": "The public master IP of your DCOS installation",
             "format": "uri",
             "title": "DCOS URL",
             "type": "string"
         },
         "dcos_acs_token": {
-            "description": "This is the token generated by authenticating to DCOS with ACS",
+            "description": "The token generated by authenticating to DCOS with ACS",
             "title": "DCOS ACS token",
             "type": "string"
         },
diff --git a/dcos/http.py b/dcos/http.py
index 8629845..583b00c 100644
--- a/dcos/http.py
+++ b/dcos/http.py
@@ -95,6 +95,14 @@ def _request(method,
             auth=auth,
             verify=verify,
             **kwargs)
+    except requests.exceptions.SSLError as e:
+        logger.exception("HTTP SSL Error")
+        msg = ("An SSL error occurred. To configure your SSL settings, "
+               "please run: `dcos config set core.ssl_verify <value>`")
+        description = config.get_property_description("core", "ssl_verify")
+        if description is not None:
+            msg += "\n<value>: {}".format(description)
+        raise DCOSException(msg)
     except requests.exceptions.ConnectionError as e:
         logger.exception("HTTP Connection Error")
         raise DCOSException('URL [{0}] is unreachable: {1}'.format(url, e))