diff --git a/core/CoreConfig.cpp b/core/CoreConfig.cpp
index f2b32f72b9..fbdf308d21 100644
--- a/core/CoreConfig.cpp
+++ b/core/CoreConfig.cpp
@@ -318,6 +318,284 @@ inline bool IsPathSepChar(char c)
 #endif
 }
 
+void SM_ParseConfig(FILE *fp, ke::HashMap<std::string, std::string, StringPolicy> &cvars_list)
+{
+	char line[4096];
+	char cvar_name[256];
+
+	while (fgets(line, sizeof(line), fp))
+	{
+		char *ptr = line;
+
+		// Ignore whitespaces and tabs
+		while (*ptr == ' ' || *ptr == '\t')
+		{
+			ptr++;
+		}
+
+		// Ignore empty lines if found
+		if (*ptr == '\0' || *ptr == '\n' || *ptr == '\r')
+		{
+			continue;
+		}
+
+		// Ignore comments
+		if (*ptr == '/' && *(ptr + 1) == '/')
+		{
+			continue;
+		}
+
+		size_t i = 0;
+		while (*ptr != '\0' && *ptr != '\n' && *ptr != '\r' && *ptr != ' ' && *ptr != '\t' && i < (sizeof(cvar_name) - 1))
+		{
+			cvar_name[i++] = *ptr++;
+		}
+
+		cvar_name[i] = '\0';
+
+		if (!i)
+		{
+			continue;
+		}
+
+		auto p = cvars_list.findForAdd(cvar_name);
+		if (p.found())
+		{
+			continue;
+		}
+
+		// Remove spaces and tabs before the value
+		while (*ptr == ' ' || *ptr == '\t')
+		{
+        	ptr++;
+		}
+
+		char *value_start = ptr;
+		char *value_end = value_start + strlen(value_start);
+
+		while (value_end > value_start &&
+			(*(value_end - 1) == '\n' ||
+			*(value_end - 1) == '\r' ||
+			*(value_end - 1) == ' '  ||
+			*(value_end - 1) == '\t' ||
+			*(value_end - 1) == '"'))
+		{
+			value_end--;
+		}
+
+		*value_end = '\0';
+
+		if (*value_start == '"')
+		{
+			value_start++;
+		}
+
+		cvars_list.add(p, cvar_name, value_start);
+	}
+}
+
+inline bool SM_CvarExistsInConfig(ke::HashMap<std::string, std::string, StringPolicy> &cvars, const char *cvar_name)
+{
+	return cvars.find(cvar_name).found();
+}
+
+bool SM_CvarExistsInPlugin(List<const ConVar *> &convars, const char *cvar_name)
+{
+	for (List<const ConVar *>::iterator iter = convars.begin(); iter != convars.end(); iter++)
+	{
+		const ConVar *cvar = (*iter);
+#if SOURCE_ENGINE >= SE_ORANGEBOX
+		if (cvar->IsFlagSet(FCVAR_DONTRECORD))
+#else
+		if (cvar->IsBitSet(FCVAR_DONTRECORD))
+#endif
+		{
+			continue;
+		}
+
+		if (strcasecmp(cvar_name, cvar->GetName()) == 0)
+		{
+			return true;
+		}
+	}
+
+	return false;
+}
+
+bool SM_ConfigCheckRegeneration(
+	const char *file,
+	ke::HashMap<std::string, std::string, StringPolicy> &existing_cvars,
+	List<const ConVar *> &convars)
+{
+	FILE *fp = fopen(file, "rt");
+	if (!fp)
+	{
+		logger->LogError("Failed to read config for checking regeneration, make sure the directory has read permission.");
+		return true;
+	}
+
+	SM_ParseConfig(fp, existing_cvars);
+	fclose(fp);
+
+	/* #1. Check if the plugin's cvar list has a cvar that doesn't exist in the config file. */
+	for (List<const ConVar *>::iterator iter = convars.begin(); iter != convars.end(); iter++)
+	{
+		const ConVar *cvar = (*iter);
+#if SOURCE_ENGINE >= SE_ORANGEBOX
+		if (cvar->IsFlagSet(FCVAR_DONTRECORD))
+#else
+		if (cvar->IsBitSet(FCVAR_DONTRECORD))
+#endif
+		{
+			continue;
+		}
+
+		if (!SM_CvarExistsInConfig(existing_cvars, cvar->GetName()))
+		{
+			return true;
+		}
+	}
+
+	/* #2. Check if the config file has a cvar that doesn't exist in the plugin's cvar list. */
+	for (auto it = existing_cvars.iter(); !it.empty(); it.next())
+	{
+		if (!SM_CvarExistsInPlugin(convars, it->key.c_str()))
+		{
+			return true;
+		}
+	}
+
+	return false;
+}
+
+inline void SM_ExecuteConfigFile(const char *file)
+{
+	char cmd[255];
+	ke::SafeSprintf(cmd, sizeof(cmd), "exec %s\n", file);
+	engine->ServerCommand(cmd);
+}
+
+bool SM_GenerateConfigFile(
+	IPlugin *pl,
+	const char *file,
+	List<const ConVar *> &convars,
+	bool needs_regeneration = false,
+	ke::HashMap<std::string, std::string, StringPolicy> *existing_cvars = NULL)
+{
+	FILE *fp = NULL;
+	char tmp_file[PLATFORM_MAX_PATH];
+	if (!needs_regeneration)
+	{
+		fp = fopen(file, "wt");
+		if (!fp)
+		{
+			logger->LogError("Failed to auto generate config for %s, make sure the directory has write permission.", pl->GetFilename());
+			return false;
+		}
+	}
+	else
+	{
+		/* Create a .tmp file with the new contents of the new config file and then override it to the existing file */
+		ke::path::Format(tmp_file, sizeof(tmp_file), "%s.tmp", file);
+		fp = fopen(tmp_file, "wt");
+		if (!fp)
+		{
+			logger->LogError("Failed to create temp config file for %s, make sure the directory has write permission.", pl->GetFilename());
+			return false;
+		}
+	}
+
+	fprintf(fp, "// This file was auto-generated by SourceMod (v%s)\n", SOURCEMOD_VERSION);
+	fprintf(fp, "// ConVars for plugin \"%s\"\n", pl->GetFilename());
+	fprintf(fp, "\n\n");
+
+	float x;
+	for (List<const ConVar *>::iterator iter = convars.begin(); iter != convars.end(); iter++)
+	{
+		const ConVar *cvar = (*iter);
+#if SOURCE_ENGINE >= SE_ORANGEBOX
+		if (cvar->IsFlagSet(FCVAR_DONTRECORD))
+#else
+		if (cvar->IsBitSet(FCVAR_DONTRECORD))
+#endif
+		{
+			continue;
+		}
+
+		char descr[255];
+		char *dptr = descr;
+
+		/* Print comments until there is no more */
+		ke::SafeStrcpy(descr, sizeof(descr), cvar->GetHelpText());
+		while (*dptr != '\0')
+		{
+			/* Find the next line */
+			char *next_ptr = dptr;
+			while (*next_ptr != '\0')
+			{
+				if (*next_ptr == '\n')
+				{
+					*next_ptr = '\0';
+					next_ptr++;
+					break;
+				}
+				next_ptr++;
+			}
+			fprintf(fp, "// %s\n", dptr);
+			dptr = next_ptr;
+		}
+
+		fprintf(fp, "// -\n");
+		fprintf(fp, "// Default: \"%s\"\n", cvar->GetDefault());
+		if (cvar->GetMin(x))
+		{
+			fprintf(fp, "// Minimum: \"%02f\"\n", x);
+		}
+		if (cvar->GetMax(x))
+		{
+			fprintf(fp, "// Maximum: \"%02f\"\n", x);
+		}
+
+		const char *value = cvar->GetDefault();
+
+		if (needs_regeneration && existing_cvars)
+		{
+			auto p = existing_cvars->find(cvar->GetName());
+			if (p.found())
+			{
+				value = p->value.c_str();
+			}
+		}
+
+		fprintf(fp, "%s \"%s\"\n", cvar->GetName(), value);
+		fprintf(fp, "\n");
+	}
+	fprintf(fp, "\n");
+
+	fclose(fp);
+
+	if (needs_regeneration)
+	{
+#ifdef PLATFORM_WINDOWS
+		if (!MoveFileEx(tmp_file, file, MOVEFILE_REPLACE_EXISTING))
+#else
+		if (rename(tmp_file, file) != 0)
+#endif
+		{
+			/* Replacing the temp config file with the existing one failed, remove it and notify the user about it */
+			logger->LogError("Failed to replace temp config file for %s, make sure the directory has write permission.", pl->GetFilename());
+			if (remove(tmp_file) != 0)
+			{
+				logger->LogError("Failed to remove temp config file for %s.", pl->GetFilename());
+			}
+
+			return false;
+		}
+	}
+
+	return true;
+}
+
 bool SM_ExecuteConfig(IPlugin *pl, AutoConfig *cfg, bool can_create)
 {
 	bool will_create = false;
@@ -394,90 +672,62 @@ bool SM_ExecuteConfig(IPlugin *pl, AutoConfig *cfg, bool can_create)
 	g_SourceMod.BuildPath(Path_Game, file, sizeof(file), "cfg/%s", local);
 
 	bool file_exists = ke::file::IsFile(file);
-	if (!file_exists && will_create)
+
+	if (!will_create)
 	{
-		List<const ConVar *> *convars = NULL;
-		if (pl->GetProperty("ConVarList", (void **)&convars, false) && convars)
+		if (file_exists)
 		{
-			/* Attempt to create it */
-			FILE *fp = fopen(file, "wt");
-			if (fp)
-			{
-				fprintf(fp, "// This file was auto-generated by SourceMod (v%s)\n", SOURCEMOD_VERSION);
-				fprintf(fp, "// ConVars for plugin \"%s\"\n", pl->GetFilename());
-				fprintf(fp, "\n\n");
-
-				List<const ConVar *>::iterator iter;
-				float x;
-				for (iter = convars->begin(); iter != convars->end(); iter++)
-				{
-					const ConVar *cvar = (*iter);
-#if SOURCE_ENGINE >= SE_ORANGEBOX
-					if (cvar->IsFlagSet(FCVAR_DONTRECORD))
-#else
-					if (cvar->IsBitSet(FCVAR_DONTRECORD))
-#endif
-					{
-						continue;
-					}
+			SM_ExecuteConfigFile(local);
+		}
 
-					char descr[255];
-					char *dptr = descr;
+		return can_create;
+	}
 
-					/* Print comments until there is no more */
-					ke::SafeStrcpy(descr, sizeof(descr), cvar->GetHelpText());
-					while (*dptr != '\0')
-					{
-						/* Find the next line */
-						char *next_ptr = dptr;
-						while (*next_ptr != '\0')
-						{
-							if (*next_ptr == '\n')
-							{
-								*next_ptr = '\0';
-								next_ptr++;
-								break;
-							}
-							next_ptr++;
-						}
-						fprintf(fp, "// %s\n", dptr);
-						dptr = next_ptr;
-					}
+	List<const ConVar *> *convars = NULL;
+	if (!pl->GetProperty("ConVarList", (void **)&convars, false) || !convars)
+	{
+		if (file_exists)
+		{
+			SM_ExecuteConfigFile(local);
+		}
 
-					fprintf(fp, "// -\n");
-					fprintf(fp, "// Default: \"%s\"\n", cvar->GetDefault());
-					if (cvar->GetMin(x))
-					{
-						fprintf(fp, "// Minimum: \"%02f\"\n", x);
-					}
-					if (cvar->GetMax(x))
-					{
-						fprintf(fp, "// Maximum: \"%02f\"\n", x);
-					}
-					fprintf(fp, "%s \"%s\"\n", cvar->GetName(), cvar->GetDefault());
-					fprintf(fp, "\n");
-				}
-				fprintf(fp, "\n");
+		return can_create;
+	}
 
-				file_exists = true;
-				can_create = false;
-				fclose(fp);
-			}
-			else
-			{
-				logger->LogError("Failed to auto generate config for %s, make sure the directory has write permission.", pl->GetFilename());
-				return can_create;
-			}
+	if (!file_exists)
+	{
+		/* If file doesn't exist, then automatically generate the config file and execute it. */
+		/* If sourcemod somehow failed to generate the config file, then stop. */
+		if (!SM_GenerateConfigFile(pl, file, *convars))
+		{
+			return can_create;
 		}
+
+		SM_ExecuteConfigFile(local);
+		can_create = false;
+		return can_create;
 	}
 
-	if (file_exists)
+	/* Now if the file exists, read the content of it to see if we need to regenerate it or not. */
+	ke::HashMap<std::string, std::string, StringPolicy> existing_cvars;
+	existing_cvars.init();
+	if (!SM_ConfigCheckRegeneration(file, existing_cvars, *convars))
 	{
-		char cmd[255];
-		ke::SafeSprintf(cmd, sizeof(cmd), "exec %s\n", local);
-		engine->ServerCommand(cmd);
+		SM_ExecuteConfigFile(local);
+		return can_create;
+	}
+
+	/* File exists and misses cvars between the config file and the plugin's convars list
+	 * Create a temporary config file with the new contents and then override it to the existing file.
+	 * If sourcemod somehow failed to override the new contents to the existing config file, then execute the existing config file.
+	 */
+	can_create = false;
+	if (!SM_GenerateConfigFile(pl, file, *convars, true, &existing_cvars))
+	{
+		logger->LogError("An error occurred while regenerating config file for %s, executing the existing file instead.", pl->GetFilename());
 	}
 
+	SM_ExecuteConfigFile(local);
 	return can_create;
 }
 
diff --git a/core/CoreConfig.h b/core/CoreConfig.h
index f722fa4251..9a53ec66a1 100644
--- a/core/CoreConfig.h
+++ b/core/CoreConfig.h
@@ -71,6 +71,19 @@ class CoreConfig :
 	StringHashMap<std::string> m_KeyValues;
 };
 
+struct StringPolicy
+{
+	static inline uint32_t hash(const std::string &key)
+	{
+		std::string lower = ke::Lowercase(key.c_str());
+		return ke::FastHashCharSequence(lower.c_str(), lower.length());
+	}
+	static inline bool matches(const char *find, const std::string &key)
+	{
+		return strcasecmp(find, key.c_str()) == 0;
+	}
+};
+
 extern bool SM_AreConfigsExecuted();
 extern void SM_ExecuteAllConfigs();
 extern void SM_ExecuteForPlugin(IPluginContext *ctx);