diff --git a/src/bitcoin-cli.cpp b/src/bitcoin-cli.cpp
index 1214b548c..8fc708be6 100644
--- a/src/bitcoin-cli.cpp
+++ b/src/bitcoin-cli.cpp
@@ -35,7 +35,7 @@ std::string HelpMessageCli()
     std::string strUsage;
     strUsage += HelpMessageGroup(_("Options:"));
     strUsage += HelpMessageOpt("-?", _("This help message"));
-    strUsage += HelpMessageOpt("-conf=<file>", strprintf(_("Specify configuration file (default: %s)"), BITCOIN_CONF_FILENAME));
+    strUsage += HelpMessageOpt("-conf=<file>", strprintf(_("Specify configuration file. Relative paths will be prefixed by datadir location. (default: %s)"), BITCOIN_CONF_FILENAME));
     strUsage += HelpMessageOpt("-datadir=<dir>", _("Specify data directory"));
     strUsage += HelpMessageOpt("-getinfo", _("Get general information from the remote server. Note that unlike server-side RPC calls, the results of -getinfo is the result of multiple non-atomic requests. Some entries in the result may represent results from different states (e.g. wallet balance may be as of a different block from the chain state reported)"));
     AppendParamsHelpMessages(strUsage);
diff --git a/src/init.cpp b/src/init.cpp
index 5e81e05f4..50643ff96 100644
--- a/src/init.cpp
+++ b/src/init.cpp
@@ -336,7 +336,7 @@ std::string HelpMessage(HelpMessageMode mode)
     strUsage += HelpMessageOpt("-blockreconstructionextratxn=<n>", strprintf(_("Extra transactions to keep in memory for compact block reconstructions (default: %u)"), DEFAULT_BLOCK_RECONSTRUCTION_EXTRA_TXN));
     if (showDebug)
         strUsage += HelpMessageOpt("-blocksonly", strprintf(_("Whether to operate in a blocks only mode (default: %u)"), DEFAULT_BLOCKSONLY));
-    strUsage += HelpMessageOpt("-conf=<file>", strprintf(_("Specify configuration file (default: %s)"), BITCOIN_CONF_FILENAME));
+    strUsage += HelpMessageOpt("-conf=<file>", strprintf(_("Specify configuration file. Relative paths will be prefixed by datadir location. (default: %s)"), BITCOIN_CONF_FILENAME));
     if (mode == HMM_BITCOIND)
     {
 #if HAVE_DECL_DAEMON
@@ -348,7 +348,7 @@ std::string HelpMessage(HelpMessageMode mode)
         strUsage += HelpMessageOpt("-dbbatchsize", strprintf("Maximum database write batch size in bytes (default: %u)", nDefaultDbBatchSize));
     }
     strUsage += HelpMessageOpt("-dbcache=<n>", strprintf(_("Set database cache size in megabytes (%d to %d, default: %d)"), nMinDbCache, nMaxDbCache, nDefaultDbCache));
-    strUsage += HelpMessageOpt("-debuglogfile=<file>", strprintf(_("Specify location of debug log file: this can be an absolute path or a path relative to the data directory (default: %s)"), DEFAULT_DEBUGLOGFILE));
+    strUsage += HelpMessageOpt("-debuglogfile=<file>", strprintf(_("Specify location of debug log file. Relative paths will be prefixed by a net-specific datadir location. (default: %s)"), DEFAULT_DEBUGLOGFILE));
     if (showDebug)
         strUsage += HelpMessageOpt("-feefilter", strprintf("Tell other nodes to filter invs to us by our mempool min fee (default: %u)", DEFAULT_FEEFILTER));
     strUsage += HelpMessageOpt("-loadblock=<file>", _("Imports blocks from external blk000??.dat file on startup"));
@@ -362,7 +362,7 @@ std::string HelpMessage(HelpMessageMode mode)
         -GetNumCores(), MAX_SCRIPTCHECK_THREADS, DEFAULT_SCRIPTCHECK_THREADS));
     strUsage += HelpMessageOpt("-persistmempool", strprintf(_("Whether to save the mempool on shutdown and load on restart (default: %u)"), DEFAULT_PERSIST_MEMPOOL));
 #ifndef WIN32
-    strUsage += HelpMessageOpt("-pid=<file>", strprintf(_("Specify pid file (default: %s)"), BITCOIN_PID_FILENAME));
+    strUsage += HelpMessageOpt("-pid=<file>", strprintf(_("Specify pid file. Relative paths will be prefixed by a net-specific datadir location. (default: %s)"), BITCOIN_PID_FILENAME));
 #endif
     strUsage += HelpMessageOpt("-prune=<n>", strprintf(_("Reduce storage requirements by enabling pruning (deleting) of old blocks. This allows the pruneblockchain RPC to be called to delete specific blocks, and enables automatic pruning of old blocks if a target size in MiB is provided. This mode is incompatible with -txindex and -rescan. "
             "Warning: Reverting this setting requires re-downloading the entire blockchain. "
@@ -500,7 +500,7 @@ std::string HelpMessage(HelpMessageMode mode)
     strUsage += HelpMessageOpt("-rpcallowip=<ip>", _("Allow JSON-RPC connections from specified source. Valid for <ip> are a single IP (e.g. 1.2.3.4), a network/netmask (e.g. 1.2.3.4/255.255.255.0) or a network/CIDR (e.g. 1.2.3.4/24). This option can be specified multiple times"));
     strUsage += HelpMessageOpt("-rpcauth=<userpw>", _("Username and hashed password for JSON-RPC connections. The field <userpw> comes in the format: <USERNAME>:<SALT>$<HASH>. A canonical python script is included in share/rpcuser. The client then connects normally using the rpcuser=<USERNAME>/rpcpassword=<PASSWORD> pair of arguments. This option can be specified multiple times"));
     strUsage += HelpMessageOpt("-rpcbind=<addr>[:port]", _("Bind to given address to listen for JSON-RPC connections. This option is ignored unless -rpcallowip is also passed. Port is optional and overrides -rpcport. Use [host]:port notation for IPv6. This option can be specified multiple times (default: 127.0.0.1 and ::1 i.e., localhost, or if -rpcallowip has been specified, 0.0.0.0 and :: i.e., all addresses)"));
-    strUsage += HelpMessageOpt("-rpccookiefile=<loc>", _("Location of the auth cookie (default: data dir)"));
+    strUsage += HelpMessageOpt("-rpccookiefile=<loc>", _("Location of the auth cookie. Relative paths will be prefixed by a net-specific datadir location. (default: data dir)"));
     strUsage += HelpMessageOpt("-rpcpassword=<pw>", _("Password for JSON-RPC connections"));
     strUsage += HelpMessageOpt("-rpcport=<port>", strprintf(_("Listen for JSON-RPC connections on <port> (default: %u or testnet: %u)"), defaultBaseParams->RPCPort(), testnetBaseParams->RPCPort()));
     strUsage += HelpMessageOpt("-rpcserialversion", strprintf(_("Sets the serialization of raw transaction or block hex returned in non-verbose mode, non-segwit(0) or segwit(1) (default: %d)"), DEFAULT_RPC_SERIALIZE_VERSION));