diff --git a/bash_it.sh b/bash_it.sh
index ab911019..fec92c8d 100755
--- a/bash_it.sh
+++ b/bash_it.sh
@@ -1,11 +1,12 @@
 #!/usr/bin/env bash
 # Initialize Bash It
+BASH_IT_LOG_PREFIX="core: main: "
 
 # Only set $BASH_IT if it's not already set
 if [ -z "$BASH_IT" ];
 then
   # Setting $BASH to maintain backwards compatibility
-  # TODO: warn users that they should upgrade their .bash_profile
+  _log_warning "BASH_IT variable not initialized, please upgrade your bash-it version and reinstall it!"
   export BASH_IT=$BASH
   BASH="$(bash -c 'echo $BASH')"
   export BASH
@@ -14,11 +15,12 @@ fi
 # For backwards compatibility, look in old BASH_THEME location
 if [ -z "$BASH_IT_THEME" ];
 then
-  # TODO: warn users that they should upgrade their .bash_profile
+  _log_warning "BASH_IT_THEME variable not initialized, please upgrade your bash-it version and reinstall it!"
   export BASH_IT_THEME="$BASH_THEME";
   unset BASH_THEME;
 fi
 
+_log_debug "Loading composure..."
 # Load composure first, so we support function metadata
 # shellcheck source=./lib/composure.bash
 source "${BASH_IT}/lib/composure.bash"
@@ -27,11 +29,16 @@ source "${BASH_IT}/lib/composure.bash"
 cite _about _param _example _group _author _version
 
 # libraries, but skip appearance (themes) for now
+_log_debug "Loading libraries(except appearance)..."
 LIB="${BASH_IT}/lib/*.bash"
 APPEARANCE_LIB="${BASH_IT}/lib/appearance.bash"
 for _bash_it_config_file in $LIB
 do
   if [ "$_bash_it_config_file" != "$APPEARANCE_LIB" ]; then
+    filename=${_bash_it_config_file##*/}
+    filename=${filename%.bash}
+    BASH_IT_LOG_PREFIX="lib: ${filename}: "
+    _log_debug "Loading library file..."
     # shellcheck disable=SC1090
     source "$_bash_it_config_file"
   fi
@@ -51,36 +58,51 @@ done
 
 # Load theme, if a theme was set
 if [[ ! -z "${BASH_IT_THEME}" ]]; then
+  _log_debug "Loading \"${BASH_IT_THEME}\" theme..."
   # Load colors and helpers first so they can be used in base theme
+  BASH_IT_LOG_PREFIX="themes: colors: "
   # shellcheck source=./themes/colors.theme.bash
   source "${BASH_IT}/themes/colors.theme.bash"
+  BASH_IT_LOG_PREFIX="themes: githelpers: "
   # shellcheck source=./themes/githelpers.theme.bash
   source "${BASH_IT}/themes/githelpers.theme.bash"
+  BASH_IT_LOG_PREFIX="themes: p4helpers: "
   # shellcheck source=./themes/p4helpers.theme.bash
   source "${BASH_IT}/themes/p4helpers.theme.bash"
+  BASH_IT_LOG_PREFIX="themes: base: "
   # shellcheck source=./themes/base.theme.bash
   source "${BASH_IT}/themes/base.theme.bash"
 
+  BASH_IT_LOG_PREFIX="lib: appearance: "
   # appearance (themes) now, after all dependencies
   # shellcheck source=./lib/appearance.bash
   source "$APPEARANCE_LIB"
 fi
 
-# Load custom aliases, completion, plugins
+BASH_IT_LOG_PREFIX="core: main: "
+_log_debug "Loading custom aliases, completion, plugins..."
 for file_type in "aliases" "completion" "plugins"
 do
   if [ -e "${BASH_IT}/${file_type}/custom.${file_type}.bash" ]
   then
+    BASH_IT_LOG_PREFIX="${file_type}: custom: "
+    _log_debug "Loading component..."
     # shellcheck disable=SC1090
     source "${BASH_IT}/${file_type}/custom.${file_type}.bash"
   fi
 done
 
 # Custom
+BASH_IT_LOG_PREFIX="core: main: "
+_log_debug "Loading general custom files..."
 CUSTOM="${BASH_IT_CUSTOM:=${BASH_IT}/custom}/*.bash ${BASH_IT_CUSTOM:=${BASH_IT}/custom}/**/*.bash"
 for _bash_it_config_file in $CUSTOM
 do
   if [ -e "${_bash_it_config_file}" ]; then
+    filename=$(basename "${_bash_it_config_file}")
+    filename=${filename%*.bash}
+    BASH_IT_LOG_PREFIX="custom: $filename"
+    _log_debug "Loading custom file..."
     # shellcheck disable=SC1090
     source "$_bash_it_config_file"
   fi