diff --git a/src/chat.c b/src/chat.c
index 32419d2..eee0d5f 100644
--- a/src/chat.c
+++ b/src/chat.c
@@ -1330,6 +1330,29 @@ static void chat_onDraw(ToxWindow *self, Tox *m)
     pthread_mutex_unlock(&Winthread.lock);
 }
 
+static void chat_init_log(ToxWindow *self, Tox *m, const char *self_nick)
+{
+    ChatContext *ctx = self->chatwin;
+
+    char myid[TOX_ADDRESS_SIZE];
+    tox_self_get_address(m, (uint8_t *) myid);
+
+    if (log_init(ctx->log, self_nick, myid, Friends.list[self->num].pub_key, LOG_TYPE_CHAT) != 0) {
+        line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "Failed to initialize chat log.");
+        return;
+    }
+
+    if (load_chat_history(self, ctx->log) != 0) {
+        line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "Failed to load chat history.");
+    }
+
+    if (Friends.list[self->num].logging_on) {
+        if (log_enable(ctx->log) != 0) {
+            line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "Failed to enable chat log.");
+        }
+    }
+}
+
 static void chat_onInit(ToxWindow *self, Tox *m)
 {
     curs_set(1);
@@ -1380,19 +1403,9 @@ static void chat_onInit(ToxWindow *self, Tox *m)
 
     line_info_init(ctx->hst);
 
-    char myid[TOX_ADDRESS_SIZE];
-    tox_self_get_address(m, (uint8_t *) myid);
+    chat_init_log(self, m, nick);
 
-    int log_ret = log_enable(nick, myid, Friends.list[self->num].pub_key, ctx->log, LOG_CHAT);
-    load_chat_history(self, ctx->log);
-
-    if (!Friends.list[self->num].logging_on) {
-        log_disable(ctx->log);
-    } else if (log_ret == -1) {
-        line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "Warning: Log failed to initialize.");
-    }
-
-    execute(ctx->history, self, m, "/log", GLOBAL_COMMAND_MODE);
+    execute(ctx->history, self, m, "/log", GLOBAL_COMMAND_MODE);  // Print log status to screen
 
     scrollok(ctx->history, 0);
     wmove(self->window, y2 - CURS_Y_OFFSET, 0);
diff --git a/src/conference.c b/src/conference.c
index 863b85f..2a3263c 100644
--- a/src/conference.c
+++ b/src/conference.c
@@ -114,6 +114,25 @@ static const char *conference_cmd_list[] = {
 
 static ToxWindow *new_conference_chat(uint32_t conferencenum);
 
+void conference_set_title(ToxWindow *self, uint32_t conferencesnum, const char *title, size_t length)
+{
+    ConferenceChat *chat = &conferences[conferencesnum];
+
+    if (!chat->active) {
+        return;
+    }
+
+    if (length > CONFERENCE_MAX_TITLE_LENGTH) {
+        length = CONFERENCE_MAX_TITLE_LENGTH;
+    }
+
+    memcpy(chat->title, title, length);
+    chat->title[length] = 0;
+    chat->title_length = length;
+
+    set_window_title(self, title, length);
+}
+
 static void kill_conference_window(ToxWindow *self)
 {
     ChatContext *ctx = self->chatwin;
@@ -130,8 +149,35 @@ static void kill_conference_window(ToxWindow *self)
     del_window(self);
 }
 
-int init_conference_win(Tox *m, uint32_t conferencenum, uint8_t type, const char *title,
-                        size_t title_length)
+static void init_conference_logging(ToxWindow *self, Tox *m, uint32_t conferencenum)
+{
+    ChatContext *ctx = self->chatwin;
+
+    char my_id[TOX_ADDRESS_SIZE];
+    tox_self_get_address(m, (uint8_t *) my_id);
+
+    char conference_id[TOX_CONFERENCE_ID_SIZE];
+    tox_conference_get_id(m, conferencenum, (uint8_t *) conference_id);
+
+    if (log_init(ctx->log, conferences[conferencenum].title, my_id, conference_id, LOG_TYPE_CHAT) != 0) {
+        line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "Warning: Log failed to initialize.");
+        return;
+    }
+
+    if (load_chat_history(self, ctx->log) != 0) {
+        line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "Failed to load chat history.");
+    }
+
+    if (user_settings->autolog == AUTOLOG_ON) {
+        if (log_enable(ctx->log) != 0) {
+            line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "Failed to enable chat log.");
+        }
+    }
+
+    execute(ctx->history, self, m, "/log", GLOBAL_COMMAND_MODE);  // print log state to screen
+}
+
+int init_conference_win(Tox *m, uint32_t conferencenum, uint8_t type, const char *title, size_t length)
 {
     if (conferencenum > MAX_CONFERENCE_NUM) {
         return -1;
@@ -155,7 +201,10 @@ int init_conference_win(Tox *m, uint32_t conferencenum, uint8_t type, const char
             conferences[i].last_sent_audio = 0;
 
             set_active_window_index(conferences[i].chatwin);
-            set_window_title(self, title, title_length);
+
+            conference_set_title(self, conferencenum, title, length);
+
+            init_conference_logging(self, m, conferencenum);
 
             if (i == max_conference_index) {
                 ++max_conference_index;
@@ -225,6 +274,25 @@ static void delete_conference(ToxWindow *self, Tox *m, uint32_t conferencenum)
     free_conference(self, conferencenum);
 }
 
+void conference_rename_log_path(Tox *m, uint32_t conferencenum, const char *new_title)
+{
+    ConferenceChat *chat = &conferences[conferencenum];
+
+    if (!chat->active) {
+        return;
+    }
+
+    char myid[TOX_ADDRESS_SIZE];
+    tox_self_get_address(m, (uint8_t *) myid);
+
+    char conference_id[TOX_CONFERENCE_ID_SIZE];
+    tox_conference_get_id(m, conferencenum, (uint8_t *) conference_id);
+
+    if (rename_logfile(chat->title, new_title, myid, conference_id, chat->chatwin) != 0) {
+        fprintf(stderr, "Failed to rename conference log to `%s`\n", new_title);
+    }
+}
+
 /* destroys and re-creates conference window with or without the peerlist */
 void redraw_conference_win(ToxWindow *self)
 {
@@ -319,13 +387,21 @@ static void conference_onConferenceTitleChange(ToxWindow *self, Tox *m, uint32_t
         return;
     }
 
-    set_window_title(self, title, length);
+    ConferenceChat *chat = &conferences[conferencenum];
+
+    if (!chat->active) {
+        return;
+    }
+
+    conference_rename_log_path(m, conferencenum, title);  // must be called first
+
+    conference_set_title(self, conferencenum, title, length);
 
     char timefrmt[TIME_STR_SIZE];
     get_time_str(timefrmt, sizeof(timefrmt));
 
     /* don't announce title when we join the room */
-    if (!timed_out(conferences[self->num].start_time, CONFERENCE_EVENT_WAIT)) {
+    if (!timed_out(conferences[conferencenum].start_time, CONFERENCE_EVENT_WAIT)) {
         return;
     }
 
@@ -1038,17 +1114,6 @@ static void conference_onInit(ToxWindow *self, Tox *m)
 
     line_info_init(ctx->hst);
 
-    if (user_settings->autolog == AUTOLOG_ON) {
-        char myid[TOX_ADDRESS_SIZE];
-        tox_self_get_address(m, (uint8_t *) myid);
-
-        if (log_enable(self->name, myid, NULL, ctx->log, LOG_CONFERENCE) == -1) {
-            line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "Warning: Log failed to initialize.");
-        }
-    }
-
-    execute(ctx->history, self, m, "/log", GLOBAL_COMMAND_MODE);
-
     scrollok(ctx->history, 0);
     wmove(self->window, y2 - CURS_Y_OFFSET, 0);
 }
diff --git a/src/conference.h b/src/conference.h
index 6a12684..726fb36 100644
--- a/src/conference.h
+++ b/src/conference.h
@@ -27,8 +27,9 @@
 #include "windows.h"
 
 #define SIDEBAR_WIDTH 16
-#define MAX_CONFERENCE_NUM MAX_WINDOWS_NUM - 2
+#define MAX_CONFERENCE_NUM (MAX_WINDOWS_NUM - 2)
 #define CONFERENCE_EVENT_WAIT 3
+#define CONFERENCE_MAX_TITLE_LENGTH TOX_MAX_NAME_LENGTH
 
 typedef struct ConferencePeer {
     bool       active;
@@ -64,6 +65,9 @@ typedef struct {
     int side_pos;    /* current position of the sidebar - used for scrolling up and down */
     time_t start_time;
 
+    char title[CONFERENCE_MAX_TITLE_LENGTH + 1];
+    size_t title_length;
+
     ConferencePeer *peer_list;
     uint32_t max_idx;
 
@@ -79,11 +83,15 @@ typedef struct {
 /* Frees all Toxic associated data structures for a conference (does not call tox_conference_delete() ) */
 void free_conference(ToxWindow *self, uint32_t conferencenum);
 
-int init_conference_win(Tox *m, uint32_t conferencenum, uint8_t type, const char *title, size_t title_length);
+int init_conference_win(Tox *m, uint32_t conferencenum, uint8_t type, const char *title, size_t length);
 
 /* destroys and re-creates conference window with or without the peerlist */
 void redraw_conference_win(ToxWindow *self);
 
+void conference_set_title(ToxWindow *self, uint32_t conferencesnum, const char *title, size_t length);
+void conference_rename_log_path(Tox *m, uint32_t conferencenum, const char *new_title);
+int conference_enable_logging(ToxWindow *self, Tox *m, uint32_t conferencenum, struct chatlog *log);
+
 /* Puts `(NameListEntry *)`s in `entries` for each matched peer, up to a maximum
  * of `maxpeers`.
  * Maches each peer whose name or pubkey begins with `prefix`.
diff --git a/src/conference_commands.c b/src/conference_commands.c
index 4bd9f2d..e9ad7e9 100644
--- a/src/conference_commands.c
+++ b/src/conference_commands.c
@@ -40,7 +40,7 @@ void cmd_conference_set_title(WINDOW *window, ToxWindow *self, Tox *m, int argc,
     UNUSED_VAR(window);
 
     Tox_Err_Conference_Title err;
-    char title[MAX_STR_SIZE];
+    char title[CONFERENCE_MAX_TITLE_LENGTH + 1];
 
     if (argc < 1) {
         size_t tlen = tox_conference_get_title_size(m, self->num, &err);
@@ -61,15 +61,23 @@ void cmd_conference_set_title(WINDOW *window, ToxWindow *self, Tox *m, int argc,
         return;
     }
 
+    size_t len = strlen(argv[1]);
+
+    if (len >= sizeof(title)) {
+        line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "Failed to set title: max length exceeded.");
+        return;
+    }
+
     snprintf(title, sizeof(title), "%s", argv[1]);
-    int len = strlen(title);
 
     if (!tox_conference_set_title(m, self->num, (uint8_t *) title, len, &err)) {
         line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "Failed to set title (error %d)", err);
         return;
     }
 
-    set_window_title(self, title, len);
+    conference_rename_log_path(m, self->num, title);  // must be called first
+
+    conference_set_title(self, self->num, title, len);
 
     char timefrmt[TIME_STR_SIZE];
     char selfnick[TOX_MAX_NAME_LENGTH];
diff --git a/src/friendlist.c b/src/friendlist.c
index 42a88f5..60821e5 100644
--- a/src/friendlist.c
+++ b/src/friendlist.c
@@ -453,7 +453,9 @@ static void friendlist_onNickChange(ToxWindow *self, Tox *m, uint32_t num, const
     tox_self_get_address(m, (uint8_t *) myid);
 
     if (strcmp(oldname, newnamecpy) != 0) {
-        rename_logfile(oldname, newnamecpy, myid, Friends.list[num].pub_key, Friends.list[num].chatwin);
+        if (rename_logfile(oldname, newnamecpy, myid, Friends.list[num].pub_key, Friends.list[num].chatwin) != 0) {
+            fprintf(stderr, "Failed to rename friend chat log from `%s` to `%s`\n", oldname, newnamecpy);
+        }
     }
 
     sort_friendlist_index();
diff --git a/src/global_commands.c b/src/global_commands.c
index 6918465..bc017cb 100644
--- a/src/global_commands.c
+++ b/src/global_commands.c
@@ -434,21 +434,7 @@ void cmd_log(WINDOW *window, ToxWindow *self, Tox *m, int argc, char (*argv)[MAX
     const char *swch = argv[1];
 
     if (!strcmp(swch, "1") || !strcmp(swch, "on")) {
-        char myid[TOX_ADDRESS_SIZE];
-        tox_self_get_address(m, (uint8_t *) myid);
-
-        int log_ret = -1;
-
-        if (self->type == WINDOW_TYPE_CHAT) {
-            Friends.list[self->num].logging_on = true;
-            log_ret = log_enable(self->name, myid, Friends.list[self->num].pub_key, log, LOG_CHAT);
-        } else if (self->type == WINDOW_TYPE_PROMPT) {
-            log_ret = log_enable(self->name, myid, NULL, log, LOG_PROMPT);
-        } else if (self->type == WINDOW_TYPE_CONFERENCE) {
-            log_ret = log_enable(self->name, myid, NULL, log, LOG_CONFERENCE);
-        }
-
-        msg = log_ret == 0 ? "Logging enabled." : "Warning: Log failed to initialize.";
+        msg = log_enable(log) == 0 ? "Logging enabled." : "Warning: Failed to enable log.";
         line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, msg);
         return;
     } else if (!strcmp(swch, "0") || !strcmp(swch, "off")) {
diff --git a/src/log.c b/src/log.c
index 0d0eab7..4460500 100644
--- a/src/log.c
+++ b/src/log.c
@@ -35,29 +35,33 @@
 
 extern struct user_settings *user_settings;
 
-/* There are three types of logs: chat logs, conference logs, and prompt logs (see LOG_TYPE in log.h)
-   A prompt log is in the format: LOGDIR/selfkey-home.log
-   A chat log is in the format: LOGDIR/selfkey-friendname-otherkey.log
-   A conference log is in the format: LOGDIR/selfkey-conferencename-date[time].log
-
-   Only the first (KEY_IDENT_DIGITS * 2) numbers of the key are used.
-
-   Returns 0 on success, -1 if the path is too long */
-static int get_log_path(char *dest, int destsize, char *name, const char *selfkey, const char *otherkey, int logtype)
+/* Creates a log path and puts it in `dest.
+ *
+ * There are two types of logs: chat logs and prompt logs (see LOG_TYPE in log.h)
+ * A prompt log is in the format: LOGDIR/selfkey-home.log
+ * A chat log is in the format: LOGDIR/selfkey-name-otherkey.log
+ *
+ * For friend chats `otherkey` is the first 6 bytes of the friend's Tox ID.
+ * For Conferences/groups `otherkey` is the first 6 bytes of the group's unique ID.
+ *
+ * Return path length on success.
+ * Return -1 if the path is too long.
+ */
+static int get_log_path(char *dest, int destsize, const char *name, const char *selfkey, const char *otherkey)
 {
     if (!valid_nick(name)) {
         name = UNKNOWN_NAME;
     }
 
-    const char *namedash = logtype == LOG_PROMPT ? "" : "-";
+    const char *namedash = otherkey ? "-" : "";
     const char *set_path = user_settings->chatlogs_path;
 
     char *user_config_dir = get_user_config_dir();
     int path_len = strlen(name) + strlen(".log") + strlen("-") + strlen(namedash);
     path_len += strlen(set_path) ? *set_path : strlen(user_config_dir) + strlen(LOGDIR);
 
-    /* first 6 digits of selfkey */
-    char self_id[32];
+    /* first 6 bytes of selfkey */
+    char self_id[32] = {0};
     path_len += KEY_IDENT_DIGITS * 2;
     sprintf(&self_id[0], "%02X", selfkey[0] & 0xff);
     sprintf(&self_id[2], "%02X", selfkey[1] & 0xff);
@@ -66,19 +70,13 @@ static int get_log_path(char *dest, int destsize, char *name, const char *selfke
 
     char other_id[32] = {0};
 
-    switch (logtype) {
-        case LOG_CHAT:
-            path_len += KEY_IDENT_DIGITS * 2;
-            sprintf(&other_id[0], "%02X", otherkey[0] & 0xff);
-            sprintf(&other_id[2], "%02X", otherkey[1] & 0xff);
-            sprintf(&other_id[4], "%02X", otherkey[2] & 0xff);
-            other_id[KEY_IDENT_DIGITS * 2] = '\0';
-            break;
-
-        case LOG_CONFERENCE:
-            strftime(other_id, sizeof(other_id), "%Y-%m-%d[%H:%M:%S]", get_time());
-            path_len += strlen(other_id);
-            break;
+    if (otherkey) {
+        /* first 6 bytes of otherkey */
+        path_len += KEY_IDENT_DIGITS * 2;
+        sprintf(&other_id[0], "%02X", otherkey[0] & 0xff);
+        sprintf(&other_id[2], "%02X", otherkey[1] & 0xff);
+        sprintf(&other_id[4], "%02X", otherkey[2] & 0xff);
+        other_id[KEY_IDENT_DIGITS * 2] = '\0';
     }
 
     if (path_len >= destsize) {
@@ -94,28 +92,35 @@ static int get_log_path(char *dest, int destsize, char *name, const char *selfke
 
     free(user_config_dir);
 
-    return 0;
+    return path_len;
 }
 
-/* Opens log file or creates a new one */
-static int init_logging_session(char *name, const char *selfkey, const char *otherkey, struct chatlog *log, int logtype)
+/* Initializes log path for `log`.
+ *
+ * Return 0 on success.
+ * Return -1 on failure.
+ */
+static int init_logging_session(const char *name, const char *selfkey, const char *otherkey, struct chatlog *log,
+                                LOG_TYPE type)
 {
-    if (selfkey == NULL || (logtype == LOG_CHAT && otherkey == NULL)) {
+    if (log == NULL) {
+        return -1;
+    }
+
+    if (selfkey == NULL || (type == LOG_TYPE_CHAT && otherkey == NULL)) {
         return -1;
     }
 
     char log_path[MAX_STR_SIZE];
 
-    if (get_log_path(log_path, sizeof(log_path), name, selfkey, otherkey, logtype) == -1) {
+    int path_len = get_log_path(log_path, sizeof(log_path), name, selfkey, otherkey);
+
+    if (path_len == -1 || path_len >= sizeof(log->path)) {
         return -1;
     }
 
-    log->file = fopen(log_path, "a+");
-    snprintf(log->path, sizeof(log->path), "%s", log_path);
-
-    if (log->file == NULL) {
-        return -1;
-    }
+    memcpy(log->path, log_path, path_len);
+    log->path[path_len] = 0;
 
     return 0;
 }
@@ -124,6 +129,10 @@ static int init_logging_session(char *name, const char *selfkey, const char *oth
 
 void write_to_log(const char *msg, const char *name, struct chatlog *log, bool event)
 {
+    if (log == NULL) {
+        return;
+    }
+
     if (!log->log_on) {
         return;
     }
@@ -154,94 +163,162 @@ void write_to_log(const char *msg, const char *name, struct chatlog *log, bool e
 
 void log_disable(struct chatlog *log)
 {
-    if (log->file != NULL) {
-        fclose(log->file);
+    if (log == NULL) {
+        return;
     }
 
-    *log = (struct chatlog) {
-        0
-    };
+    if (log->file != NULL) {
+        fclose(log->file);
+        log->file = NULL;
+    }
+
+    log->lastwrite = 0;
+    log->log_on = false;
 }
 
-int log_enable(char *name, const char *selfkey, const char *otherkey, struct chatlog *log, int logtype)
+int log_enable(struct chatlog *log)
 {
-    log->log_on = true;
+    if (log == NULL) {
+        return -1;
+    }
 
-    if (log->file != NULL) {
+    if (log->log_on) {
         return 0;
     }
 
-    if (init_logging_session(name, selfkey, otherkey, log, logtype) == -1) {
-        log_disable(log);
+    if (*log->path == 0) {
         return -1;
     }
 
+    if (log->file != NULL) {
+        return -1;
+    }
+
+    log->file = fopen(log->path, "a+");
+
+    if (log->file == NULL) {
+        return -1;
+    }
+
+    log->log_on = true;
+
     return 0;
 }
 
-/* Loads previous history from chat log */
-void load_chat_history(ToxWindow *self, struct chatlog *log)
+/* Initializes a log. This function must be called before any other logging operations.
+ *
+ * Return 0 on success.
+ * Return -1 on failure.
+ */
+int log_init(struct chatlog *log, const char *name, const char *selfkey, const char *otherkey, LOG_TYPE type)
 {
-    if (log->file == NULL) {
-        return;
+    if (log == NULL) {
+        return -1;
+    }
+
+    if (log->file != NULL || log->log_on) {
+        fprintf(stderr, "Warning: Called log_init() on an already initialized log\n");
+        return -1;
+    }
+
+    if (init_logging_session(name, selfkey, otherkey, log, type) == -1) {
+        return -1;
+    }
+
+    log_disable(log);
+
+    return 0;
+}
+
+/* Loads chat log history and prints it to `self` window.
+ *
+ * Return 0 on success or if log file doesn't exist.
+ * Return -1 on failure.
+ */
+int load_chat_history(ToxWindow *self, struct chatlog *log)
+{
+    if (log == NULL) {
+        return -1;
+    }
+
+    if (*log->path == 0) {
+        return -1;
     }
 
     off_t sz = file_size(log->path);
 
     if (sz <= 0) {
-        return;
+        return 0;
     }
 
-    char *hstbuf = malloc(sz + 1);
+    FILE *fp = fopen(log->path, "r");
 
-    if (hstbuf == NULL) {
-        exit_toxic_err("failed in load_chat_history", FATALERR_MEMORY);
+    if (fp == NULL) {
+        return -1;
     }
 
-    if (fseek(log->file, 0L, SEEK_SET) == -1) {
-        free(hstbuf);
-        line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, RED, " * Failed to read log file");
-        return;
+    char *buf = malloc(sz + 1);
+
+    if (buf == NULL) {
+        fclose(fp);
+        return -1;
     }
 
-    if (fread(hstbuf, sz, 1, log->file) != 1) {
-        free(hstbuf);
-        line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, RED, " * Failed to read log file");
-        return;
+    if (fseek(fp, 0L, SEEK_SET) == -1) {
+        free(buf);
+        fclose(fp);
+        return -1;
     }
 
-    hstbuf[sz] = '\0';
+    if (fread(buf, sz, 1, fp) != 1) {
+        free(buf);
+        fclose(fp);
+        return -1;
+    }
+
+    fclose(fp);
+
+    buf[sz] = 0;
 
     /* Number of history lines to load: must not be larger than MAX_LINE_INFO_QUEUE - 2 */
     int L = MIN(MAX_LINE_INFO_QUEUE - 2, user_settings->history_size);
-    int start, count = 0;
+
+    int start = 0;
+    int count = 0;
 
     /* start at end and backtrace L lines or to the beginning of buffer */
     for (start = sz - 1; start >= 0 && count < L; --start) {
-        if (hstbuf[start] == '\n') {
+        if (buf[start] == '\n') {
             ++count;
         }
     }
 
-    const char *line = strtok(&hstbuf[start + 1], "\n");
+    char *tmp = NULL;
+    const char *line = strtok_r(&buf[start + 1], "\n", &tmp);
 
     if (line == NULL) {
-        free(hstbuf);
-        return;
+        free(buf);
+        return -1;
     }
 
     while (line != NULL && count--) {
         line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "%s", line);
-        line = strtok(NULL, "\n");
+        line = strtok_r(NULL, "\n", &tmp);
     }
 
     line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "");
-    free(hstbuf);
+
+    free(buf);
+
+    return 0;
 }
 
-/* renames chatlog file replacing src with dest.
-   Returns 0 on success or if no log exists, -1 on failure. */
-int rename_logfile(char *src, char *dest, const char *selfkey, const char *otherkey, int winnum)
+/* Renames chatlog file `src` to `dest`.
+ *
+ * Return 0 on success or if no log exists.
+ * Return -1 on failure.
+ */
+int rename_logfile(const char *src, const char *dest, const char *selfkey, const char *otherkey, int winnum)
 {
     ToxWindow *toxwin = get_window_ptr(winnum);
     struct chatlog *log = NULL;
@@ -250,6 +327,11 @@ int rename_logfile(char *src, char *dest, const char *selfkey, const char *other
     /* disable log if necessary and save its state */
     if (toxwin != NULL) {
         log = toxwin->chatwin->log;
+
+        if (log == NULL) {
+            return -1;
+        }
+
         log_on = log->log_on;
     }
 
@@ -260,24 +342,38 @@ int rename_logfile(char *src, char *dest, const char *selfkey, const char *other
     char newpath[MAX_STR_SIZE];
     char oldpath[MAX_STR_SIZE];
 
-    if (get_log_path(oldpath, sizeof(oldpath), src, selfkey, otherkey, LOG_CHAT) == -1) {
+    if (get_log_path(oldpath, sizeof(oldpath), src, selfkey, otherkey) == -1) {
         goto on_error;
     }
 
     if (!file_exists(oldpath)) {
+        init_logging_session(dest, selfkey, otherkey, log, LOG_TYPE_CHAT);  // still need to rename path
         return 0;
     }
 
-    if (get_log_path(newpath, sizeof(newpath), dest, selfkey, otherkey, LOG_CHAT) == -1) {
+    int new_path_len = get_log_path(newpath, sizeof(newpath), dest, selfkey, otherkey);
+
+    if (new_path_len == -1 || new_path_len >= MAX_STR_SIZE) {
         goto on_error;
     }
 
-    if (rename(oldpath, newpath) != 0) {
-        goto on_error;
+    if (file_exists(newpath)) {
+        if (remove(oldpath) != 0) {
+            fprintf(stderr, "Failed to remove old path `%s`\n", oldpath);
+        }
+    } else {
+        if (rename(oldpath, newpath) != 0) {
+            goto on_error;
+        }
     }
 
-    if (log_on) {
-        log_enable(dest, selfkey, otherkey, log, LOG_CHAT);
+    if (log != NULL) {
+        memcpy(log->path, newpath, new_path_len);
+        log->path[new_path_len] = 0;
+
+        if (log_on) {
+            log_enable(log);
+        }
     }
 
     return 0;
@@ -285,7 +381,7 @@ int rename_logfile(char *src, char *dest, const char *selfkey, const char *other
 on_error:
 
     if (log_on) {
-        log_enable(src, selfkey, otherkey, log, LOG_CHAT);
+        log_enable(log);
     }
 
     return -1;
diff --git a/src/log.h b/src/log.h
index 6c4c61d..eb1c965 100644
--- a/src/log.h
+++ b/src/log.h
@@ -30,30 +30,43 @@ struct chatlog {
     bool log_on;    /* specific to current chat window */
 };
 
-typedef enum {
-    LOG_CONFERENCE,
-    LOG_PROMPT,
-    LOG_CHAT,
+typedef enum LOG_TYPE {
+    LOG_TYPE_PROMPT,
+    LOG_TYPE_CHAT,
 } LOG_TYPE;
 
+/* Initializes a log. This function must be called before any other logging operations.
+ *
+ * Return 0 on success.
+ * Return -1 on failure.
+ */
+int log_init(struct chatlog *log, const char *name, const char *selfkey, const char *otherkey, LOG_TYPE type);
+
 /* formats/writes line to log file */
 void write_to_log(const char *msg, const char *name, struct chatlog *log, bool event);
 
-/* enables logging for specified log and creates/fetches file if necessary.
+/* enables logging for specified log.
  *
  * Returns 0 on success.
  * Returns -1 on failure.
  */
-int log_enable(char *name, const char *selfkey, const char *otherkey, struct chatlog *log, int logtype);
+int log_enable(struct chatlog *log);
 
 /* disables logging for specified log and closes file */
 void log_disable(struct chatlog *log);
 
-/* Loads previous history from chat log */
-void load_chat_history(ToxWindow *self, struct chatlog *log);
+/* Loads chat log history and prints it to `self` window.
+ *
+ * Return 0 on success or if log file doesn't exist.
+ * Return -1 on failure.
+ */
+int load_chat_history(ToxWindow *self, struct chatlog *log);
 
-/* renames chatlog file replacing src with dest.
-   Returns 0 on success or if no log exists, -1 on failure. */
-int rename_logfile(char *src, char *dest, const char *selfkey, const char *otherkey, int winnum);
+/* Renames chatlog file `src` to `dest`.
+ *
+ * Return 0 on success or if no log exists.
+ * Return -1 on failure.
+ */
+int rename_logfile(const char *src, const char *dest, const char *selfkey, const char *otherkey, int winnum);
 
 #endif /* LOG_H */
diff --git a/src/prompt.c b/src/prompt.c
index b5960ae..8cdedb1 100644
--- a/src/prompt.c
+++ b/src/prompt.c
@@ -554,6 +554,25 @@ static void print_welcome_msg(ToxWindow *self)
     line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "");
 }
 
+static void prompt_init_log(ToxWindow *self, Tox *m, const char *self_name)
+{
+    ChatContext *ctx = self->chatwin;
+
+    char myid[TOX_ADDRESS_SIZE];
+    tox_self_get_address(m, (uint8_t *) myid);
+
+    if (log_init(ctx->log, self->name, myid, NULL, LOG_TYPE_PROMPT) != 0) {
+        line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "Warning: Log failed to initialize.");
+        return;
+    }
+
+    if (user_settings->autolog == AUTOLOG_ON) {
+        if (log_enable(ctx->log) == -1) {
+            line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "Warning: Failed to enable log.");
+        }
+    }
+}
+
 static void prompt_onInit(ToxWindow *self, Tox *m)
 {
     curs_set(1);
@@ -577,14 +596,7 @@ static void prompt_onInit(ToxWindow *self, Tox *m)
 
     line_info_init(ctx->hst);
 
-    if (user_settings->autolog == AUTOLOG_ON) {
-        char myid[TOX_ADDRESS_SIZE];
-        tox_self_get_address(m, (uint8_t *) myid);
-
-        if (log_enable(self->name, myid, NULL, ctx->log, LOG_PROMPT) == -1) {
-            line_info_add(self, NULL, NULL, NULL, SYS_MSG, 0, 0, "Warning: Log failed to initialize.");
-        }
-    }
+    prompt_init_log(self, m, self->name);
 
     scrollok(ctx->history, 0);
     wmove(self->window, y2 - CURS_Y_OFFSET, 0);