diff --git a/plugins/in_tail/tail_file.c b/plugins/in_tail/tail_file.c
index 25244c1df04..38b82c08d88 100644
--- a/plugins/in_tail/tail_file.c
+++ b/plugins/in_tail/tail_file.c
@@ -1267,7 +1267,17 @@ int flb_tail_file_append(char *path, struct stat *st, int mode,
                          ssize_t offset,
                          struct flb_tail_config *ctx)
 {
-    int fd;
+    /*
+     * Cleanup uses staged-goto labels in reverse acquisition order;
+     * jumping to err_X cleans up everything acquired up to and including X
+     * and falls through to subsequent labels. Each label undoes exactly one
+     * acquisition step. Construction-failure paths must NOT route through
+     * flb_tail_file_remove() because that helper increments the
+     * cmt_files_closed counter unconditionally and would unbalance the
+     * cmt_files_opened/closed pair (the matching opened increment lives at
+     * the very end of this function, immediately before return 0).
+     */
+    int fd = -1;
     int ret;
     uint64_t stream_id;
     uint64_t ts;
@@ -1305,12 +1315,14 @@ int flb_tail_file_append(char *path, struct stat *st, int mode,
     file = flb_calloc(1, sizeof(struct flb_tail_file));
     if (!file) {
         flb_errno();
-        goto error;
+        goto err_close_fd;
     }
 
     /* Initialize */
-    file->watch_fd  = -1;
+    file->config    = ctx;
     file->fd        = fd;
+    file->watch_fd  = -1;
+    file->tail_mode = mode;
 
     /* On non-windows environments check if the original path is a link */
     ret = lstat(path, &lst);
@@ -1325,7 +1337,7 @@ int flb_tail_file_append(char *path, struct stat *st, int mode,
     ret = stat_to_hash_bits(ctx, st, &hash_bits);
     if (ret != 0) {
         flb_plg_error(ctx->ins, "error procesisng hash bits for file %s", path);
-        goto error;
+        goto err_free_file;
     }
     file->hash_bits = hash_bits;
 
@@ -1333,7 +1345,7 @@ int flb_tail_file_append(char *path, struct stat *st, int mode,
     ret = stat_to_hash_key(ctx, st, &hash_key);
     if (ret != 0) {
         flb_plg_error(ctx->ins, "error procesisng hash key for file %s", path);
-        goto error;
+        goto err_free_file;
     }
     file->hash_key = hash_key;
 
@@ -1342,8 +1354,6 @@ int flb_tail_file_append(char *path, struct stat *st, int mode,
     file->size      = st->st_size;
     file->buf_len   = 0;
     file->parsed    = 0;
-    file->config    = ctx;
-    file->tail_mode = mode;
     file->tag_len   = 0;
     file->tag_buf   = NULL;
     file->rotated   = 0;
@@ -1365,7 +1375,7 @@ int flb_tail_file_append(char *path, struct stat *st, int mode,
                                              ctx->buf_max_size);
 
         if (file->decompression_context == NULL) {
-            goto error;
+            goto err_free_hash_key;
         }
     }
 
@@ -1383,7 +1393,7 @@ int flb_tail_file_append(char *path, struct stat *st, int mode,
     ret = flb_tail_file_name_dup(path, file);
     if (!file->name) {
         flb_errno();
-        goto error;
+        goto err_free_decomp;
     }
 
     /* We keep a copy of the initial filename in orig_name. This is required
@@ -1391,9 +1401,7 @@ int flb_tail_file_append(char *path, struct stat *st, int mode,
     file->orig_name = flb_strdup(file->name);
     if (!file->orig_name) {
         flb_errno();
-        flb_free(file->name);
-        file->name = NULL;
-        goto error;
+        goto err_free_name;
     }
     file->orig_name_len = file->name_len;
 
@@ -1407,7 +1415,15 @@ int flb_tail_file_append(char *path, struct stat *st, int mode,
     file->dmode_flush_timeout = 0;
     file->dmode_complete = true;
     file->dmode_buf = flb_sds_create_size(ctx->docker_mode == FLB_TRUE ? 65536 : 0);
+    if (!file->dmode_buf) {
+        flb_errno();
+        goto err_destroy_sbuf;
+    }
     file->dmode_lastline = flb_sds_create_size(ctx->docker_mode == FLB_TRUE ? 20000 : 0);
+    if (!file->dmode_lastline) {
+        flb_errno();
+        goto err_free_dmode_buf;
+    }
     file->dmode_firstline = false;
 #ifdef FLB_HAVE_SQLDB
     file->db_id     = 0;
@@ -1440,7 +1456,7 @@ int flb_tail_file_append(char *path, struct stat *st, int mode,
                           "could not create multiline stream for file: %s",
                           inode_str);
             flb_sds_destroy(inode_str);
-            goto error;
+            goto err_free_dmode_lastline;
         }
         file->ml_stream_id = stream_id;
         flb_sds_destroy(inode_str);
@@ -1461,7 +1477,7 @@ int flb_tail_file_append(char *path, struct stat *st, int mode,
     file->buf_data = flb_malloc(file->buf_size);
     if (!file->buf_data) {
         flb_errno();
-        goto error;
+        goto err_destroy_ml_stream;
     }
 
     /* Initialize (optional) dynamic tag */
@@ -1471,7 +1487,7 @@ int flb_tail_file_append(char *path, struct stat *st, int mode,
         if (!tag) {
             flb_errno();
             flb_plg_error(ctx->ins, "failed to allocate tag buffer");
-            goto error;
+            goto err_free_buf_data;
         }
 #ifdef FLB_HAVE_REGEX
         ret = tag_compose(ctx->ins->tag, ctx->tag_regex, path, tag, &tag_len, ctx);
@@ -1485,7 +1501,7 @@ int flb_tail_file_append(char *path, struct stat *st, int mode,
         flb_free(tag);
         if (ret != 0) {
             flb_plg_error(ctx->ins, "failed to compose tag for file: %s", path);
-            goto error;
+            goto err_free_buf_data;
         }
     }
     else {
@@ -1495,83 +1511,138 @@ int flb_tail_file_append(char *path, struct stat *st, int mode,
     if (!file->tag_buf) {
         flb_plg_error(ctx->ins, "failed to set tag for file: %s", path);
         flb_errno();
-        goto error;
+        goto err_free_buf_data;
     }
 
     if (mode == FLB_TAIL_STATIC) {
         mk_list_add(&file->_head, &ctx->files_static);
         ctx->files_static_count++;
-        flb_hash_table_add(ctx->static_hash, file->hash_key, flb_sds_len(file->hash_key),
-                           file, sizeof(file));
+
+        ret = flb_hash_table_add(ctx->static_hash,
+                                 file->hash_key, flb_sds_len(file->hash_key),
+                                 file, sizeof(file));
+        if (ret < 0) {
+            flb_plg_error(ctx->ins, "could not register file in static hash");
+            goto err_unlist;
+        }
+
         tail_signal_manager(file->config);
     }
     else if (mode == FLB_TAIL_EVENT) {
         mk_list_add(&file->_head, &ctx->files_event);
-        flb_hash_table_add(ctx->event_hash, file->hash_key, flb_sds_len(file->hash_key),
-                           file, sizeof(file));
+
+        ret = flb_hash_table_add(ctx->event_hash,
+                                 file->hash_key, flb_sds_len(file->hash_key),
+                                 file, sizeof(file));
+        if (ret < 0) {
+            flb_plg_error(ctx->ins, "could not register file in event hash");
+            goto err_unlist;
+        }
 
         /* Register this file into the fs_event monitoring */
         ret = flb_tail_fs_add(ctx, file);
         if (ret == -1) {
             flb_plg_error(ctx->ins, "could not register file into fs_events");
-            goto error;
+            goto err_unlist;
         }
     }
 
     /* Set the file position (database offset, head or tail) */
     ret = set_file_position(ctx, file);
     if (ret == -1) {
-        flb_tail_file_remove(file);
-        goto error;
+        goto err_fs_remove;
     }
 
     /* Remaining bytes to read */
     file->pending_bytes = file->size - file->offset;
 
-#ifdef FLB_HAVE_METRICS
-    name = (char *) flb_input_name(ctx->ins);
-    ts = cfl_time_now();
-    cmt_counter_inc(ctx->cmt_files_opened, ts, 1, (char *[]) {name});
-
-    /* Old api */
-    flb_metrics_sum(FLB_TAIL_METRIC_F_OPENED, 1, ctx->ins->metrics);
-#endif
-
     file->sl_log_event_encoder = flb_log_event_encoder_create(
                                     FLB_LOG_EVENT_FORMAT_DEFAULT);
 
     if (file->sl_log_event_encoder == NULL) {
-        flb_tail_file_remove(file);
-
-        goto error;
+        goto err_set_pos;
     }
 
     file->ml_log_event_encoder = flb_log_event_encoder_create(
                                     FLB_LOG_EVENT_FORMAT_DEFAULT);
 
     if (file->ml_log_event_encoder == NULL) {
-        flb_tail_file_remove(file);
-
-        goto error;
+        goto err_destroy_sl;
     }
 
     flb_plg_debug(ctx->ins,
                   "inode=%"PRIu64" with offset=%"PRId64" appended as %s",
                   file->inode, file->offset, path);
+
+#ifdef FLB_HAVE_METRICS
+    name = (char *) flb_input_name(ctx->ins);
+    ts = cfl_time_now();
+    cmt_counter_inc(ctx->cmt_files_opened, ts, 1, (char *[]) {name});
+
+    /* Old api */
+    flb_metrics_sum(FLB_TAIL_METRIC_F_OPENED, 1, ctx->ins->metrics);
+#endif
+
     return 0;
 
-error:
-    if (file) {
-        if (file->buf_data) {
-            flb_free(file->buf_data);
-        }
-        if (file->name) {
-            flb_free(file->name);
+/*
+ * Cleanup ladder: each label undoes exactly one acquisition and falls
+ * through to the next. Failed-acquisition gotos jump to the label that
+ * cleans up the LAST resource that was successfully acquired, skipping
+ * the cleanup of the resource that was never created.
+ */
+err_destroy_sl:
+    flb_log_event_encoder_destroy(file->sl_log_event_encoder);
+err_set_pos:
+    /* set_file_position has no resource of its own; fall through */
+err_fs_remove:
+    if (mode == FLB_TAIL_EVENT) {
+        flb_tail_fs_remove(ctx, file);
+    }
+err_unlist:
+    if (mode == FLB_TAIL_STATIC) {
+        mk_list_del(&file->_head);
+        if (ctx->files_static_count > 0) {
+            ctx->files_static_count--;
         }
-        flb_free(file);
+        flb_hash_table_del(ctx->static_hash, file->hash_key);
     }
+    else if (mode == FLB_TAIL_EVENT) {
+        mk_list_del(&file->_head);
+        flb_hash_table_del(ctx->event_hash, file->hash_key);
+    }
+    flb_free(file->tag_buf);
+err_free_buf_data:
+    flb_free(file->buf_data);
+err_destroy_ml_stream:
+    if (ctx->ml_ctx && file->ml_stream_id > 0) {
+        flb_ml_stream_id_destroy_all(ctx->ml_ctx, file->ml_stream_id);
+    }
+err_free_dmode_lastline:
+    flb_sds_destroy(file->dmode_lastline);
+err_free_dmode_buf:
+    flb_sds_destroy(file->dmode_buf);
+err_destroy_sbuf:
+    msgpack_sbuffer_destroy(&file->mult_sbuf);
+    /* orig_name was acquired immediately after name with no fallible step
+     * between, so its cleanup is folded into err_destroy_sbuf rather than
+     * carrying a label that no goto can reach */
+    flb_free(file->orig_name);
+err_free_name:
+    flb_free(file->name);
+    if (file->real_name) {
+        flb_free(file->real_name);
+    }
+err_free_decomp:
+    if (file->decompression_context) {
+        flb_decompression_context_destroy(file->decompression_context);
+    }
+err_free_hash_key:
+    flb_sds_destroy(file->hash_key);
+err_free_file:
+    flb_free(file);
+err_close_fd:
     close(fd);
-
     return -1;
 }
 
@@ -1620,6 +1691,11 @@ void flb_tail_file_remove(struct flb_tail_file *file)
 
     flb_sds_destroy(file->dmode_buf);
     flb_sds_destroy(file->dmode_lastline);
+
+    if (file->tail_mode == FLB_TAIL_STATIC && ctx->files_static_count > 0) {
+        ctx->files_static_count--;
+    }
+
     mk_list_del(&file->_head);
     flb_tail_fs_remove(ctx, file);
 
@@ -2094,14 +2170,21 @@ int flb_tail_file_to_event(struct flb_tail_file *file)
         return -1;
     }
 
+    ret = flb_hash_table_add(ctx->event_hash,
+                             file->hash_key, flb_sds_len(file->hash_key),
+                             file, sizeof(file));
+    if (ret < 0) {
+        flb_plg_error(ctx->ins, "could not register file in event hash");
+        flb_tail_fs_remove(ctx, file);
+        return -1;
+    }
+
     /* List swap: change from 'static' to 'event' list */
     mk_list_del(&file->_head);
     ctx->files_static_count--;
     flb_hash_table_del(ctx->static_hash, file->hash_key);
 
     mk_list_add(&file->_head, &file->config->files_event);
-    flb_hash_table_add(ctx->event_hash, file->hash_key, flb_sds_len(file->hash_key),
-                       file, sizeof(file));
 
     file->tail_mode = FLB_TAIL_EVENT;
 
diff --git a/plugins/in_tail/tail_fs_stat.c b/plugins/in_tail/tail_fs_stat.c
index 74b6b95dc77..18f3fb13695 100644
--- a/plugins/in_tail/tail_fs_stat.c
+++ b/plugins/in_tail/tail_fs_stat.c
@@ -246,8 +246,9 @@ int flb_tail_fs_stat_add(struct flb_tail_file *file)
 
 int flb_tail_fs_stat_remove(struct flb_tail_file *file)
 {
-    if (file->tail_mode == FLB_TAIL_EVENT) {
+    if (file->fs_backend != NULL) {
         flb_free(file->fs_backend);
+        file->fs_backend = NULL;
     }
     return 0;
 }