diff --git a/NEWS.md b/NEWS.md
index 3abcdaed4..f5fe08f92 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -251,6 +251,8 @@
     # 3:     3    NA
     # 4:     4    NA
     ```
+    
+32. `fread()` already made a good guess as to whether column names are present by comparing the type of the fields in row 1 to the type of the fields in the sample. This guess is now improved when a column contains a string in row 1 (i.e. a potential column name) but all blank in the sample rows, [#2526](https://github.com/Rdatatable/data.table/issues/2526). Thanks @st-pasha for reporting, and @ben-schwen for the PR.
 
 ## BUG FIXES
 
diff --git a/inst/tests/tests.Rraw b/inst/tests/tests.Rraw
index 0b77d98fa..8982342bc 100644
--- a/inst/tests/tests.Rraw
+++ b/inst/tests/tests.Rraw
@@ -12498,9 +12498,12 @@ if (test_R.utils) {
 }
 
 # better colname detection by comparing potential column names to the whole sample not just the first row of the sample, #2526
-test(1870.1, fread("A,100,200\n,300,400\n,500,600"), data.table(A=NA, "100"=c(300L,500L), "200"=c(400L,600L)))
-test(1870.2, fread("A,100,\n,,\n,500,600"), data.table(A=NA, "100"=c(NA,500L), V3=c(NA,600L)))
+test(1870.1, fread("A,100,200\n,300,400\n,500,600"), data.table(V1=c("A","",""), V2=c(100L,300L,500L), V3=c(200L,400L,600L)))
+test(1870.2, fread("A,100,\n,,\n,500,600"), data.table(V1=c("A","",""), V2=c(100L,NA,500L), V3=c(NA,NA,600L)))
 test(1870.3, fread("A,B,\n,,\n,500,3.4"), data.table(A=NA, B=c(NA,500L), V3=c(NA,3.4)))
+test(1870.4, fread("A,B,200\n,300,400\n,500,600"), data.table(A=NA, B=c(300L,500L), "200"=c(400L,600L)))
+test(1870.5, fread("A,B,\n,,\n,500,600"), data.table(A=NA, B=c(NA,500L), V3=c(NA,600L)))
+test(1870.6, fread("A,,\n,300,400\n,500,600"), data.table(V1=c("A","",""), V2=c(NA,300L,500L), V3=c(NA,400L,600L)))
 
 # nrows= now ignores errors after those nrows as expected and skip= determines first row for sure, #1267
 txt = "V1, V2, V3\n2,3,4\nV4, V5, V6, V7\n4,5,6,7\n8,9,10,11\n"
diff --git a/src/fread.c b/src/fread.c
index 2aa796037..04df88d9c 100644
--- a/src/fread.c
+++ b/src/fread.c
@@ -66,8 +66,8 @@ static int8_t *type = NULL, *tmpType = NULL, *size = NULL;
 static lenOff *colNames = NULL;
 static freadMainArgs args = {0};  // global for use by DTPRINT; static implies ={0} but include the ={0} anyway just in case for valgrind #4639
 
-const char typeName[NUMTYPE][10] = {"drop", "bool8", "bool8", "bool8", "bool8", "int32", "int64", "float64", "float64", "float64", "int32", "float64", "string"};
-int8_t     typeSize[NUMTYPE]     = { 0,      1,       1,       1,       1,       4,       8,       8,         8,         8,         4,       8       ,  8      };
+const char typeName[NUMTYPE][10] = {"drop", "bool8", "bool8", "bool8", "bool8", "bool8", "int32", "int64", "float64", "float64", "float64", "int32", "float64", "string"};
+int8_t     typeSize[NUMTYPE]     = { 0,      1,       1,       1,       1,       1,       4,       8,       8,         8,         8,         4,       8       ,  8      };
 
 // In AIX, NAN and INFINITY don't qualify as constant literals. Refer: PR #3043
 // So we assign them through below init function.
@@ -1076,6 +1076,12 @@ static void parse_iso8601_timestamp(FieldParseContext *ctx)
     *target = NA_FLOAT64;
 }
 
+static void parse_empty(FieldParseContext *ctx)
+{
+  int8_t *target = (int8_t*) ctx->targets[sizeof(int8_t)];
+  *target = NA_BOOL8;
+}
+
 /* Parse numbers 0 | 1 as boolean and ,, as NA (fwrite's default) */
 static void parse_bool_numeric(FieldParseContext *ctx)
 {
@@ -1152,7 +1158,8 @@ static void parse_bool_lowercase(FieldParseContext *ctx)
  */
 typedef void (*reader_fun_t)(FieldParseContext *ctx);
 static reader_fun_t fun[NUMTYPE] = {
-  (reader_fun_t) &Field,
+  (reader_fun_t) &Field,        // CT_DROP
+  (reader_fun_t) &parse_empty,  // CT_EMPTY
   (reader_fun_t) &parse_bool_numeric,
   (reader_fun_t) &parse_bool_uppercase,
   (reader_fun_t) &parse_bool_titlecase,
@@ -1167,7 +1174,7 @@ static reader_fun_t fun[NUMTYPE] = {
   (reader_fun_t) &Field
 };
 
-static int disabled_parsers[NUMTYPE] = {0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0};
+static int disabled_parsers[NUMTYPE] = {0};
 
 static int detect_types( const char **pch, int8_t type[], int ncol, bool *bumped) {
   // used in sampling column types and whether column names are present
@@ -1883,8 +1890,7 @@ int freadMain(freadMainArgs _args) {
     bool bumped=false;
     detect_types(&ch, tmpType, ncol, &bumped);
     if (sampleLines>0) for (int j=0; j<ncol; j++) {
-      if (tmpType[j]==CT_STRING && type[j]<CT_STRING) {
-        // includes an all-blank column with a string at the top; e.g. test 1870.1 and 1870.2
+      if (tmpType[j]==CT_STRING && type[j]<CT_STRING && type[j]>CT_EMPTY) {
         args.header=true;
         if (verbose) DTPRINT(_("  'header' determined to be true due to column %d containing a string on row 1 and a lower type (%s) in the rest of the %d sample rows\n"),
                              j+1, typeName[type[j]], sampleLines);
diff --git a/src/fread.h b/src/fread.h
index 446da18e4..7035615a5 100644
--- a/src/fread.h
+++ b/src/fread.h
@@ -20,7 +20,8 @@
 typedef enum {
   NEG = -1,        // dummy to force signed type; sign bit used for out-of-sample type bump management
   CT_DROP = 0,     // skip column requested by user; it is navigated as a string column with the prevailing quoteRule
-  CT_BOOL8_N,      // int8_t; first enum value must be 1 not 0(=CT_DROP) so that it can be negated to -1.
+  CT_EMPTY,        // int8_t; first enum value must be 1 not 0(=CT_DROP) so that it can be negated to -1. EMPTY to help column heading guess, #5257
+  CT_BOOL8_N,      // int8_t
   CT_BOOL8_U,
   CT_BOOL8_T,
   CT_BOOL8_L,
diff --git a/src/freadR.c b/src/freadR.c
index 97fe691aa..82992aba3 100644
--- a/src/freadR.c
+++ b/src/freadR.c
@@ -24,9 +24,9 @@ Secondary separator for list() columns, such as columns 11 and 12 in BED (no nee
 
 #define NUT  NUMTYPE+2  // +1 for "numeric" alias for "double"; +1 for CLASS fallback using as.class() at R level afterwards
 
-static int  typeSxp[NUT] =     {NILSXP,  LGLSXP,     LGLSXP,     LGLSXP,     LGLSXP,     INTSXP,    REALSXP,     REALSXP,    REALSXP,        REALSXP,        INTSXP,          REALSXP,         STRSXP,      REALSXP,    STRSXP   };
-static char typeRName[NUT][10]={"NULL",  "logical",  "logical",  "logical",  "logical",  "integer", "integer64", "double",   "double",       "double",       "IDate",         "POSIXct",       "character", "numeric",  "CLASS"  };
-static int  typeEnum[NUT] =    {CT_DROP, CT_BOOL8_N, CT_BOOL8_U, CT_BOOL8_T, CT_BOOL8_L, CT_INT32,  CT_INT64,    CT_FLOAT64, CT_FLOAT64_HEX, CT_FLOAT64_EXT, CT_ISO8601_DATE, CT_ISO8601_TIME, CT_STRING,   CT_FLOAT64, CT_STRING};
+static int  typeSxp[NUT] =     {NILSXP,  LGLSXP,    LGLSXP,     LGLSXP,     LGLSXP,     LGLSXP,     INTSXP,    REALSXP,     REALSXP,    REALSXP,        REALSXP,        INTSXP,          REALSXP,         STRSXP,      REALSXP,    STRSXP   };
+static char typeRName[NUT][10]={"NULL",  "logical", "logical",  "logical",  "logical",  "logical",  "integer", "integer64", "double",   "double",       "double",       "IDate",         "POSIXct",       "character", "numeric",  "CLASS"  };
+static int  typeEnum[NUT] =    {CT_DROP, CT_EMPTY,  CT_BOOL8_N, CT_BOOL8_U, CT_BOOL8_T, CT_BOOL8_L, CT_INT32,  CT_INT64,    CT_FLOAT64, CT_FLOAT64_HEX, CT_FLOAT64_EXT, CT_ISO8601_DATE, CT_ISO8601_TIME, CT_STRING,   CT_FLOAT64, CT_STRING};
 static colType readInt64As=CT_INT64;
 static SEXP selectSxp;
 static SEXP dropSxp;