diff --git a/R/col_count_match.R b/R/col_count_match.R
index 1daac946b..6e5a82fe4 100644
--- a/R/col_count_match.R
+++ b/R/col_count_match.R
@@ -300,15 +300,11 @@ col_count_match <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      create_autobrief(
-        agent = agent,
-        assertion_type = "col_count_match",
-        values = count
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    preconditions = preconditions, values = count,
+    assertion_type = "col_count_match"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns = "column", agent)
diff --git a/R/col_exists.R b/R/col_exists.R
index f56743db7..9edb8df80 100644
--- a/R/col_exists.R
+++ b/R/col_exists.R
@@ -278,10 +278,12 @@ col_exists <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-    brief <-
-      generate_autobriefs(agent, columns, preconditions, values, "col_exists")
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns,
+    preconditions = preconditions, values = value,
+    assertion_type = "col_exists"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -309,7 +311,7 @@ col_exists <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id[i],
         label = label[[i]],
-        brief = brief[i],
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/col_is_character.R b/R/col_is_character.R
index a56ed9bd1..459ffc3b9 100644
--- a/R/col_is_character.R
+++ b/R/col_is_character.R
@@ -269,12 +269,12 @@ col_is_character <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-    brief <-
-      generate_autobriefs(
-        agent, columns, preconditions, values, "col_is_character"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns,
+    preconditions = preconditions, values = value,
+    assertion_type = "col_is_character"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -302,7 +302,7 @@ col_is_character <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id[i],
         label = label[[i]],
-        brief = brief[i],
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/col_is_date.R b/R/col_is_date.R
index 5f9c91734..348901480 100644
--- a/R/col_is_date.R
+++ b/R/col_is_date.R
@@ -261,12 +261,12 @@ col_is_date <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-    brief <-
-      generate_autobriefs(
-        agent, columns, preconditions, values, "col_is_date"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns,
+    preconditions = preconditions, values = value,
+    assertion_type = "col_is_date"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -294,7 +294,7 @@ col_is_date <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id[i],
         label = label[[i]],
-        brief = brief[i],
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/col_is_factor.R b/R/col_is_factor.R
index b57b724c9..325be8d7f 100644
--- a/R/col_is_factor.R
+++ b/R/col_is_factor.R
@@ -267,12 +267,12 @@ col_is_factor <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-    brief <-
-      generate_autobriefs(
-        agent, columns, preconditions, values, "col_is_factor"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns,
+    preconditions = preconditions, values = value,
+    assertion_type = "col_is_factor"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -300,7 +300,7 @@ col_is_factor <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id[i],
         label = label[[i]],
-        brief = brief[i],
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/col_is_integer.R b/R/col_is_integer.R
index 9e7996d1a..b1645154c 100644
--- a/R/col_is_integer.R
+++ b/R/col_is_integer.R
@@ -265,12 +265,12 @@ col_is_integer <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-    brief <-
-      generate_autobriefs(
-        agent, columns, preconditions, values, "col_is_integer"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns,
+    preconditions = preconditions, values = value,
+    assertion_type = "col_is_integer"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -298,7 +298,7 @@ col_is_integer <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id[i],
         label = label[[i]],
-        brief = brief[i],
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/col_is_logical.R b/R/col_is_logical.R
index 215d7a8f7..f9029bee0 100644
--- a/R/col_is_logical.R
+++ b/R/col_is_logical.R
@@ -262,12 +262,12 @@ col_is_logical <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-    brief <-
-      generate_autobriefs(
-        agent, columns, preconditions, values, "col_is_logical"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns,
+    preconditions = preconditions, values = value,
+    assertion_type = "col_is_logical"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -295,7 +295,7 @@ col_is_logical <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id[i],
         label = label[[i]],
-        brief = brief[i],
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/col_is_numeric.R b/R/col_is_numeric.R
index b53711743..3951456a8 100644
--- a/R/col_is_numeric.R
+++ b/R/col_is_numeric.R
@@ -262,12 +262,12 @@ col_is_numeric <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-    brief <-
-      generate_autobriefs(
-        agent, columns, preconditions, values, "col_is_numeric"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns,
+    preconditions = preconditions, values = value,
+    assertion_type = "col_is_numeric"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -295,7 +295,7 @@ col_is_numeric <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id[i],
         label = label[[i]],
-        brief = brief[i],
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/col_is_posix.R b/R/col_is_posix.R
index 8786163e2..aaa20af7a 100644
--- a/R/col_is_posix.R
+++ b/R/col_is_posix.R
@@ -262,12 +262,12 @@ col_is_posix <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-    brief <-
-      generate_autobriefs(
-        agent, columns, preconditions, values, "col_is_posix"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns,
+    preconditions = preconditions, values = value,
+    assertion_type = "col_is_posix"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -295,7 +295,7 @@ col_is_posix <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id[i],
         label = label[[i]],
-        brief = brief[i],
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/col_schema_match.R b/R/col_schema_match.R
index 51bae99b2..cbc95c45a 100644
--- a/R/col_schema_match.R
+++ b/R/col_schema_match.R
@@ -356,14 +356,10 @@ col_schema_match <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      create_autobrief(
-        agent = agent,
-        assertion_type = "col_schema_match"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    assertion_type = "col_schema_match"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns = "column", agent)
diff --git a/R/col_vals_between.R b/R/col_vals_between.R
index 8e21cf63e..857a21346 100644
--- a/R/col_vals_between.R
+++ b/R/col_vals_between.R
@@ -433,17 +433,12 @@ col_vals_between <- function(
   left <- as.list(left)
   right <- as.list(right)
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = c(left, right),
-        assertion_type = "col_vals_between"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = c(left, right),
+    assertion_type = "col_vals_between"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -480,7 +475,7 @@ col_vals_between <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_decreasing.R b/R/col_vals_decreasing.R
index 3feddc6ae..1393f106d 100644
--- a/R/col_vals_decreasing.R
+++ b/R/col_vals_decreasing.R
@@ -413,17 +413,12 @@ col_vals_decreasing <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = increasing_tol,
-        assertion_type = "col_vals_decreasing"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = increasing_tol,
+    assertion_type = "col_vals_decreasing"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -460,7 +455,7 @@ col_vals_decreasing <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_equal.R b/R/col_vals_equal.R
index a56a9a081..c30a22a48 100644
--- a/R/col_vals_equal.R
+++ b/R/col_vals_equal.R
@@ -365,17 +365,12 @@ col_vals_equal <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = value,
-        assertion_type = "col_vals_equal"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = value,
+    assertion_type = "col_vals_equal"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -412,7 +407,7 @@ col_vals_equal <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_expr.R b/R/col_vals_expr.R
index 8c23b642a..a2d788613 100644
--- a/R/col_vals_expr.R
+++ b/R/col_vals_expr.R
@@ -367,14 +367,12 @@ col_vals_expr <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      create_autobrief(
-        agent = agent,
-        assertion_type = "col_vals_expr"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    segments_list = segments_list,
+    preconditions = preconditions,
+    assertion_type = "col_vals_expr"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns = "column", agent)
@@ -409,7 +407,7 @@ col_vals_expr <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id,
         label = label[[i]],
-        brief = brief,
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/col_vals_gt.R b/R/col_vals_gt.R
index 731dc219b..2f21986be 100644
--- a/R/col_vals_gt.R
+++ b/R/col_vals_gt.R
@@ -487,17 +487,12 @@ col_vals_gt <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = value,
-        assertion_type = "col_vals_gt"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = value,
+    assertion_type = "col_vals_gt"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -534,7 +529,7 @@ col_vals_gt <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_gte.R b/R/col_vals_gte.R
index 16642ef39..3474c3bc0 100644
--- a/R/col_vals_gte.R
+++ b/R/col_vals_gte.R
@@ -364,17 +364,12 @@ col_vals_gte <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = value,
-        assertion_type = "col_vals_gte"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = value,
+    assertion_type = "col_vals_gte"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -411,7 +406,7 @@ col_vals_gte <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_in_set.R b/R/col_vals_in_set.R
index 2a68dd114..47ac6b989 100644
--- a/R/col_vals_in_set.R
+++ b/R/col_vals_in_set.R
@@ -357,17 +357,12 @@ col_vals_in_set <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = set,
-        assertion_type = "col_vals_in_set"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = set,
+    assertion_type = "col_vals_in_set"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -403,7 +398,7 @@ col_vals_in_set <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_increasing.R b/R/col_vals_increasing.R
index bd38c09cf..04d6c36dc 100644
--- a/R/col_vals_increasing.R
+++ b/R/col_vals_increasing.R
@@ -401,17 +401,12 @@ col_vals_increasing <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = decreasing_tol,
-        assertion_type = "col_vals_increasing"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = decreasing_tol,
+    assertion_type = "col_vals_increasing"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -448,7 +443,7 @@ col_vals_increasing <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_lt.R b/R/col_vals_lt.R
index 85c05f186..065199174 100644
--- a/R/col_vals_lt.R
+++ b/R/col_vals_lt.R
@@ -366,17 +366,12 @@ col_vals_lt <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = value,
-        assertion_type = "col_vals_lt"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = value,
+    assertion_type = "col_vals_lt"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -413,7 +408,7 @@ col_vals_lt <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_lte.R b/R/col_vals_lte.R
index c99ec088a..6b912defe 100644
--- a/R/col_vals_lte.R
+++ b/R/col_vals_lte.R
@@ -367,17 +367,12 @@ col_vals_lte <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = value,
-        assertion_type = "col_vals_lte"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = value,
+    assertion_type = "col_vals_lte"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -414,7 +409,7 @@ col_vals_lte <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_make_set.R b/R/col_vals_make_set.R
index 76700243d..3eb946bc8 100644
--- a/R/col_vals_make_set.R
+++ b/R/col_vals_make_set.R
@@ -359,17 +359,12 @@ col_vals_make_set <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = set,
-        assertion_type = "col_vals_make_set"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = set,
+    assertion_type = "col_vals_make_set"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -405,7 +400,7 @@ col_vals_make_set <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_make_subset.R b/R/col_vals_make_subset.R
index a5b34c455..7e2763169 100644
--- a/R/col_vals_make_subset.R
+++ b/R/col_vals_make_subset.R
@@ -356,17 +356,12 @@ col_vals_make_subset <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = set,
-        assertion_type = "col_vals_make_subset"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = set,
+    assertion_type = "col_vals_make_subset"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -402,7 +397,7 @@ col_vals_make_subset <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_not_between.R b/R/col_vals_not_between.R
index a21f2749c..4252f671e 100644
--- a/R/col_vals_not_between.R
+++ b/R/col_vals_not_between.R
@@ -432,22 +432,16 @@ col_vals_not_between <- function(
   agent <- x
 
   # Avoid rlang (>= 0.3.0) soft deprecation warning
-  # Quosure lists can't be concatenated with objects other than quosures
-
+  # Quosure lists can't be concatenated with objects other than quosures.
   left <- as.list(left)
   right <- as.list(right)
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = c(left, right),
-        assertion_type = "col_vals_not_between"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = c(left, right),
+    assertion_type = "col_vals_not_between"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -484,7 +478,7 @@ col_vals_not_between <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_not_equal.R b/R/col_vals_not_equal.R
index a9062d14f..b911c7072 100644
--- a/R/col_vals_not_equal.R
+++ b/R/col_vals_not_equal.R
@@ -364,17 +364,12 @@ col_vals_not_equal <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = value,
-        assertion_type = "col_vals_not_equal"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = value,
+    assertion_type = "col_vals_not_equal"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -411,7 +406,7 @@ col_vals_not_equal <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_not_in_set.R b/R/col_vals_not_in_set.R
index f40c93deb..6322d79c9 100644
--- a/R/col_vals_not_in_set.R
+++ b/R/col_vals_not_in_set.R
@@ -353,17 +353,12 @@ col_vals_not_in_set <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = set,
-        assertion_type = "col_vals_not_in_set"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = set,
+    assertion_type = "col_vals_not_in_set"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -399,7 +394,7 @@ col_vals_not_in_set <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_not_null.R b/R/col_vals_not_null.R
index 175d6f326..e173d3144 100644
--- a/R/col_vals_not_null.R
+++ b/R/col_vals_not_null.R
@@ -343,17 +343,12 @@ col_vals_not_null <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = values,
-        assertion_type = "col_vals_not_null"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = values,
+    assertion_type = "col_vals_not_null"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -388,7 +383,7 @@ col_vals_not_null <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_null.R b/R/col_vals_null.R
index 11bc5938f..3b760d13e 100644
--- a/R/col_vals_null.R
+++ b/R/col_vals_null.R
@@ -342,17 +342,12 @@ col_vals_null <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = values,
-        assertion_type = "col_vals_null"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = values,
+    assertion_type = "col_vals_null"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -387,7 +382,7 @@ col_vals_null <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_regex.R b/R/col_vals_regex.R
index 3f6a6bbf7..6b5ff4148 100644
--- a/R/col_vals_regex.R
+++ b/R/col_vals_regex.R
@@ -358,17 +358,12 @@ col_vals_regex <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = regex,
-        assertion_type = "col_vals_regex"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = regex,
+    assertion_type = "col_vals_regex"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -405,7 +400,7 @@ col_vals_regex <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/col_vals_within_spec.R b/R/col_vals_within_spec.R
index 945ba4e1c..e9061a64e 100644
--- a/R/col_vals_within_spec.R
+++ b/R/col_vals_within_spec.R
@@ -423,17 +423,12 @@ col_vals_within_spec <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      generate_autobriefs(
-        agent = agent,
-        columns = columns,
-        preconditions = preconditions,
-        values = spec,
-        assertion_type = "col_vals_within_spec"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions, values = spec,
+    assertion_type = "col_vals_within_spec"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns, agent)
@@ -470,7 +465,7 @@ col_vals_within_spec <- function(
           actions = covert_actions(actions, agent),
           step_id = step_id[i],
           label = label[[i, j]],
-          brief = brief[i],
+          brief = brief[[i, j]],
           active = active
         )
     }
diff --git a/R/conjointly.R b/R/conjointly.R
index b6c44f39d..ff398d741 100644
--- a/R/conjointly.R
+++ b/R/conjointly.R
@@ -401,16 +401,12 @@ conjointly <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      create_autobrief(
-        agent = agent,
-        assertion_type = "conjointly",
-        preconditions = preconditions,
-        values = validation_formulas
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    segments_list = segments_list,
+    preconditions = preconditions, values = validation_formulas,
+    assertion_type = "conjointly"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns = "column", agent)
@@ -446,7 +442,7 @@ conjointly <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id,
         label = label[[i]],
-        brief = brief,
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/row_count_match.R b/R/row_count_match.R
index 8e3dc5156..ee55cec1a 100644
--- a/R/row_count_match.R
+++ b/R/row_count_match.R
@@ -362,15 +362,12 @@ row_count_match <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      create_autobrief(
-        agent = agent,
-        assertion_type = "row_count_match",
-        values = count
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    segments_list = segments_list,
+    preconditions = preconditions, values = count,
+    assertion_type = "row_count_match"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns = "column", agent)
@@ -405,7 +402,7 @@ row_count_match <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id,
         label = label[[i]],
-        brief = brief,
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/rows_complete.R b/R/rows_complete.R
index f081b37f5..de3ba6b85 100644
--- a/R/rows_complete.R
+++ b/R/rows_complete.R
@@ -333,15 +333,12 @@ rows_complete <- function(
     columns <- paste(columns, collapse = ", ")
   }
 
-  if (is.null(brief)) {
-
-    brief <-
-      create_autobrief(
-        agent = agent,
-        assertion_type = "rows_complete",
-        column = columns
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions,
+    assertion_type = "rows_complete"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns = "column", agent)
@@ -376,7 +373,7 @@ rows_complete <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id,
         label = label[[i]],
-        brief = brief,
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/rows_distinct.R b/R/rows_distinct.R
index 9298078f4..267e28dd4 100644
--- a/R/rows_distinct.R
+++ b/R/rows_distinct.R
@@ -334,15 +334,12 @@ rows_distinct <- function(
     columns <- paste(columns, collapse = ", ")
   }
 
-  if (is.null(brief)) {
-
-    brief <-
-      create_autobrief(
-        agent = agent,
-        assertion_type = "rows_distinct",
-        column = columns
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    columns = columns, segments_list = segments_list,
+    preconditions = preconditions,
+    assertion_type = "rows_distinct"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns = "column", agent)
@@ -377,7 +374,7 @@ rows_distinct <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id,
         label = label[[i]],
-        brief = brief,
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/serially.R b/R/serially.R
index b432e4858..8ba63a524 100644
--- a/R/serially.R
+++ b/R/serially.R
@@ -682,7 +682,7 @@ serially <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id,
         label = label[[i]],
-        brief = brief,
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/specially.R b/R/specially.R
index 368ede097..691cc5532 100644
--- a/R/specially.R
+++ b/R/specially.R
@@ -356,14 +356,12 @@ specially <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      create_autobrief(
-        agent = agent,
-        assertion_type = "specially"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    segments_list = segments_list,
+    preconditions = preconditions,
+    assertion_type = "specially"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns = "column", agent)
@@ -399,7 +397,7 @@ specially <- function(
         actions = covert_actions(actions, agent),
         step_id = step_id,
         label = label[[i]],
-        brief = brief,
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/tbl_match.R b/R/tbl_match.R
index 7360d9291..b1249c475 100644
--- a/R/tbl_match.R
+++ b/R/tbl_match.R
@@ -334,14 +334,12 @@ tbl_match <- function(
 
   agent <- x
 
-  if (is.null(brief)) {
-
-    brief <-
-      create_autobrief(
-        agent = agent,
-        assertion_type = "tbl_match"
-      )
-  }
+  brief <- resolve_brief(
+    brief = brief, agent = agent,
+    segments_list = segments_list,
+    preconditions = preconditions,
+    assertion_type = "tbl_match"
+  )
 
   # Normalize any provided `step_id` value(s)
   step_id <- normalize_step_id(step_id, columns = "column", agent)
@@ -374,8 +372,8 @@ tbl_match <- function(
         seg_val = seg_val,
         actions = covert_actions(actions, agent),
         step_id = step_id,
-        label = label,
-        brief = brief,
+        label = label[[i]],
+        brief = brief[[i]],
         active = active
       )
   }
diff --git a/R/utils.R b/R/utils.R
index 2c87a1dbf..dae88b117 100644
--- a/R/utils.R
+++ b/R/utils.R
@@ -238,7 +238,43 @@ is_secret_agent <- function(x) {
   is_ptblank_agent(x) && (x$label == "::QUIET::")
 }
 
-resolve_label <- function(label, columns = "", segments = "") {
+resolve_brief <- function(brief, agent,
+                          columns = list(NULL), segments_list = list(NULL),
+                          preconditions = NULL, values = NULL,
+                          assertion_type) {
+
+  n_columns <- length(columns)
+  n_segments <- length(segments_list)
+  n_combinations <- n_columns * n_segments
+
+  # If missing, apply auto-brief
+  if (is.null(brief)) {
+    brief <- generate_autobriefs(
+      agent = agent, columns = columns,
+      preconditions = preconditions, values = values,
+      assertion_type = assertion_type
+    )
+    # auto-brief is generated once per column - need to recycle by segment
+    brief <- rep(brief, each = n_segments)
+  }
+
+  # Brief must be a single string or matched in length
+  if (!length(brief) %in% c(1L, n_combinations)) {
+    cli::cli_abort(paste0(
+      "`brief` must be length 1",
+      if (n_combinations != 1L) " or {n_combinations}",
+      ", not {length(brief)}."
+    ))
+  }
+
+  # Recycle the string
+  brief <- rep_len(brief, n_combinations)
+  # Return packed vector/matrix for iteration over steps
+  pack_by_col_seg(brief, n_columns, n_segments,  c(columns, segments))
+
+}
+
+resolve_label <- function(label, columns = list(NULL), segments = list(NULL)) {
   n_columns <- length(columns)
   n_segments <- length(segments)
   n_combinations <- n_columns * n_segments
@@ -246,23 +282,29 @@ resolve_label <- function(label, columns = "", segments = "") {
   if (is.null(label)) {
     label <- NA_character_
   }
-  # If length-1, match length of col-x-seg combination
-  if (length(label) == 1) {
-    label <- rep_len(label, n_combinations)
+  # Label must be a single string or matched in length
+  if (!length(label) %in% c(1L, n_combinations)) {
+    cli::cli_abort(paste0(
+      "`label` must be length 1",
+      if (n_combinations != 1L) " or {n_combinations}",
+      ", not {length(label)}."
+    ))
   }
-  # Check for length match
-  if (length(label) != n_combinations) {
-    rlang::abort(paste0("`label` must be length 1 or ", n_combinations,
-                        ", not ", length(label)))
-  }
-  # Create a columns * segments matrix of the (recycled) label vector
-  # - Fill by row to preserve order (for loops iterate the j before the i)
-  out <- matrix(label, nrow = n_columns, ncol = n_segments, byrow = TRUE)
+  # Recycle the string
+  label <- rep_len(label, n_combinations)
+  # Return packed vector/matrix for iteration over steps
+  pack_by_col_seg(label, n_columns, n_segments, c(columns, segments))
+}
+
+# Create a columns * segments matrix/vector for an input (ex: `brief`, `label`)
+# - Subsettable via `out[col]`, `out[seg]`, or `out[col,seg]`
+pack_by_col_seg <- function(x, n_columns, n_segments, packed_dim) {
+  # Fill by row to preserve order (for loops iterate the j before the i)
+  out <- matrix(x, nrow = n_columns, ncol = n_segments, byrow = TRUE)
   # If missing columns and/or segments, collapse to vector/scalar
-  if (missing(columns) || missing(segments)) {
+  if (any(lengths(packed_dim) == 0)) {
     out <- as.vector(out)
   }
-  # A matrix/vector subsettable via `out[col]`, `out[seg]`, or `out[col,seg]`
   out
 }
 
diff --git a/tests/testthat/test-brief.R b/tests/testthat/test-brief.R
new file mode 100644
index 000000000..f422b9bcf
--- /dev/null
+++ b/tests/testthat/test-brief.R
@@ -0,0 +1,229 @@
+test_that("`brief` recycles when possible", {
+
+  agent <- create_agent(small_table)
+  get_briefs <- function(x) x$validation_set$brief
+
+  expect_length(
+    agent %>%
+      col_exists(c("a", "b"), brief = NULL) %>%
+      get_briefs(),
+    2L
+  )
+
+  expect_identical(
+    agent %>%
+      col_exists(c("a", "b"), brief = NA) %>%
+      get_briefs(),
+    c(NA_character_, NA_character_)
+  )
+
+  expect_identical(
+    agent %>%
+      col_exists(c("a", "b"), brief = c("x", NA)) %>%
+      get_briefs(),
+    c("x", NA_character_)
+  )
+
+  expect_equal(
+    agent %>%
+      col_exists(c("a", "b"), brief = "one") %>%
+      get_briefs(),
+    c("one", "one")
+  )
+
+  expect_equal(
+    agent %>%
+      col_exists(c("a", "b"), brief = c("one", "two")) %>%
+      get_briefs(),
+    c("one", "two")
+  )
+
+  expect_error(
+    agent %>%
+      col_vals_equal(
+        c("a", "b"), 0,
+        segments = vars(f),
+        brief = c("one", "two", "three")
+    ),
+    "must be length 1 or 6, not 3"
+  )
+
+  expect_error(
+    agent %>%
+      col_exists("a", brief = c("one", "two")),
+    "must be length 1, not 2"
+  )
+
+})
+
+test_that("Briefs batch tests", {
+
+  validation_fns <- all_validations_fns_vec()
+  validation_fns <- setdiff(validation_fns, c("serially", "conjointly", "specially"))
+  validation_fns <- mget(validation_fns, asNamespace("pointblank"))
+  validation_fn_args <- sapply(validation_fns, function(x) {
+    paste(intersect(names(formals(x)), c("segments", "columns")), collapse = "+")
+  })
+  validation_fn_args <- validation_fn_args[validation_fn_args != ""]
+  validation_fn_args[grepl(x = names(validation_fn_args), "^rows_")] <- "rows_*"
+  table(validation_fn_args)
+
+  agent <- create_agent(small_table)
+  test_multi_briefs <- function(f, ...) {
+    test <- validation_fn_args[[f]]
+    f <- validation_fns[[f]]
+    cols <- c("a", "b")
+    segs <- c("high", "low", "mid")
+    switch(test,
+      "columns" = {
+        out <- cols
+        agent <- agent %>%
+          f(columns = c("a", "b"), ..., brief = cols) # 2-steps
+      },
+      "segments" = {
+        out <- segs
+        agent <- agent %>%
+          f(segments = vars(f), ..., brief = segs) # 3-steps
+      }, "columns+segments" = {
+        out <- as.vector(outer(segs, cols, function(s, c) paste0(c, ":", s)))
+        agent <- agent %>%
+          f(columns = c("a", "b"), segments = vars(f), ..., brief = out) # 6-steps
+      }, "rows_*" = {
+        out <- segs
+        agent <- agent %>%
+          f(columns = c("a", "b"), segments = vars(f), ..., brief = segs) # 3-steps
+      }
+    )
+    if (rlang::is_interactive()) print(agent)
+    expect_identical(out, agent$validation_set$brief)
+  }
+
+  # columns
+  test_multi_briefs("col_is_character")
+  test_multi_briefs("col_is_numeric")
+  test_multi_briefs("col_is_integer")
+  test_multi_briefs("col_is_logical")
+  test_multi_briefs("col_is_date")
+  test_multi_briefs("col_is_posix")
+  test_multi_briefs("col_is_factor")
+  test_multi_briefs("col_exists")
+
+  # columns + segments
+  test_multi_briefs("col_vals_lt", value = 5)
+  test_multi_briefs("col_vals_lte", value = 5)
+  test_multi_briefs("col_vals_equal", value = 5)
+  test_multi_briefs("col_vals_not_equal", value = 5)
+  test_multi_briefs("col_vals_gte", value = 5)
+  test_multi_briefs("col_vals_gt", value = 5)
+  test_multi_briefs("col_vals_between", left = 2, right = 5)
+  test_multi_briefs("col_vals_not_between", left = 2, right = 5)
+  test_multi_briefs("col_vals_in_set", set = c(2, 5))
+  test_multi_briefs("col_vals_not_in_set", set = c(2, 5))
+  test_multi_briefs("col_vals_make_set", set = c(2, 5))
+  test_multi_briefs("col_vals_make_subset", set = c(2, 5))
+  test_multi_briefs("col_vals_null")
+  test_multi_briefs("col_vals_not_null")
+  test_multi_briefs("col_vals_increasing")
+  test_multi_briefs("col_vals_decreasing")
+  test_multi_briefs("col_vals_regex", regex = "abc")
+  test_multi_briefs("col_vals_within_spec", spec = "email")
+
+  # segments
+  test_multi_briefs("col_vals_expr", expr = expr(a %% 1 == 0))
+  test_multi_briefs("row_count_match", count = small_table)
+  test_multi_briefs("tbl_match", tbl_compare = small_table)
+
+  # rows_*
+  test_multi_briefs("rows_distinct")
+  test_multi_briefs("rows_complete")
+
+})
+
+test_that("Briefs batch tests: special validations", {
+
+  agent <- create_agent(small_table)
+  get_briefs <- function(x) x$validation_set$brief
+
+  # Special: serially
+  expect_identical(
+    agent %>%
+      serially(
+        ~ test_col_vals_lt(., columns = a, value = 8),
+        ~ test_col_vals_gt(., columns = c, value = vars(a)),
+        ~ col_vals_not_null(., columns = b),
+        preconditions = ~ . %>% dplyr::filter(a < 10),
+        actions = action_levels(warn_at = 0.1, stop_at = 0.2),
+        label = "The `serially()` step.",
+        active = FALSE,
+        brief = "custom brief"
+      ) %>%
+      get_briefs()
+    ,
+    "custom brief"
+  )
+
+  # Special: specially
+  expect_identical(
+    agent %>%
+      specially(
+        fn = function(x) { ... },
+        preconditions = ~ . %>% dplyr::filter(a < 10),
+        actions = action_levels(warn_at = 0.1, stop_at = 0.2),
+        label = "The `specially()` step.",
+        active = FALSE,
+        brief = "custom brief"
+      ) %>%
+      get_briefs()
+    ,
+    "custom brief"
+  )
+
+  # Special: conjointly (no segments)
+  expect_identical(
+    agent %>%
+      conjointly(
+        ~ col_vals_lt(., columns = a, value = 8),
+        ~ col_vals_gt(., columns = c, value = vars(a)),
+        ~ col_vals_not_null(., columns = b),
+        preconditions = ~ . %>% dplyr::filter(a < 10),
+        # segments = b ~ c("group_1", "group_2"),
+        actions = action_levels(warn_at = 0.1, stop_at = 0.2),
+        label = "The `conjointly()` step.",
+        active = FALSE,
+        brief = "custom brief"
+      ) %>%
+      get_briefs(),
+    "custom brief"
+  )
+
+  # Special: conjointly (expanded with segments)
+  expect_identical(
+    agent %>%
+      conjointly(
+        ~ col_vals_lt(., columns = a, value = 8),
+        ~ col_vals_gt(., columns = c, value = vars(a)),
+        ~ col_vals_not_null(., columns = b),
+        preconditions = ~ . %>% dplyr::filter(a < 10),
+        segments = b ~ c("group_1", "group_2"),
+        actions = action_levels(warn_at = 0.1, stop_at = 0.2),
+        label = "The `conjointly()` step.",
+        active = FALSE,
+        brief = "custom brief constant"
+      ) %>%
+      conjointly(
+        ~ col_vals_lt(., columns = a, value = 8),
+        ~ col_vals_gt(., columns = c, value = vars(a)),
+        ~ col_vals_not_null(., columns = b),
+        preconditions = ~ . %>% dplyr::filter(a < 10),
+        segments = b ~ c("group_1", "group_2"),
+        actions = action_levels(warn_at = 0.1, stop_at = 0.2),
+        label = "The `conjointly()` step.",
+        active = FALSE,
+        brief = c("custom brief multi1", "custom brief multi2")
+      ) %>%
+      get_briefs(),
+    c("custom brief constant", "custom brief constant",
+      "custom brief multi1", "custom brief multi2")
+  )
+
+})